6β-acetamido-5α-hydroxycholestan-3β-yl acetate | 38673-01-7

• 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: 6β-acetamido-5α-hydroxycholestan-3β-yl acetate
• 英文别名: 6-β-Acetamid-5α-cholestan-3β,5-diol-3-monoacetat；3β-acetoxy-6β-acetylamino-5α-cholestan-5-ol；6beta-Acetamido-5alpha-hydroxycholestan-3beta-yl acetate；[(3S,5R,6R,8S,9S,10R,13R,14S,17R)-6-acetamido-5-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: 38673-01-7
• 化学式: C₃₁H₅₃NO₄
• 分子量: 503.766
• InChiKey: NDMUWQREVLQSNV-ZJBXHLDWSA-N

物化性质

• 沸点：
  605.0±48.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

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

• 作为反应物：
  描述：

  6β-acetamido-5α-hydroxycholestan-3β-yl acetate 在 potassium hydrogencarbonate 作用下， 生成 6-β-Acetamid-5α-cholest-5-en-5-ol
  参考文献：
  名称：

  Kocovsky,P.; Cerny,V., Collection of Czechoslovak Chemical Communications, 1978, vol. 43, p. 1933 - 1941

  摘要：

  DOI：
• 作为产物：
  描述：

  乙腈 、 Acetic acid (3S,5R,6S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-20-oxa-cyclopropa[5,6]cyclopenta[a]phenanthren-3-yl ester 在 bismuth(III) bromide 作用下， 反应 16.0h， 以94%的产率得到6β-acetamido-5α-hydroxycholestan-3β-yl acetate
  参考文献：
  名称：

  Ritter Reaction Mediated by Bismuth(III) Salts: One-Step Conversion of ­Epoxides into vic-Acylamino-Hydroxy Compounds

  摘要：

  铋盐能促进环氧化物以极高的产率一步转化为沧酰氨基羟基化合物。

  DOI：

  10.1055/s-2006-949608

文献信息

• Starbon®400-HSO3: A green mesoporous carbonaceous solid acid catalyst for the Ritter reaction
  作者：Lígia M.M. Mesquita、Rui M.A. Pinto、Jorge A.R. Salvador、James H. Clark、Vitaliy L. Budarin

  DOI：10.1016/j.catcom.2015.06.010

  日期：2015.9

  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.
• Bismuth(III) salts mediated regioselective ring opening of epoxides: an easy route to halohydrins and β-hydroxy nitrates
  作者：Rui M.A. Pinto、Jorge A.R. Salvador、Christophe Le Roux

  DOI：10.1016/j.tet.2007.06.054

  日期：2007.9

  The ring opening of various epoxides was achieved under mild conditions using bismuth(III) salts. Halohydrins and beta-hydroxy nitrates were efficiently obtained from the corresponding 5 alpha,6 alpha-, 2 alpha,3 alpha-, and 5 beta,6 beta-epoxysteroid using BiCl3, BiBr3 or Bi(NO3)(3) center dot 5H2O. Considerations about the probable reaction mechanism are provided. 2D homo- and heteronuclear correlation NMR spectroscopic techniques were used to unequivocally demonstrate the trans-diaxial nature of the epoxide ring opening. (c) 2007 Elsevier Ltd. All rights reserved.
• Narayanan, C. R.; Landge, A. B., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 2, p. 299 - 302
  作者：Narayanan, C. R.、Landge, A. B.

  DOI：——

  日期：——