2-[(1S)-1-ethyl-2-oxocyclopentyl]acetic acid

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[(1S)-1-ethyl-2-oxocyclopentyl]acetic acid
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: JUJNUVSBHYIYFA-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.61
• 重原子数：
  12.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  54.37
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  2-氧代环戊羧酸烯丙酯 在 (S)-(CF₃)₃-t-BuPHOX 、 ruthenium trichloride 、 sodium periodate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 potassium carbonate 作用下， 以 水 、 丙酮 、 甲苯 、 乙腈 为溶剂， 反应 49.0h， 生成 2-[(1S)-1-ethyl-2-oxocyclopentyl]acetic acid
  参考文献：
  名称：

  Palladium-Catalyzed Enantioselective Decarboxylative Allylic Alkylation of Cyclopentanones

  摘要：

  The first general method for the enantioselective construction of all-carbon quaternary centers on cyclopentanones by enantioselective palladium-catalyzed decarboxylative allylic alkylation is described. Employing the electronically modified (S)-(p-CF3)(3)-t-BuPHOX ligand, alpha-quaternary cyclopentanones were isolated in yields up to >99% with ee's up to 94%. Additionally, in order to facilitate large-scale application of this method, a low catalyst loading protocol was employed, using as little as 0.15 mol % Pd, furnishing the product without any loss in ee.

  DOI：

  10.1021/acs.orglett.5b02376

文献信息

• Palladium-Catalyzed Enantioselective Decarboxylative Allylic Alkylation of Cyclopentanones
  作者：Robert A. Craig、Steven A. Loskot、Justin T. Mohr、Douglas C. Behenna、Andrew M. Harned、Brian M. Stoltz

  DOI：10.1021/acs.orglett.5b02376

  日期：2015.11.6

  The first general method for the enantioselective construction of all-carbon quaternary centers on cyclopentanones by enantioselective palladium-catalyzed decarboxylative allylic alkylation is described. Employing the electronically modified (S)-(p-CF3)(3)-t-BuPHOX ligand, alpha-quaternary cyclopentanones were isolated in yields up to >99% with ee's up to 94%. Additionally, in order to facilitate large-scale application of this method, a low catalyst loading protocol was employed, using as little as 0.15 mol % Pd, furnishing the product without any loss in ee.