(1'S,2'S,7'S,10'S,13'R)-2',6',6',12'-tetramethylspiro[1,3-dithiolane-2,14'-tetracyclo[11.2.1.01,10.02,7]hexadec-11-ene] | 1316759-88-2

• 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: (1'S,2'S,7'S,10'S,13'R)-2',6',6',12'-tetramethylspiro[1,3-dithiolane-2,14'-tetracyclo[11.2.1.01,10.02,7]hexadec-11-ene]
• CAS: 1316759-88-2
• 化学式: C₂₂H₃₄S₂
• 分子量: 362.644
• InChiKey: BCVOQCVVGLFXRM-LBFCPWMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1'S,2'S,7'S,10'S,13'R)-2',6',6',12'-tetramethylspiro[1,3-dithiolane-2,14'-tetracyclo[11.2.1.01,10.02,7]hexadec-11-ene] 在 Raney-Ni 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以76%的产率得到(+)-stemar-13-ene
  参考文献：
  名称：

  Diastereoselective Total Synthesis of (+)-13-Stemarene by Fourth Generation Methods: A Formal Total Synthesis of (+)-18-Deoxystemarin

  摘要：

  The problem of constructing diastereoselectively the C/D ring system of stemarane diterpenes from a bicyclo[2.2.2]octane intermediate was solved resulting in very simple synthesis of (+)-13-stemarene 1. The obtaining of the latter represents also a formal synthesis of (+)-18-deoxystemarin 2. In the key step, the epimeric mixture 10, dissolved in toluene, was converted by the action of TsOH into (+)-stemar-13-en-15-one 28.

  DOI：

  10.1021/jo200945s
• 作为产物：
  描述：

  (1S,2S,7S,10S,12S)-16-hydroxy-2,6,6,12-tetramethyltetracyclo[10.2.2.01,10.02,7]hexadecan-13-one 在 三氟化硼乙醚 、 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 24.17h， 生成 (1'S,2'S,7'S,10'S,13'R)-2',6',6',12'-tetramethylspiro[1,3-dithiolane-2,14'-tetracyclo[11.2.1.01,10.02,7]hexadec-11-ene]
  参考文献：
  名称：

  Diastereoselective Total Synthesis of (+)-13-Stemarene by Fourth Generation Methods: A Formal Total Synthesis of (+)-18-Deoxystemarin

  摘要：

  The problem of constructing diastereoselectively the C/D ring system of stemarane diterpenes from a bicyclo[2.2.2]octane intermediate was solved resulting in very simple synthesis of (+)-13-stemarene 1. The obtaining of the latter represents also a formal synthesis of (+)-18-deoxystemarin 2. In the key step, the epimeric mixture 10, dissolved in toluene, was converted by the action of TsOH into (+)-stemar-13-en-15-one 28.

  DOI：

  10.1021/jo200945s