3,3-dimethyl-1,4-dihydroxymethylcyclopentene | 239085-69-9

• 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: 3,3-dimethyl-1,4-dihydroxymethylcyclopentene
• 英文别名: [4-(Hydroxymethyl)-2,2-dimethylcyclopent-3-en-1-yl]methanol
• CAS: 239085-69-9
• 化学式: C₉H₁₆O₂
• 分子量: 156.225
• InChiKey: LPKCMDZKJQLJJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,3-dimethyl-1,4-dihydroxymethylcyclopentene 在 喹啉 、 mercury(II) diacetate 、 叔丁基硫醇 、 丙酸 作用下， 以 苯 为溶剂， 反应 8.0h， 生成 (-)-(1R,3R)-ethyl 2,3,3-trimethyl-4-methylidenecyclopentanemethanol
  参考文献：
  名称：

  Stereocontrolled total synthesis of (±)-β-necrodol

  摘要：

  A total synthesis of racemic beta-necrodol is described using an ortho-ester Claisen rearrangement as the key step to dictate a high level of trans-1,3-diastereoselection on a cyclopentane derivative. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00737-6
• 作为产物：
  描述：

  2,2-dimethyl-3-hydroxymethyl cyclopentanone 在 咪唑 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 三氟化硼乙醚 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 3,3-dimethyl-1,4-dihydroxymethylcyclopentene
  参考文献：
  名称：

  Stereocontrolled total synthesis of (±)-β-necrodol

  摘要：

  A total synthesis of racemic beta-necrodol is described using an ortho-ester Claisen rearrangement as the key step to dictate a high level of trans-1,3-diastereoselection on a cyclopentane derivative. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00737-6

文献信息

• Stereocontrolled total synthesis of (±)-β-necrodol
  作者：Susanta Samajdar、Anjan Ghatak、Subrata Ghosh

  DOI：10.1016/s0040-4039(99)00737-6

  日期：1999.6

  A total synthesis of racemic beta-necrodol is described using an ortho-ester Claisen rearrangement as the key step to dictate a high level of trans-1,3-diastereoselection on a cyclopentane derivative. (C) 1999 Elsevier Science Ltd. All rights reserved.
• High diastereoselectivity in Claisen rearrangement in a sterically congested cyclopentane system. Total synthesis of (±)-β-necrodol
  作者：Susanta Samajdar、Anjan Ghatak、Shyamapada Banerjee、Subrata Ghosh

  DOI：10.1016/s0040-4020(01)00019-9

  日期：2001.3

  Total synthesis of the monoterpene beta -necrodol has been accomplished. The key step involves an ortho-ester Claisen rearrangement in a highly sterically congested cyclopentane derivative resulting in a high level of 1,3-trans diastereoselection. A novel photo-induced decarboxylation of the obtained gamma,delta -unsaturated acid afforded beta -necrodol. (C) 2001 Elsevier Science Ltd. All rights reserved.