4',8'-dimethyl-3'(E),7'-nonadienyl 5,9,13-trimethyl-1(Z),4(E),8(E),12-tetradecatraienyl sulfide | 133795-26-3

• 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: 4',8'-dimethyl-3'(E),7'-nonadienyl 5,9,13-trimethyl-1(Z),4(E),8(E),12-tetradecatraienyl sulfide
• 英文别名: (1Z,4E,8E)-1-[(3E)-4,8-dimethylnona-3,7-dienyl]sulfanyl-5,9,13-trimethyltetradeca-1,4,8,12-tetraene
• CAS: 133795-26-3
• 化学式: C₂₈H₄₆S
• 分子量: 414.739
• InChiKey: GWQUMOKWXCEJEV-KXCHOCMDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.13
• 重原子数：
  29.0
• 可旋转键数：
  15.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  4',8'-dimethyl-3'(E),7'-nonadienyl 5,9,13-trimethyl-1(Z),4(E),8(E),12-tetradecatraienyl sulfide 在 六甲基磷酰三胺 、 copper bromide dimethyl sulfide complex 、 Lithium-tri-methoxy-alanat 作用下， 以 四氢呋喃 为溶剂， 以93%的产率得到((E)-4,8-Dimethyl-nona-3,7-dienyl)-methyl-((1Z,4E,8E)-5,9,13-trimethyl-tetradeca-1,4,8,12-tetraenyl)-sulfonium; perchlorate
  参考文献：
  名称：

  Squalene synthetase inhibitors: synthesis of sulfonium ion mimics of the carbocationic intermediates

  摘要：

  Synthesis of sulfonium ion mimics 15 and 16 of the carbocationic intermediates 3 and 7, respectively, presumed to be involved in the squalene synthetase catalyzed rearrangement of farnesyl pyrophosphate (1), is reported. Synthesis of 15 involved combination of homogeranyl sulfide with with ethyl alpha-bromoacetate through use of the thallium salt or via the combination of the copper enolate of ethyl acetate and homogeranyl thiosulfonate. Alkylation of the resulting thioester with farnesyl bromide followed by reduction of the ester moiety provided the required alcohol. The sulfur was methylated with iodomethane in a solution of CH3CN and THF to yield 15. Dialkylation of acetylene with farnesyl bromide and homogeranyl thiosulfonate followed by reduction of the triple bond gave vinyl sulfides, which were methylated with iodomethane in the presence of silver perchlorate to give 16.

  DOI：

  10.1021/jo00012a016
• 作为产物：
  描述：

  homogeranyl bromide 在 六甲基磷酰三胺 、 正丁基锂 、 copper(I) bromide dimethylsulfide complex 、 Lithium-tri-methoxy-alanat 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 56.25h， 生成 4',8'-dimethyl-3'(E),7'-nonadienyl 5,9,13-trimethyl-1(Z),4(E),8(E),12-tetradecatraienyl sulfide
  参考文献：
  名称：

  Squalene synthetase inhibitors: synthesis of sulfonium ion mimics of the carbocationic intermediates

  摘要：

  Synthesis of sulfonium ion mimics 15 and 16 of the carbocationic intermediates 3 and 7, respectively, presumed to be involved in the squalene synthetase catalyzed rearrangement of farnesyl pyrophosphate (1), is reported. Synthesis of 15 involved combination of homogeranyl sulfide with with ethyl alpha-bromoacetate through use of the thallium salt or via the combination of the copper enolate of ethyl acetate and homogeranyl thiosulfonate. Alkylation of the resulting thioester with farnesyl bromide followed by reduction of the ester moiety provided the required alcohol. The sulfur was methylated with iodomethane in a solution of CH3CN and THF to yield 15. Dialkylation of acetylene with farnesyl bromide and homogeranyl thiosulfonate followed by reduction of the triple bond gave vinyl sulfides, which were methylated with iodomethane in the presence of silver perchlorate to give 16.

  DOI：

  10.1021/jo00012a016

文献信息

• OEHLSCHLAGER, ALLAN C.;SINGH, SHANKAR M.;SHARMA, SUNAINA, J. ORG. CHEM., 56,(1991) N2, C. 3856-3861
  作者：OEHLSCHLAGER, ALLAN C.、SINGH, SHANKAR M.、SHARMA, SUNAINA

  DOI：——

  日期：——
• Squalene synthetase inhibitors: synthesis of sulfonium ion mimics of the carbocationic intermediates
  作者：Allan C. Oehlschlager、Shankar M. Singh、Sunaina Sharma

  DOI：10.1021/jo00012a016

  日期：1991.6

  Synthesis of sulfonium ion mimics 15 and 16 of the carbocationic intermediates 3 and 7, respectively, presumed to be involved in the squalene synthetase catalyzed rearrangement of farnesyl pyrophosphate (1), is reported. Synthesis of 15 involved combination of homogeranyl sulfide with with ethyl alpha-bromoacetate through use of the thallium salt or via the combination of the copper enolate of ethyl acetate and homogeranyl thiosulfonate. Alkylation of the resulting thioester with farnesyl bromide followed by reduction of the ester moiety provided the required alcohol. The sulfur was methylated with iodomethane in a solution of CH3CN and THF to yield 15. Dialkylation of acetylene with farnesyl bromide and homogeranyl thiosulfonate followed by reduction of the triple bond gave vinyl sulfides, which were methylated with iodomethane in the presence of silver perchlorate to give 16.