2-[[(1S,3S)-1-methyl-2-methylidene-3-propan-2-ylcyclopentyl]methyl]-1,3-dioxolane | 616205-97-1

• 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: 2-[[(1S,3S)-1-methyl-2-methylidene-3-propan-2-ylcyclopentyl]methyl]-1,3-dioxolane
• CAS: 616205-97-1
• 化学式: C₁₄H₂₄O₂
• 分子量: 224.343
• InChiKey: JERYHYVSDLRDQA-JSGCOSHPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[[(1S,3S)-1-methyl-2-methylidene-3-propan-2-ylcyclopentyl]methyl]-1,3-dioxolane 在 盐酸 、 sodium tetrahydroborate 、 水 、 叔丁基锂 、 臭氧 、 三氯氧磷 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 正己烷 为溶剂， 反应 34.0h， 生成 (S)-trifluoromethanesulfonic acid 2-[2-(3-isopropyl-1-methylcyclopent-2-enyl)acetyl]-3-methoxy-5-methylphenyl 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
• 作为产物：
  描述：

  1,2-双(三甲基硅氧基)乙烷 、 (-)-(2S,5S)-5-isopropyl-2-methyl-2-(2-oxoethyl)methylenecyclopentane 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到2-[[(1S,3S)-1-methyl-2-methylidene-3-propan-2-ylcyclopentyl]methyl]-1,3-dioxolane
  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

文献信息

• Enantiospecific total synthesis of 6-epi-(−)-hamigeran B. Intramolecular Heck reaction in a sterically constrained environment
  作者：Goverdhan Mehta、Harish M. Shinde

  DOI：10.1016/s0040-4039(03)01754-4

  日期：2003.9

  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.