5α,6β-dibromostigmast-22-en-3β-(2-tetrahydropyranyl)ether | 497841-91-5

• 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: 5α,6β-dibromostigmast-22-en-3β-(2-tetrahydropyranyl)ether
• CAS: 497841-91-5
• 化学式: C₃₄H₅₆Br₂O₂
• 分子量: 656.625
• InChiKey: HGQFSPZVEVWTEC-NJMPNAIBSA-N

物化性质

• 沸点：
  611.5±55.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  10.32
• 重原子数：
  38.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  5α,6β-dibromostigmast-22-en-3β-(2-tetrahydropyranyl)ether 在 platinum(IV) oxide 氢气 、 sodium hydride 、 potassium carbonate 、 臭氧 、 formamide 、 二甲基亚砜 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 反应 13.5h， 生成 5,24(28)-胆甾二烯-24-亚甲基-3beta-醇
  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 盐酸 、 iodobenzene dibromide 作用下， 反应 24.0h， 生成 5α,6β-dibromostigmast-22-en-3β-(2-tetrahydropyranyl)ether
  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