[(5R,6S)-5,6-dimethyl-6-[(2Z)-3-methylpenta-2,4-dienyl]cyclohexen-1-yl] trifluoromethanesulfonate | 1191092-54-2

• 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: [(5R,6S)-5,6-dimethyl-6-[(2Z)-3-methylpenta-2,4-dienyl]cyclohexen-1-yl] trifluoromethanesulfonate
• CAS: 1191092-54-2
• 化学式: C₁₅H₂₁F₃O₃S
• 分子量: 338.391
• InChiKey: NMAMOINSIGTNAM-KRFXKNSESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(5R,6S)-5,6-dimethyl-6-[(2Z)-3-methylpenta-2,4-dienyl]cyclohexen-1-yl] trifluoromethanesulfonate 、 三甲基铟 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 生成 、 striatene
  参考文献：
  名称：

  Synthesis of (+)-striatene: confirmation of its stereostructure

  摘要：

  The first enantioselective synthesis of natural striatene (+)-1, isolated from liverwort Ptychanthus striatus, starting from commercially available (R)-Pulegone is described. Its stereostructure was confirmed by X-ray analysis of a 3,5-dinitrobenzoate derivative obtained from a key intermediate and its high optical purity was verified by chiral HPLC. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.07.138
• 作为产物：
  描述：

  N-苯基双(三氟甲烷磺酰)亚胺 、 (2S,3R)-2,3-Dimethyl-2-((Z)-3-methyl-penta-2,4-dienyl)-cyclohexanone 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 13.0h， 以83%的产率得到[(5R,6S)-5,6-dimethyl-6-[(2Z)-3-methylpenta-2,4-dienyl]cyclohexen-1-yl] trifluoromethanesulfonate
  参考文献：
  名称：

  Synthesis of (+)-striatene: confirmation of its stereostructure

  摘要：

  The first enantioselective synthesis of natural striatene (+)-1, isolated from liverwort Ptychanthus striatus, starting from commercially available (R)-Pulegone is described. Its stereostructure was confirmed by X-ray analysis of a 3,5-dinitrobenzoate derivative obtained from a key intermediate and its high optical purity was verified by chiral HPLC. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.07.138

文献信息

• Synthesis of (+)-striatene: confirmation of its stereostructure
  作者：Paul Brémond、Nicolas Vanthuyne、Gérard Audran

  DOI：10.1016/j.tetlet.2009.07.138

  日期：2009.10

  The first enantioselective synthesis of natural striatene (+)-1, isolated from liverwort Ptychanthus striatus, starting from commercially available (R)-Pulegone is described. Its stereostructure was confirmed by X-ray analysis of a 3,5-dinitrobenzoate derivative obtained from a key intermediate and its high optical purity was verified by chiral HPLC. (C) 2009 Elsevier Ltd. All rights reserved.