(+/-)-neolemnanyl acetate | 80322-51-6

• 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: (+/-)-neolemnanyl acetate
• 英文别名: [(1S,3S,8S,9Z,10aS)-8-acetyloxy-1,9,10a-trimethyl-7-oxo-1,2,3,5,6,8-hexahydrobenzo[8]annulen-3-yl] acetate
• CAS: 80322-51-6；107242-60-4
• 化学式: C₁₉H₂₆O₅
• 分子量: 334.412
• InChiKey: DSAQEKCHLYCMIR-OBOQMHEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+/-)-neolemnanyl acetate 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以59%的产率得到(1R^*,3R^*,8R^*,10aS^*)-1,2,3,5,8,10a-Hexahydro-3-(acetyloxy)-8-hydroxy-1,9,10a-trimethylbenzocycloocten-7(6H)-one
  参考文献：
  名称：

  Intramolecular additions of allylsilanes to conjugated dienones. Direct stereoselective syntheses of (.+-.)-neolemnanyl acetate and (.+-.)-neolemnane

  摘要：

  The total synthesis of the marine sesquiterpenes neolemnanyl acetate (1) and neolemnane (2) is reported. An intramolecular allylsilane addition to a conjugated dienone is used to assemble the basic 6,8-fused skeleton. Functionalization of the cyclooctane ring was achieved by means of a regiospecific photooxygenation.

  DOI：

  10.1021/jo00012a036
• 作为产物：
  描述：

  (1R*,3R*,8R*,9R*,10aS*)-8,9-Epoxy-1,2,3,5,8,9,10,10a-octahydro-3-hydroxy-1,9,10a-trimethylbenzocycloocten-7(6H)-one 在 吡啶 、 4-二甲氨基吡啶 、 silver trifluoroacetate 、 四氯化钛 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 26.08h， 生成 (+/-)-neolemnanyl acetate
  参考文献：
  名称：

  Intramolecular additions of allylsilanes to conjugated dienones. Direct stereoselective syntheses of (.+-.)-neolemnanyl acetate and (.+-.)-neolemnane

  摘要：

  The total synthesis of the marine sesquiterpenes neolemnanyl acetate (1) and neolemnane (2) is reported. An intramolecular allylsilane addition to a conjugated dienone is used to assemble the basic 6,8-fused skeleton. Functionalization of the cyclooctane ring was achieved by means of a regiospecific photooxygenation.

  DOI：

  10.1021/jo00012a036

文献信息

• A direct synthesis of (±)-neolemnanyl acetates
  作者：George Majetich、Derric Lowery、Vikram Khetani

  DOI：10.1016/s0040-4039(00)94331-4

  日期：1990.1
• Neolemnane and eremophilane sesquiterpenoids from the pacific soft coral lemnalia africana
  作者：Richard R. Izac、William Fenical、Bruce Tagle、Jon Clardy

  DOI：10.1016/s0040-4020(01)98958-6

  日期：1981.1
• Intramolecular additions of allylsilanes to conjugated dienones. Direct stereoselective syntheses of (.+-.)-neolemnanyl acetate and (.+-.)-neolemnane
  作者：George Majetich、Derric Lowery、Vikram Khetani、Jee Seop Song、Kenneth Hull、Clay Ringold

  DOI：10.1021/jo00012a036

  日期：1991.6

  The total synthesis of the marine sesquiterpenes neolemnanyl acetate (1) and neolemnane (2) is reported. An intramolecular allylsilane addition to a conjugated dienone is used to assemble the basic 6,8-fused skeleton. Functionalization of the cyclooctane ring was achieved by means of a regiospecific photooxygenation.