5α-acetamido-6β-hydroxycholestan-3β-yl acetate | 21549-41-7

• 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: 5α-acetamido-6β-hydroxycholestan-3β-yl acetate
• 英文别名: [(3S,5R,6R,8S,9S,10R,13R,14S,17R)-5-acetamido-6-hydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,3,4,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-yl] acetate
• CAS: 21549-41-7
• 化学式: C₃₁H₅₃NO₄
• 分子量: 503.766
• InChiKey: ZQOXHAOQKWQSPY-ZJBXHLDWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  乙腈 、 5,6-β-epoxycholesteryl acetate 在 Starbon₄₀₀-HSO₃ 作用下， 反应 11.0h， 以98%的产率得到5α-acetamido-6β-hydroxycholestan-3β-yl acetate
  参考文献：
  名称：

  Starbon®400-HSO3: A green mesoporous carbonaceous solid acid catalyst for the Ritter reaction

  摘要：

  The application of the Starbon (R) Technology in the Ritter reaction to afford vic-N-acylamino-hydroxy compounds, in very high yields, is reported. Starbon (R) 400-HSO3 was used as a green and easily recovered mesoporous carbonaceous solid add catalyst and applied, for the first time, to more complex naturally-derived substrates, such as steroids. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.catcom.2015.06.010

文献信息

• Bismuth(III) salt-catalyzed Westphalen and “backbone” rearrangements of 5β,6β-epoxysteroids
  作者：Rui M.A. Pinto、Jorge A.R. Salvador、Christophe Le Roux、Rui A. Carvalho、Manuela Ramos Silva、Ana Matos Beja、José A. Paixão

  DOI：10.1016/j.steroids.2008.01.006

  日期：2008.5

  bismuth(III) salts as catalysts for the Westphalen and "backbone" rearrangements of 5 beta,6 beta-epoxysteroids is reported. This method is particularly sensitive to changes on solvent, temperature, stereochemistry of starting epoxysteroid, and its substituent at C17. Depending on the reaction conditions, either Westphalen-type or "backbone" rearranged products were obtained, all being 3 beta-acetoxy-6 beta

  报道了一种使用“生态友好型”铋（III）盐作为催化剂的5β，6β-环氧甾类化合物的威斯特伐伦和“骨架”重排的新工艺。此方法对溶剂，温度，起始环氧类固醇的立体化学及其在C17处的取代基的变化特别敏感。取决于反应条件，获得了威斯特伐伦型或“骨架”重排的产物，所有产物均被3β-乙酰氧基-6β-羟基取代。获得了几种新的烯烃类19-nor和18,19-dinorsteroids，并使用2D NMR和X射线晶体学技术完全完成了其结构解析。