2-butyl-2-hydroxymethylcyclopentan-1-one | 128038-94-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-butyl-2-hydroxymethylcyclopentan-1-one
• 英文别名: 2-butyl-2-hydroxymethylcyclopentanone；2-hydroxymethyl-2-butylcyclopentanone；2-Butyl-2-(hydroxymethyl)cyclopentan-1-one
• CAS: 128038-94-8
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: LSPFSPJXBNPDLF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 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：

  2-butyl-2-hydroxymethylcyclopentan-1-one 在 palladium on activated charcoal 4-二甲氨基吡啶 、 氢气 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 lithium bromide 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 23.0h， 生成 7a-butyl-hexahydrocyclopenta[c]pyran-3(1H)-one
  参考文献：
  名称：

  Synthesis of pseudoiridolactones

  摘要：

  Bicyclic delta-lactones with a carbon group at the bicyclic junction C-7a, designed as pseudoiridolactones, were synthesized from alpha-alkyl-alpha-hydroxymethylcyclopentanones via an intramolecular Horner-Wadsworth-Emmons reaction. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.02.027
• 作为产物：
  描述：

  ethyl 1-butyl-(2,2-ethylenedioxy)cyclopentanecarboxylate 在 盐酸 、 lithium aluminium tetrahydride 、 水 作用下， 以 乙醚 为溶剂， 反应 3.0h， 生成 2-butyl-2-hydroxymethylcyclopentan-1-one
  参考文献：
  名称：

  Synthesis of pseudoiridolactones

  摘要：

  Bicyclic delta-lactones with a carbon group at the bicyclic junction C-7a, designed as pseudoiridolactones, were synthesized from alpha-alkyl-alpha-hydroxymethylcyclopentanones via an intramolecular Horner-Wadsworth-Emmons reaction. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.02.027

文献信息

• IBX/n-Bu4NBr/CH2Cl2–H2O: a new mild system for selective oxidation of secondary alcohols
  作者：Chutima Kuhakarn、Krisada Kittigowittana、Manat Pohmakotr、Vichai Reutrakul

  DOI：10.1016/j.tet.2005.07.051

  日期：2005.9

  A new alternative system for the chemoselective oxidation of secondary hydroxyl group to ketone with IBX/n-Bu4NBr in CH2Cl2–H2O has been developed. Under the reaction conditions, the secondary hydroxyl group was highly chemoselectively oxidized to the corresponding ketone, in moderate to good yields at rt, in the presence of primary hydroxyl group within the same molecule.

  开发了一种新的替代系统，用于在CH 2 Cl 2 -H 2 O中用IBX / n -Bu 4 NBr将仲羟基化学选择性氧化为酮。在反应条件下，在同一分子内存在伯羟基的情况下，仲羟基在室温下以中等至良好的收率被高度化学选择性氧化为相应的酮。
• 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.