[(1R,3aR,7aR)-1-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-1,2,3,3a,6,7-hexahydroinden-4-yl] trifluoromethanesulfonate | 166318-82-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: [(1R,3aR,7aR)-1-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-1,2,3,3a,6,7-hexahydroinden-4-yl] trifluoromethanesulfonate
• CAS: 166318-82-7
• 化学式: C₂₀H₃₁F₃O₃S
• 分子量: 408.526
• InChiKey: PWADPXDEAIDOBZ-IBOOZMTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.05
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  [(1R,3aR,7aR)-1-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-1,2,3,3a,6,7-hexahydroinden-4-yl] trifluoromethanesulfonate 在 四(三苯基膦)钯 、 lithium chloride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.0h， 生成 (1R,3aR,5aS,11aR,11bS,13aR)-13a-Methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-2,3,3a,5,5a,11a,11b,12,13,13a-decahydro-1H-indeno[5,4-a]anthracene-6,11-dione
  参考文献：
  名称：

  Synthesis and cytotoxic activity of steroid-anthraquinone hybrids

  摘要：

  Synthesis of cytotoxic steroidal derivatives containing a quinone moiety is described. The synthetic strategy is based on an unsual A + CD --> ABCD Diels-Alder approach which generates 9 beta-H cholestane analogs. The adducts formed are efficiently aromatized in basic media to give steroid-anthaquinones hybrids showing interesting cytotoxic activity on four tumor cell lines. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00693-5
• 作为产物：
  描述：

  (3S,5Z,7Ξ)-9,10-seco-8ξ-ergosta-5,10(19),22t-triene-3,7,8-triol 在 lead(IV) acetate 、 sodium hexamethyldisilazane 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 生成 [(1R,3aR,7aR)-1-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-1,2,3,3a,6,7-hexahydroinden-4-yl] trifluoromethanesulfonate
  参考文献：
  名称：

  Synthesis and cytotoxic activity of steroid-anthraquinone hybrids

  摘要：

  Synthesis of cytotoxic steroidal derivatives containing a quinone moiety is described. The synthetic strategy is based on an unsual A + CD --> ABCD Diels-Alder approach which generates 9 beta-H cholestane analogs. The adducts formed are efficiently aromatized in basic media to give steroid-anthaquinones hybrids showing interesting cytotoxic activity on four tumor cell lines. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00693-5

文献信息

• Synthesis of (17R)-17-methylincisterol, a highly degraded marine steroid
  作者：Francesco De Riccardis、Aldo Spinella、Irene Izzo、Assunta Giordano、Guido Sodano

  DOI：10.1016/0040-4039(95)00745-x

  日期：1995.6

  The synthesis of (17R)-17-methylincisterol, a highly degraded marine steroid, has been achieved starting from vitamin D-2 in 8 steps and in 13% overall yield. Its O-demethyl analog, which is an intermediate in the synthetic sequence, is possibly the true naturally occurring molecule.