(3S,8S,9S,10R,13S,17R)-17-[(2S,3R)-3-羟基-6-甲基庚-5-烯-2-基]-10,13-二甲基-2,3,4,7,8,9,11,12,14,15,16,17-十二氢-1H-环戊二烯并[a]菲-3-醇 | 54604-98-7

• 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
• 中文名称: (3S,8S,9S,10R,13S,17R)-17-[(2S,3R)-3-羟基-6-甲基庚-5-烯-2-基]-10,13-二甲基-2,3,4,7,8,9,11,12,14,15,16,17-十二氢-1H-环戊二烯并[a]菲-3-醇
• 英文名称: (3S,8S,9S,10R,13S,14S,17R)-17-((1S,2R)-2-Hydroxy-1,5-dimethyl-hex-4-enyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
• 英文别名: 22R-hydroxydesmosterol；(3S,8S,9S,10R,13S,14S,17R)-17-[(2S,3R)-3-hydroxy-6-methylhept-5-en-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
• CAS: 54604-98-7
• 化学式: C₂₇H₄₄O₂
• 分子量: 400.645
• InChiKey: DJZMVDQAHDXJDB-GFKLAVDKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3S,8S,9S,10R,13S,17R)-17-[(2S,3R)-3-羟基-6-甲基庚-5-烯-2-基]-10,13-二甲基-2,3,4,7,8,9,11,12,14,15,16,17-十二氢-1H-环戊二烯并[a]菲-3-醇 在 叔丁基过氧化氢 、 bis(acetylacetonate)oxovanadium 作用下， 以 二氯甲烷 为溶剂， 以91%的产率得到22(R)-Hydroxy-24(S),25-Epoxycholesterol
  参考文献：
  名称：

  Simple, stereocontrolled syntheses of 24(S),25-epoxy-22(R)-hydroxycholesterol, 22(R),24(S)-dihydroxycholesterol and diastereomers, new ligands for binding and activation of LXRs

  摘要：

  Described herein are stereocontrolled syntheses of a series of sidechain oxygenated cholesterols for the study of binding and activation of nuclear receptors of the LXR family. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02182-0
• 作为产物：
  描述：

  3β-(t-butyldimethylsilyloxy)-23,24-dinorchol-5-enaldehyde 在 TEA 、 四丁基氟化铵 、 双(三甲基硅烷基)氨基钾 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.67h， 生成 (3S,8S,9S,10R,13S,17R)-17-[(2S,3R)-3-羟基-6-甲基庚-5-烯-2-基]-10,13-二甲基-2,3,4,7,8,9,11,12,14,15,16,17-十二氢-1H-环戊二烯并[a]菲-3-醇
  参考文献：
  名称：

  Simple, stereocontrolled syntheses of 24(S),25-epoxy-22(R)-hydroxycholesterol, 22(R),24(S)-dihydroxycholesterol and diastereomers, new ligands for binding and activation of LXRs

  摘要：

  Described herein are stereocontrolled syntheses of a series of sidechain oxygenated cholesterols for the study of binding and activation of nuclear receptors of the LXR family. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)02182-0

文献信息

• Simple, stereocontrolled syntheses of 24(S),25-epoxy-22(R)-hydroxycholesterol, 22(R),24(S)-dihydroxycholesterol and diastereomers, new ligands for binding and activation of LXRs
  作者：E.J. Corey、Michael J. Grogan

  DOI：10.1016/s0040-4039(98)02182-0

  日期：1998.12

  Described herein are stereocontrolled syntheses of a series of sidechain oxygenated cholesterols for the study of binding and activation of nuclear receptors of the LXR family. (C) 1998 Elsevier Science Ltd. All rights reserved.