4-(羟基甲基)-3,3-二甲基-1-环戊烯-1-甲醛 | 239085-68-8

• 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
• 中文名称: 4-(羟基甲基)-3,3-二甲基-1-环戊烯-1-甲醛
• 英文名称: 3,3-dimethyl-4-hydroxymethylcyclopent-1-ene-carboxaldehyde
• 英文别名: 4-(Hydroxymethyl)-3,3-dimethylcyclopentene-1-carbaldehyde
• CAS: 239085-68-8
• 化学式: C₉H₁₄O₂
• mdl: MFCD18806815
• 分子量: 154.209
• InChiKey: SYVWEPCJLHFTQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(羟基甲基)-3,3-二甲基-1-环戊烯-1-甲醛 在 sodium tetrahydroborate 、 mercury(II) diacetate 、 丙酸 作用下， 以 甲醇 为溶剂， 反应 7.0h， 生成 ((1R,3S)-3-Hydroxymethyl-2,2-dimethyl-5-methylene-cyclopentyl)-acetic acid
  参考文献：
  名称：

  High diastereoselectivity in Claisen rearrangement in a sterically congested cyclopentane system. Total synthesis of (±)-β-necrodol

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(01)00019-9
• 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 4-(羟基甲基)-3,3-二甲基-1-环戊烯-1-甲醛
  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.