24-methylenecholest-4-ene-3,6-dione | 59048-87-2

• 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-ene-3,6-dione
• 英文别名: 24-methylenecholest-4-en-3,6-dione；(8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-2,7,8,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthrene-3,6-dione
• CAS: 59048-87-2
• 化学式: C₂₈H₄₂O₂
• 分子量: 410.64
• InChiKey: AFPIZEGCVWFIIW-DQQDKUJHSA-N

物化性质

• 熔点：
  122-124 °C
• 沸点：
  512.7±20.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  24-methylenecholest-4-ene-3,6-dione 在 sodium tetrahydroborate 、 cerium(III) chloride 作用下， 以 甲醇 为溶剂， 反应 0.25h， 以89%的产率得到24-methylenecholest-4-en-3β,6α-diol
  参考文献：
  名称：

  Synthesis of polyhydroxysterols (III): synthesis and structural elucidation of 24-methylenecholest-4-en-3β,6α-diol

  摘要：

  Using stigmasterol as the starting material, 24-methylenecholest-4-en-3beta,6alpha-diol (2) was synthesized in eight steps in 13% overall yield. The introduction of the sterol side-chain was carried out using (3-methyl-2-oxobutyl)-triphenylarsonium bromide (11) and K2CO3 in a solid-liquid phase-transfer Wittig reaction. Construction of the steroidal nucleus was finished by oxidation of 24-methylenecholest-5-en-3beta-ol (9) with pyridinium chlorochromate (PCC) in dichloromethane at ambient temperature and by reduction of 24-methylenecholest-4-en-3,6-dione (10) with NaBH4 in the presence of CeCl3.7H(2)O. (C) 2002 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(02)00059-4
• 作为产物：
  描述：

  豆甾醇 在 platinum(IV) oxide 盐酸 、 iodobenzene dibromide 、 氢气 、 sodium hydride 、 potassium carbonate 、 臭氧 、 formamide 、 二甲基亚砜 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 乙酸乙酯 、 乙腈 为溶剂， 反应 85.5h， 生成 24-methylenecholest-4-ene-3,6-dione
  参考文献：
  名称：

  Synthesis of polyhydroxysterols (III): synthesis and structural elucidation of 24-methylenecholest-4-en-3β,6α-diol

  摘要：

  Using stigmasterol as the starting material, 24-methylenecholest-4-en-3beta,6alpha-diol (2) was synthesized in eight steps in 13% overall yield. The introduction of the sterol side-chain was carried out using (3-methyl-2-oxobutyl)-triphenylarsonium bromide (11) and K2CO3 in a solid-liquid phase-transfer Wittig reaction. Construction of the steroidal nucleus was finished by oxidation of 24-methylenecholest-5-en-3beta-ol (9) with pyridinium chlorochromate (PCC) in dichloromethane at ambient temperature and by reduction of 24-methylenecholest-4-en-3,6-dione (10) with NaBH4 in the presence of CeCl3.7H(2)O. (C) 2002 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(02)00059-4

文献信息

• Synthesis of polyhydroxysterols (III): synthesis and structural elucidation of 24-methylenecholest-4-en-3β,6α-diol
  作者：Jian Guo Cui、Cui Wu Lin、Long Mei Zeng、Jing Yu Su

  DOI：10.1016/s0039-128x(02)00059-4

  日期：2002.12

  Using stigmasterol as the starting material, 24-methylenecholest-4-en-3beta,6alpha-diol (2) was synthesized in eight steps in 13% overall yield. The introduction of the sterol side-chain was carried out using (3-methyl-2-oxobutyl)-triphenylarsonium bromide (11) and K2CO3 in a solid-liquid phase-transfer Wittig reaction. Construction of the steroidal nucleus was finished by oxidation of 24-methylenecholest-5-en-3beta-ol (9) with pyridinium chlorochromate (PCC) in dichloromethane at ambient temperature and by reduction of 24-methylenecholest-4-en-3,6-dione (10) with NaBH4 in the presence of CeCl3.7H(2)O. (C) 2002 Elsevier Science Inc. All rights reserved.