Trifluoro-methanesulfonic acid 1-[2-((S)-3-isopropyl-1-methyl-cyclopent-2-enyl)-acetyl]-naphthalen-2-yl ester | 616206-06-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: Trifluoro-methanesulfonic acid 1-[2-((S)-3-isopropyl-1-methyl-cyclopent-2-enyl)-acetyl]-naphthalen-2-yl ester
• 英文别名: [1-[2-[(1S)-1-methyl-3-propan-2-ylcyclopent-2-en-1-yl]acetyl]naphthalen-2-yl] trifluoromethanesulfonate
• CAS: 616206-06-5
• 化学式: C₂₂H₂₃F₃O₄S
• 分子量: 440.483
• InChiKey: MQBHDQIDWHFWIM-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  68.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Trifluoro-methanesulfonic acid 1-[2-((S)-3-isopropyl-1-methyl-cyclopent-2-enyl)-acetyl]-naphthalen-2-yl ester 在 palladium diacetate 、 1,3-双(二苯基膦)丙烷 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 2-((S)-3-Isopropyl-1-methyl-cyclopent-2-enyl)-1-naphthalen-1-yl-ethanone 、 (13S,14S)-15-Isopropylidene-13-methyl-12,13,14,15,16,17-hexahydro-cyclopenta[a]phenanthren-11-one
  参考文献：
  名称：

  Enantiospecific total synthesis of 6-epi-(−)-hamigeran B. Intramolecular Heck reaction in a sterically constrained environment

  摘要：

  An enantiospecific approach, emanating from the abundantly available chiron R-(+)-limonene, to the biologically potent, novel marine natural products, the hamigerans has been developed in which an intramolecular Heck coupling between aryl triflates and an alkene serves as the pivotal step. Following this strategy, a synthesis of (-)-6-epi-hamigeran B has been accomplished. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01754-4
• 作为产物：
  描述：

  2-[(1S)-1-methyl-3-propan-2-ylcyclopent-2-en-1-yl]acetaldehyde 在 盐酸 、 正丁基锂 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 26.5h， 生成 Trifluoro-methanesulfonic acid 1-[2-((S)-3-isopropyl-1-methyl-cyclopent-2-enyl)-acetyl]-naphthalen-2-yl ester
  参考文献：
  名称：

  Enantiospecific total synthesis of 6-epi-(−)-hamigeran B. Intramolecular Heck reaction in a sterically constrained environment

  摘要：

  An enantiospecific approach, emanating from the abundantly available chiron R-(+)-limonene, to the biologically potent, novel marine natural products, the hamigerans has been developed in which an intramolecular Heck coupling between aryl triflates and an alkene serves as the pivotal step. Following this strategy, a synthesis of (-)-6-epi-hamigeran B has been accomplished. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01754-4