(R)-2-hydroxymethyl-2-methylcyclopentanone

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-2-hydroxymethyl-2-methylcyclopentanone
• 英文别名: 2-(hydroxymethyl)-2-methylcyclopentanone；(2R)-2-(Hydroxymethyl)-2-methylcyclopentanone；(2R)-2-(hydroxymethyl)-2-methylcyclopentan-1-one
• 化学式: C₇H₁₂O₂
• 分子量: 128.171
• InChiKey: AUALHRBQAJTKPR-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  苯甲酰氯 、 (R)-2-hydroxymethyl-2-methylcyclopentanone 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (1-methyl-2-oxocyclopentyl)methyl benzoate
  参考文献：
  名称：

  使用具有手性钪络合物的甲醛水溶液催化硅烯醇化物的不对称羟甲基化

  摘要：

  已经实现了硅烯醇化物的催化不对称羟甲基化。在该反应中，可以使用甲醛的水溶液来实现简单且安全的过程，并且获得了较高的对映选择性。这是在水性介质中与手性钪络合物进行催化不对称反应的第一个例子。

  DOI：

  10.1021/ja047896i
• 作为产物：
  描述：

  乙酸乙烯酯 、 2-(羟甲基)-2-甲基环戊烷-1-酮 在 Pseudomonas cepacia Amano PS lipase 作用下， 以 正戊烷 为溶剂， 反应 3.0h， 以46%的产率得到(R)-2-acetoxymethyl-2-methylcyclopentanone
  参考文献：
  名称：

  Lipase-catalyzed kinetic resolution of α-hydroxymethylcycloalkanones with a quaternary carbon center. Chemoenzymatic synthesis of chiral pseudoiridolactones

  摘要：

  The resolution of alpha-alkyl-alpha-hydroxymethylcyclopentanones 1 and cyclohexanones 3 has been efficiently achieved by using lipase-catalyzed transesterification reactions with vinyl acetate as the acylating agent. The enantiomeric selectivities were dependent on both the ring size of the cycloalkanone and the bulk of the carbon group located at the stereogenic quaternary center. The resolved alpha-alkyl-alpha-hydroxymethylcyclopentanones 1 were used as enantiopure (or enantioenriched) precursors for the synthesis of the optically active pseudoiridolactones 6-7. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.04.043

文献信息

• Catalytic Asymmetric Hydroxymethylation of Silicon Enolates Using an Aqueous Solution of Formaldehyde with a Chiral Scandium Complex
  作者：Shunpei Ishikawa、Tomoaki Hamada、Kei Manabe、Shū Kobayashi

  DOI：10.1021/ja047896i

  日期：2004.10.1

  Catalytic asymmetric hydroxymethylation of silicon enolates has been achieved. In this reaction, an aqueous solution of formaldehyde can be used to realize an easy and safe procedure, and high enantioselectivities have been obtained. This is the first example of catalytic asymmetric reactions in aqueous media with a chiral scandium complex.

  已经实现了硅烯醇化物的催化不对称羟甲基化。在该反应中，可以使用甲醛的水溶液来实现简单且安全的过程，并且获得了较高的对映选择性。这是在水性介质中与手性钪络合物进行催化不对称反应的第一个例子。
• Lipase-catalyzed kinetic resolution of α-hydroxymethylcycloalkanones with a quaternary carbon center. Chemoenzymatic synthesis of chiral pseudoiridolactones
  作者：Zineb Guerrab、Stefan Schweiger、Boujemâa Daou、Mohammed Ahmar、Bernard Cazes

  DOI：10.1016/j.tetasy.2010.04.043

  日期：2010.7

  The resolution of alpha-alkyl-alpha-hydroxymethylcyclopentanones 1 and cyclohexanones 3 has been efficiently achieved by using lipase-catalyzed transesterification reactions with vinyl acetate as the acylating agent. The enantiomeric selectivities were dependent on both the ring size of the cycloalkanone and the bulk of the carbon group located at the stereogenic quaternary center. The resolved alpha-alkyl-alpha-hydroxymethylcyclopentanones 1 were used as enantiopure (or enantioenriched) precursors for the synthesis of the optically active pseudoiridolactones 6-7. (C) 2010 Elsevier Ltd. All rights reserved.