3β-acetoacetyloxy-5α-cholestane | 210537-92-1

• 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: 3β-acetoacetyloxy-5α-cholestane
• 英文别名: 3β-Acetoacetyloxy-5α-cholestan；[(3S,5S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl] 3-oxobutanoate
• CAS: 210537-92-1
• 化学式: C₃₁H₅₂O₃
• 分子量: 472.752
• InChiKey: OUVBVUVUDJWLQL-OPGMDCAGSA-N

物化性质

• 沸点：
  533.4±23.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.8
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-丁烯基溴 、 3β-acetoacetyloxy-5α-cholestane 在 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 96.0h， 生成 (E)-2-Acetyl-hex-4-enoic acid (3S,5S,8R,9S,10S,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester
  参考文献：
  名称：

  A convenient approach to chiral sulfoxides by enantioselective oxidation with a steroidal furylhydroperoxide

  摘要：

  The introduction of a steroidal residue into a position distant from the reaction center shows a beneficial effect on the reactivity of secondary furylhydroperoxides: chiral sulfoxides are obtained by asymmetric oxidation of sulfides and/or kinetic resolution of racemic sulfoxides with reduced reaction times and high enantiomeric excesses. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00163-3
• 作为产物：
  描述：

  3β-胆甾烷醇 、 乙酰乙酸乙酯 生成 3β-acetoacetyloxy-5α-cholestane
  参考文献：
  名称：

  Transesterification. I. β-Keto Esters

  摘要：

  DOI：

  10.1021/ja01153a045

文献信息

• Dissolving metal reduction of esters to alkanes. A method for the deoxygenation of alcohols
  作者：Anthony G. M. Barrett、Christopher R. A. Godfrey、David M. Hollinshead、Panayiotis A. Prokopiou、Derek H. R. Barton、Robin B. Boar、Laurette Joukhadar、James F. McGhie、Satish C. Misra

  DOI：10.1039/p19810001501

  日期：——

  Diverse carboxylic esters have been reduced with dissolving Group 1A metals. Using lithium in ethylamine, sterically hindered esters (RCO2R′) were deoxygenated giving the alkane (R′H) whereas non-hindered esters regenerated the parent alcohol (R′OH). This permitted the selective deoxygenation of diesters. Conversely, potassium–sodium eutectic solubilised with 18-crown-6 in t-butylamine and tetrahydrofuran

  溶解1A族金属可还原各种羧酸酯。使用乙胺中的锂，将位阻酯（RCO 2 R'）脱氧，得到烷烃（R'H），而无阻酯则再生出母体醇（R'OH）。这允许二酯的选择性脱氧。相反，用18-crown-6溶解于叔丁胺和四氢呋喃（THF）中的钾钠共晶可有效地对受阻酯和非受阻酯进行脱氧。在室温下不存在亲核试剂的情况下，羧酸酯基团阴离子的主要反应是脱氧。
• Deshayes, Henri; Pete, Jean-Pierre, Canadian Journal of Chemistry, 1984, vol. 62, p. 2063 - 2072
  作者：Deshayes, Henri、Pete, Jean-Pierre

  DOI：——

  日期：——
• Transesterification. I. β-Keto Esters
  作者：Alfred R. Bader、Lowell O. Cummings、Henry A. Vogel

  DOI：10.1021/ja01153a045

  日期：1951.9
• A convenient approach to chiral sulfoxides by enantioselective oxidation with a steroidal furylhydroperoxide
  作者：Laura Palombi、Francesco Bonadies、Alessandro Pazienza、Arrigo Scettri

  DOI：10.1016/s0957-4166(98)00163-3

  日期：1998.5

  The introduction of a steroidal residue into a position distant from the reaction center shows a beneficial effect on the reactivity of secondary furylhydroperoxides: chiral sulfoxides are obtained by asymmetric oxidation of sulfides and/or kinetic resolution of racemic sulfoxides with reduced reaction times and high enantiomeric excesses. (C) 1998 Elsevier Science Ltd. All rights reserved.