17β-methyl-20-oxo-18-nor-17α-pregna-5,13-diene-3β,16α-diyl diacetate | 5040-81-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 17β-methyl-20-oxo-18-nor-17α-pregna-5,13-diene-3β,16α-diyl diacetate
• 英文别名: 3β,16α-diacetoxy-17-methyl-18-nor-17βH-pregna-5,13-dien-20-one；3β,16α-Diacetoxy-17-methyl-18-nor-17βH-pregna-5,13-dien-20-on；3β,16α-Diacetoxy-17β-methyl-18-nor-17α-pregnadien-(5,13)-on-(20)；[(3S,8R,9S,10R,16R,17S)-17-acetyl-16-acetyloxy-10,17-dimethyl-2,3,4,7,8,9,11,12,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-yl] acetate
• CAS: 5040-81-3
• 化学式: C₂₅H₃₄O₅
• 分子量: 414.542
• InChiKey: CMMPQSVKMJZSAT-ZLBQLAPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  17β-methyl-20-oxo-18-nor-17α-pregna-5,13-diene-3β,16α-diyl diacetate 在 sodium tetrahydroborate 作用下， 生成 3β,16α-diacetoxy-17-methyl-18-nor-17βH-pregna-5,13-dien-20α_F-ol
  参考文献：
  名称：

  Achrem; Iljuchina, Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1969, p. 913,916, 917; engl. Ausg. S. 830, 832, 833

  摘要：

  DOI：
• 作为产物：
  描述：

  Acetic acid (S)-1-((3S,8R,9S,10R,16R,17S)-3-acetoxy-16-hydroxy-10,17-dimethyl-2,3,4,7,8,9,10,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)-ethyl ester 在 chromium(VI) oxide 作用下， 生成 17β-methyl-20-oxo-18-nor-17α-pregna-5,13-diene-3β,16α-diyl diacetate
  参考文献：
  名称：

  Transformed steroids

  摘要：

  DOI：

  10.1007/bf00907052

文献信息

• Bismuth(III) triflate-catalyzed rearrangement of 16α,17α-epoxy-20-oxosteroids. Synthesis and structural elucidation of new 16α-substituted 17α-alkyl-17β-methyl-Δ13-18-norsteroids
  作者：Rui M.A. Pinto、Jorge A.R. Salvador、Christophe Le Roux、Rui A. Carvalho、Ana Matos Beja、José A. Paixão

  DOI：10.1016/j.tet.2009.05.043

  日期：2009.8

  reagents, the reaction selectively affords the corresponding 16α-acyl rearranged products. The chemoselective rearrangement of 5β,6β;16α,17α-diepoxy-20-oxopregnan-3β-yl acetate to afford a ‘backbone’ rearranged product bearing the 16α,17α-epoxide group is also reported. Some mechanistic considerations are provided. All rearranged products were the subject of comprehensive structural elucidation, by

  据报道，三氟甲磺酸铋（III）用于重排16α，17α-环氧-20-氧类固醇。真正的催化条件下发生反应，得到新颖的17α -烷基- 17β甲基Δ 13 -18-也不轴承产品不同öC 16上的含取代基。当在不存在酰化剂的情况下进行反应时，获得异构体16α-和16β-羟基衍生物的混合物，而当在此类试剂的存在下进行时，反应选择性地提供相应的16α-酰基重排产物。还报道了5β，6β；16α，17α-双环氧-20-氧杂戊烷-3β-乙酸乙烯酯的化学选择性重排，以提供带有16α，17α-环氧基团的“骨架”重排产物。提供了一些机械方面的考虑。通过使用X射线晶体学和2D NMR，对所有重排产物进行了全面的结构阐明。
• Heussler; Wettstein, Chemische Berichte, 1954, vol. 87, p. 1301,1308
  作者：Heussler、Wettstein

  DOI：——

  日期：——
• Highly efficient Lewis acid catalyzed, one step conversions of 16α,17α-epoxy-3β-hydroxypregn-5-en-20-one to d-homosteroid and Δ13-steroids
  作者：Navdeep K Girdhar、M.P.S Ishar、Rajiv Kumar、Rajinder Singh、Gurmit Singh

  DOI：10.1016/s0040-4020(01)00673-1

  日期：2001.8

  Conversion of 16 alpha ,17 alpha -epoxy-3 beta -hydroxypregn-5-en-20-one (1a) to 16 beta -chloro-3 beta ,17 alpha -dihydroxy-17 beta -methyl-17a-homoandrost-5-en-17a-one (3) in very high yields (95%), in one step by treatment with 3 equiv. of anhyd. AlCl3, has been achieved; use of two equiv. of AlCl3 affords mixture Of D-homosteroid 3 (70%) and chlorohydrin 4 (27%). On the other hand, treatment of la with excess of acetic anhydride and anhydrous ZnCl2 at room temperature leads to reversal of the direction of epoxide ring opening with concomitant methyl migration, leading to 3 beta ,16 alpha -diacetoxy-17-methyl-17 alpha -pregna-5,13-diene-20-one (6) in high yield (92%). The conversions are a remarkable improvement over related routes in terms of both yield and selectivity. (C) 2001 Elsevier Science Ltd. All rights reserved.
• The Beckmann Rearrangement of the Acetoxime of Δ^5,16-Pregnadien-3β-o1-20-one Acetate with Boron Trifluoride
  作者：J. Romo、A. Romo de Vivar

  DOI：10.1021/ja01522a074

  日期：1959.7
• Wagner-Meerwein Rearrangements. III. Further Aspects of Acid-catalyzed Opening of Steroidal 16,17-Epoxides
  作者：Elliot L. Shapiro、Merl Steinberg、David Gould、Margaret Jevnik Gentles、Hershel L. Herzog、Marilyn Gilmore、William Charney、E. B. Hershberg、Leon Mandell

  DOI：10.1021/ja01533a038

  日期：1959.12