cyclopentanemethanol, 2,2-dimethyl-5-methylene | 177087-98-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: cyclopentanemethanol, 2,2-dimethyl-5-methylene
• 英文别名: (+/-)-2,2-dimethyl-5-methylidene-cyclopentane methanol；(2,2-Dimethyl-5-methylenecyclopentyl)methanol；(2,2-dimethyl-5-methylidenecyclopentyl)methanol
• CAS: 177087-98-8
• 化学式: C₉H₁₆O
• 分子量: 140.225
• InChiKey: IIRWHTHSAWDLJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  cyclopentanemethanol, 2,2-dimethyl-5-methylene 在 乙酸乙烯酯 、 Amano AK lipase 作用下， 反应 7.0h， 以37%的产率得到(-)-(1S)-2,2-dimethyl-5-methylidene-cyclopentane methanol
  参考文献：
  名称：

  Lipase-mediated kinetic resolution of allylic(hydroxymethyl)methylenecyclopentane building blocks

  摘要：

  Enzymatic-mediated kinetic acylation of allylic(hydroxymethyl)methylenecyclopentane building blocks (+/-)-1a,b is reported using various commercially available lipases, Lipase Amano AK (Pseudomonas sp.) proved to be the best lipase in the case of (-)-1b which was obtained with a 96% enantiomeric excess. Single crystal X-ray diffraction analysis, using the (1S,4R)-camphanate derivative of (-)-1b, helped us to assign the S absolute configuration of (-)-1b and the enantiomeric specificity of the tested lipases. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00082-3
• 作为产物：
  描述：

  聚合甲醛 、 (3,3-环乙烷-1-ENYLMETHYL)三甲基硅烷 在 二甲基氯化铝 、 四氯化锡 作用下， 生成 cyclopentanemethanol, 2,2-dimethyl-5-methylene
  参考文献：
  名称：

  Isocyclic Allylsilanes: An Efficient One-Pot Synthesis of Allylic Hydroxymethyl Methylenecycloalkane Building Blocks by a Controlled H-ene/Protodesilylation Sequence Using Two Different Lewis Acids

  摘要：

  An efficient one-pot synthesis of useful allylic hydroxymethyl methylenecycloalkane building blocks was achieved by a controlled H-ene / protodesilylation sequence using two different Lewis acids (Me(2)AlCl / SnCl4) and starting from readily available isocyclic allylsilanes.

  DOI：

  10.1080/00397919608002611

文献信息

• Lipase-mediated kinetic resolution of allylic(hydroxymethyl)methylenecyclopentane building blocks
  作者：Gilles Laval、Guiliana Cardillo、Honoré Monti、Alessandra Tolomelli、Gérard Audran、Jean-Marie Galano

  DOI：10.1016/s0957-4166(00)00082-3

  日期：2000.4

  Enzymatic-mediated kinetic acylation of allylic(hydroxymethyl)methylenecyclopentane building blocks (+/-)-1a,b is reported using various commercially available lipases, Lipase Amano AK (Pseudomonas sp.) proved to be the best lipase in the case of (-)-1b which was obtained with a 96% enantiomeric excess. Single crystal X-ray diffraction analysis, using the (1S,4R)-camphanate derivative of (-)-1b, helped us to assign the S absolute configuration of (-)-1b and the enantiomeric specificity of the tested lipases. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Isocyclic Allylsilanes: An Efficient One-Pot Synthesis of Allylic Hydroxymethyl Methylenecycloalkane Building Blocks by a Controlled H-ene/Protodesilylation Sequence Using Two Different Lewis Acids
  作者：Honoré Monti、Michel Féraud

  DOI：10.1080/00397919608002611

  日期：1996.5

  An efficient one-pot synthesis of useful allylic hydroxymethyl methylenecycloalkane building blocks was achieved by a controlled H-ene / protodesilylation sequence using two different Lewis acids (Me(2)AlCl / SnCl4) and starting from readily available isocyclic allylsilanes.