(2E,6E,10E,14E)-5-(benzenesulfonyl)-3,7,11,15,19-pentamethylicosa-2,6,10,14,18-pentaenyl phenyl sulfide | 1011506-17-4

• 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: (2E,6E,10E,14E)-5-(benzenesulfonyl)-3,7,11,15,19-pentamethylicosa-2,6,10,14,18-pentaenyl phenyl sulfide
• 英文别名: [(2E,6E,10E,14E)-5-(benzenesulfonyl)-3,7,11,15,19-pentamethylicosa-2,6,10,14,18-pentaenyl]sulfanylbenzene
• CAS: 1011506-17-4
• 化学式: C₃₇H₅₀O₂S₂
• 分子量: 590.935
• InChiKey: OINNQJLCLMQZSD-DHHAJINESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.9
• 重原子数：
  41
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  67.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2E,6E,10E,14E)-5-(benzenesulfonyl)-3,7,11,15,19-pentamethylicosa-2,6,10,14,18-pentaenyl phenyl sulfide 在 LiNbMoO₆ 、 双氧水 作用下， 以 甲醇 、 苯 为溶剂， 反应 11.0h， 以75%的产率得到(2E,6E,10E,14E)-1,5-bis(benzenesulfonyl)-3,7,11,15,19-pentamethylicosa-2,6,10,14,18-pentaene
  参考文献：
  名称：

  General Preparation and Controlled Cyclization of Acyclic Terpenoids

  摘要：

  [GRAPHICS]A general preparation method of the all-(E)-polyprenols 12 has been developed from readily available geranyl sulfone by the chain-extension process utilizing the C-5 unit 5 and the chain-temination process utilizing the C5 unit 10 together with the chemoselective reductive desulfortylation. The polyprenols 12 were converted to compounds 3 containing two consecutive prenyl sulfone moieties at the tail end, which underwent the controlled electrophilic cyclization only at the carbon-carbon double bonds that were remote from the flat and rigid benzenesulfonyl groups.

  DOI：

  10.1021/jo702303a
• 作为产物：
  描述：

  [(2E,6E,10E,14E)-3,7,11,15,19-pentamethylicosa-2,6,10,14,18-pentaenyl]sulfonylbenzene 、 4-溴-3-甲基-2-丁烯基苯基硫化物 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 以85%的产率得到(2E,6E,10E,14E)-5-(benzenesulfonyl)-3,7,11,15,19-pentamethylicosa-2,6,10,14,18-pentaenyl phenyl sulfide
  参考文献：
  名称：

  General Preparation and Controlled Cyclization of Acyclic Terpenoids

  摘要：

  [GRAPHICS]A general preparation method of the all-(E)-polyprenols 12 has been developed from readily available geranyl sulfone by the chain-extension process utilizing the C-5 unit 5 and the chain-temination process utilizing the C5 unit 10 together with the chemoselective reductive desulfortylation. The polyprenols 12 were converted to compounds 3 containing two consecutive prenyl sulfone moieties at the tail end, which underwent the controlled electrophilic cyclization only at the carbon-carbon double bonds that were remote from the flat and rigid benzenesulfonyl groups.

  DOI：

  10.1021/jo702303a

文献信息

• General Preparation and Controlled Cyclization of Acyclic Terpenoids
  作者：Jinchul Kuk、Beom Soo Kim、Heejung Jung、Seyoung Choi、Jung-Youl Park、Sangho Koo

  DOI：10.1021/jo702303a

  日期：2008.3.1

  [GRAPHICS]A general preparation method of the all-(E)-polyprenols 12 has been developed from readily available geranyl sulfone by the chain-extension process utilizing the C-5 unit 5 and the chain-temination process utilizing the C5 unit 10 together with the chemoselective reductive desulfortylation. The polyprenols 12 were converted to compounds 3 containing two consecutive prenyl sulfone moieties at the tail end, which underwent the controlled electrophilic cyclization only at the carbon-carbon double bonds that were remote from the flat and rigid benzenesulfonyl groups.