24-methylenecholest-4-en-3β,6β-diol

• 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-methylenecholest-4-en-3β,6β-diol
• 英文别名: 24-methylenecholest-4-ene-3β,6β-diol；24-Methylenecholest-4-ene-3beta,6beta-diol；(3S,6R,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-2,3,6,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,6-diol
• 化学式: C₂₈H₄₆O₂
• 分子量: 414.672
• InChiKey: HTLJJZSYTBKDHR-JOCBKWKSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 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：

  豆甾醇 在 platinum(IV) oxide 高氯酸 、 碘苯 、 氢气 、 溴 、 氧气 、 sodium hydride 、 potassium carbonate 、 臭氧 、 calcium carbonate 、 N-溴代乙酰胺 作用下， 以 1,4-二氧六环 、 吡啶 、 甲醇 、 正己烷 、 二氯甲烷 、 N,N-二甲基乙酰胺 、 水 、 二甲基亚砜 、 乙酸乙酯 、 乙腈 为溶剂， 反应 109.5h， 生成 24-methylenecholest-4-en-3β,6β-diol
  参考文献：
  名称：

  Synthesis of polyhydroxysterols (I): synthesis of 24-methylenecholest-4-en-3β,6β-diol, a cytotoxic natural hydroxylated sterol

  摘要：

  Starting from stigmasterol (2), 24-methylenecholest-4-en-3 beta ,6 beta -diol (1), a cytotoxic natural dihydroxylated sterol, was synthesized via 10 steps in 20% overall yield. The introduction of a side-chain of sterol was achieved by solid-liquid phase-transfer Wittig reaction using (3-methyl-2-oxo)butyltriphenylarsonium bromide (12) and K2CO3. Construction of the steroidal nucleus was finished by the addition of 3 beta -acetoxycholest-5,6-en-24-one (7) with NBA in dioxane under ambient temperature and by the elimination of 3 beta, 6 beta -diacetoxy-5a-bromocholestane-24-one (9). The spectral data of the synthetic product (1) are completely consistent with those of the natural compound (1). (C) 2001 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(00)00132-x

文献信息

• Synthesis of polyhydroxysterols (I): synthesis of 24-methylenecholest-4-en-3β,6β-diol, a cytotoxic natural hydroxylated sterol
  作者：JianGuo Cui、LongMei Zeng、JingYu Su、WeiGang Lu

  DOI：10.1016/s0039-128x(00)00132-x

  日期：2001.1

  Starting from stigmasterol (2), 24-methylenecholest-4-en-3 beta ,6 beta -diol (1), a cytotoxic natural dihydroxylated sterol, was synthesized via 10 steps in 20% overall yield. The introduction of a side-chain of sterol was achieved by solid-liquid phase-transfer Wittig reaction using (3-methyl-2-oxo)butyltriphenylarsonium bromide (12) and K2CO3. Construction of the steroidal nucleus was finished by the addition of 3 beta -acetoxycholest-5,6-en-24-one (7) with NBA in dioxane under ambient temperature and by the elimination of 3 beta, 6 beta -diacetoxy-5a-bromocholestane-24-one (9). The spectral data of the synthetic product (1) are completely consistent with those of the natural compound (1). (C) 2001 Elsevier Science Inc. All rights reserved.