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MedKoo Cat#: 145564 | Name: Daphenylline

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Daphenylline is a hexacyclic Daphniphyllum alkaloid. DAPHENYLLINE contains a complex cagelike backbone.

Chemical Structure

Daphenylline
Daphenylline
CAS#1152598-44-1

Theoretical Analysis

MedKoo Cat#: 145564

Name: Daphenylline

CAS#: 1152598-44-1

Chemical Formula: C21H27N

Exact Mass: 293.2100

Molecular Weight: 293.45

Elemental Analysis: C, 85.95; H, 9.27; N, 4.77

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Daphenylline;
IUPAC/Chemical Name
(2R,3S,6aS,8aS,12aS,12bR)-3,12a-dimethyl-1,2,3,4,6a,7,8,8a,9,10,12a,12b-dodecahydro-6H-2,12,11-(epiprop[2]en[3]yl[1,1]diylidene)azuleno[5,6-a]indolizine
InChi Key
FRNKVSPOMBSICI-XRRJANCQSA-N
InChi Code
1S/C21H27N/c1-12-10-22-11-15-7-5-13-3-4-14-6-8-16-17(12)9-18(22)21(15,2)20(16)19(13)14/h6,8,12-13,15,17-18H,3-5,7,9-11H2,1-2H3/t12-,13-,15-,17?,18-,21-/m1/s1
SMILES Code
[H][C@]12CCC3=C1C4=C(C=C3)[C@@H]5C[C@H]6[N@](C[C@@]([H])(CC2)[C@@]46C)C[C@H]5C
Appearance
To be determined
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 -4 C for short term (days to weeks) or -20 C for long term(months to years).
Solubility
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 293.45 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Xu B, Wang B, Xun W, Qiu FG. Total Synthesis of (-)-Daphenylline. Angew Chem Int Ed Engl. 2019 Apr 16;58(17):5754-5757. doi: 10.1002/anie.201902268. Epub 2019 Mar 27. PMID: 30919545. 2: Wu BL, Yao JN, Long XX, Tan ZQ, Liang X, Feng L, Wei K, Yang YR. Enantioselective Total Synthesis of (-)-Daphenylline. J Am Chem Soc. 2024 Jan 17;146(2):1262-1268. doi: 10.1021/jacs.3c12741. Epub 2024 Jan 5. PMID: 38180776. 3: Yamada R, Adachi Y, Yokoshima S, Fukuyama T. Total Synthesis of (-)-Daphenylline. Angew Chem Int Ed Engl. 2016 May 10;55(20):6067-70. doi: 10.1002/anie.201601958. Epub 2016 Apr 8. PMID: 27062676. 4: Wright BA, Regni A, Chaisan N, Sarpong R. Navigating Excess Complexity: Total Synthesis of Daphenylline. J Am Chem Soc. 2024 Jan 24;146(3):1813-1818. doi: 10.1021/jacs.3c12953. Epub 2024 Jan 11. PMID: 38207289. 5: Cao MY, Ma BJ, Gu QX, Fu B, Lu HH. Concise Enantioselective Total Synthesis of Daphenylline Enabled by an Intramolecular Oxidative Dearomatization. J Am Chem Soc. 2022 Apr 6;144(13):5750-5755. doi: 10.1021/jacs.2c01674. Epub 2022 Mar 15. PMID: 35289615. 6: Chen X, Zhang HJ, Yang X, Lv H, Shao X, Tao C, Wang H, Cheng B, Li Y, Guo J, Zhang J, Zhai H. Divergent Total Syntheses of (-)-Daphnilongeranin B and (-)-Daphenylline. Angew Chem Int Ed Engl. 2018 Jan 22;57(4):947-951. doi: 10.1002/anie.201709762. Epub 2017 Dec 5. PMID: 29115009. 7: Wang B, Xu B, Xun W, Guo Y, Zhang J, Qiu FG. A General Strategy for the Construction of Calyciphylline A-Type Alkaloids: Divergent Total Syntheses of (-)-Daphenylline and (-)-Himalensine A. Angew Chem Int Ed Engl. 2021 Apr 19;60(17):9439-9443. doi: 10.1002/anie.202016212. Epub 2021 Mar 18. PMID: 33569888. 8: Zhang Q, Di YT, Li CS, Fang X, Tan CJ, Zhang Z, Zhang Y, He HP, Li SL, Hao XJ. Daphenylline, a new alkaloid with an unusual skeleton, from Daphniphyllum longeracemosum. Org Lett. 2009 Jun 4;11(11):2357-9. doi: 10.1021/ol9007958. PMID: 19438261. 9: Jansana S, Diaba F, Bonjoch J. Stereocontrolled Synthesis of the Daphenylline Pentacyclic ACDEF Ring System. Org Lett. 2019 Jul 19;21(14):5757-5761. doi: 10.1021/acs.orglett.9b02211. Epub 2019 Jul 2. PMID: 31264879. 10: Lu Z, Li Y, Deng J, Li A. Total synthesis of the Daphniphyllum alkaloid daphenylline. Nat Chem. 2013 Aug;5(8):679-84. doi: 10.1038/nchem.1694. Epub 2013 Jun 30. PMID: 23881499. 11: Chen Y, Zhang W, Ren L, Li J, Li A. Total Syntheses of Daphenylline, Daphnipaxianine A, and Himalenine D. Angew Chem Int Ed Engl. 2018 Jan 22;57(4):952-956. doi: 10.1002/anie.201711482. Epub 2017 Dec 21. PMID: 29193678. 12: Deng M, Yao Y, Li X, Li N, Zhang X, Liang G. Rapid Construction of the ABCE Tetracyclic Tertiary Amine Skeleton in Daphenylline Enabled by an Amine-Borane Complexation Strategy. Org Lett. 2019 May 3;21(9):3290-3294. doi: 10.1021/acs.orglett.9b01021. Epub 2019 Apr 22. PMID: 31008614. 13: Wang W, Li GP, Wang SF, Shi ZF, Cao XP. Direct and short construction of the ACDE ring system of daphenylline. Chem Asian J. 2015 Feb;10(2):377-82. doi: 10.1002/asia.201403152. Epub 2014 Nov 25. PMID: 25425355. 14: Li H, Qiu Y, Zhao C, Yuan Z, Xie X, She X. Diels-Alder/oxidative aromatization approach towards the all-carbon DEF tricyclic skeleton of daphenylline. Chem Asian J. 2014 May;9(5):1274-7. doi: 10.1002/asia.201400002. Epub 2014 Mar 3. PMID: 24591463. 15: Li H, Zheng J, Xu S, Ma D, Zhao C, Fang B, Xie X, She X. Rapid construction of the [6-6-6-5] tetracyclic skeleton of the Daphniphyllum alkaloid daphenylline. Chem Asian J. 2012 Nov;7(11):2519-22. doi: 10.1002/asia.201200625. Epub 2012 Sep 4. PMID: 22945890. 16: Fang B, Zheng H, Zhao C, Jing P, Li H, Xie X, She X. Synthesis of the tetracyclic core (ABCE rings) of daphenylline. J Org Chem. 2012 Sep 21;77(18):8367-73. doi: 10.1021/jo301533f. Epub 2012 Sep 10. PMID: 22934890.