(R)-2-[(3S,8S,9S,10R,13S,14S,17R)-10,13-Dimethyl-3-(tetrahydro-pyran-2-yloxy)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methyl-hept-5-enoic acid methyl ester | 104651-74-3

• 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: (R)-2-[(3S,8S,9S,10R,13S,14S,17R)-10,13-Dimethyl-3-(tetrahydro-pyran-2-yloxy)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methyl-hept-5-enoic acid methyl ester
• CAS: 104651-74-3
• 化学式: C₃₃H₅₂O₄
• 分子量: 512.773
• InChiKey: WKUJVPOPEDIJDW-JNIDGROZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.01
• 重原子数：
  37.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (R)-2-[(3S,8S,9S,10R,13S,14S,17R)-10,13-Dimethyl-3-(tetrahydro-pyran-2-yloxy)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methyl-hept-5-enoic acid methyl ester 在 碘 、 lithium methanethiolate 、 碳酸氢钠 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 potassium iodide 作用下， 以 苯 为溶剂， 反应 20.5h， 生成 (R)-3-[(3S,8S,9S,10R,13S,14S,17R)-10,13-Dimethyl-3-(tetrahydro-pyran-2-yloxy)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-isopropylidene-tetrahydro-pyran-2-one
  参考文献：
  名称：

  24(R), 25-Dihydroxycholesterol; An Attempt for Side-Chain Stereocontrol Via Iodolactonization

  摘要：

  AbstractStereocontrolled formation of the side‐chain of 24(R), 25‐dihydroxycholesterol (1) via an iodolactonization process, involving a C‐10 carboxylic function and a 24, 25 double bond, has been studied. Low stereoselectivity was observed.

  DOI：

  10.1002/bscb.19860950410
• 作为产物：
  描述：

  5-溴-2-甲基-2-戊烯 、 [(3S,8S,9S,10R,13R,14S,17R)-10,13-Dimethyl-3-(tetrahydro-pyran-2-yloxy)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-acetic acid methyl ester 在 lithium cyclohexylisopropylamide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 反应 2.0h， 以65%的产率得到(R)-2-[(3S,8S,9S,10R,13S,14S,17R)-10,13-Dimethyl-3-(tetrahydro-pyran-2-yloxy)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methyl-hept-5-enoic acid methyl ester
  参考文献：
  名称：

  24(R), 25-Dihydroxycholesterol; An Attempt for Side-Chain Stereocontrol Via Iodolactonization

  摘要：

  AbstractStereocontrolled formation of the side‐chain of 24(R), 25‐dihydroxycholesterol (1) via an iodolactonization process, involving a C‐10 carboxylic function and a 24, 25 double bond, has been studied. Low stereoselectivity was observed.

  DOI：

  10.1002/bscb.19860950410