24-methylene-cholest-5-ene-3β,7α-diol | 99081-79-5

• 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: 24-methylene-cholest-5-ene-3β,7α-diol
• 英文别名: 3β,7α-dihydroxyergosta-5,24(28)-diene；(3S,7S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol
• CAS: 99081-79-5；99081-81-9
• 化学式: C₂₈H₄₆O₂
• 分子量: 414.672
• InChiKey: OIBDKISTMGYAJC-JEPZXVLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  24-methylene cholesteryl acetate 在 aluminum oxide 、 3 A molecular sieve 、 L-Selectride 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 24.75h， 生成 24-methylene-cholest-5-ene-3β,7α-diol
  参考文献：
  名称：

  Synthesis of polyhydroxysterols (V): efficient and stereospecific synthesis of 24-methylene-cholest-5-ene-3β,7α-diol and its C-7 epimer

  摘要：

  This paper describes the efficient and stereospecific synthesis of cytotoxicdihydroxylated sterols, 24-methylene-cholest-5-ene-3beta,7alpha-diol 1, and its C-7 epimer, 24-methylene-cholest-5-ene-3beta,7beta-diol 2. The crux of the synthesis is that the selective allylic oxidation of 24-methylenecholesteryl acetate proceeds to 24-niethylene-7-keto-cholesteryl acetate without extensive by product formation from reaction at the Delta24(28) double bond. This methodology may be useful for the preparation of other oxysterols with non-standard side chains. (C) 2004 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2004.09.010

文献信息

• Synthesis of polyhydroxysterols (V): efficient and stereospecific synthesis of 24-methylene-cholest-5-ene-3β,7α-diol and its C-7 epimer
  作者：Weigang Lu、Cuixian Zhang、Longmei Zeng、Jingyu Su

  DOI：10.1016/j.steroids.2004.09.010

  日期：2004.12

  This paper describes the efficient and stereospecific synthesis of cytotoxicdihydroxylated sterols, 24-methylene-cholest-5-ene-3beta,7alpha-diol 1, and its C-7 epimer, 24-methylene-cholest-5-ene-3beta,7beta-diol 2. The crux of the synthesis is that the selective allylic oxidation of 24-methylenecholesteryl acetate proceeds to 24-niethylene-7-keto-cholesteryl acetate without extensive by product formation from reaction at the Delta24(28) double bond. This methodology may be useful for the preparation of other oxysterols with non-standard side chains. (C) 2004 Elsevier Inc. All rights reserved.