α-Isopropyl-acetessigsaeure-tert.-butylester | 92057-99-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: α-Isopropyl-acetessigsaeure-tert.-butylester
• 英文别名: 2-Isopropyl-acetessigsaeure-tert.-butylester；Isopropyl-acetessigsaeure-tert.-butylester
• CAS: 92057-99-3
• 化学式: C₁₁H₂₀O₃
• 分子量: 200.278
• InChiKey: GMQIEPMXIOWDHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.19
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  α-Isopropyl-acetessigsaeure-tert.-butylester 反应 12.0h， 生成 3,4-dimethyl-2-pentanone
  参考文献：
  名称：

  Coppens,W.; Schamp,N., Bulletin des Societes Chimiques Belges, 1972, vol. 81, p. 643 - 648

  摘要：

  DOI：
• 作为产物：
  描述：

  乙酰乙酸叔丁酯 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 0.17h， 生成 α-Isopropyl-acetessigsaeure-tert.-butylester
  参考文献：
  名称：

  Catalytic Enantioselective Carbon Insertion into the β-Vinyl C–H Bond of Cyclic Enones

  摘要：

  Chiral oxazaborolidinium ion-catalyzed C-sp(2)-H functionalization of enones using diazoacetate has been developed. Various beta-substituted cyclic enones were synthesized in high yield (up to 99%) with high to excellent enantioselectivity (up to 99% ee). The synthetic utility of this reaction was demonstrated by the formal synthesis of (+)-epijuvabione.

  DOI：

  10.1021/ja402873b

文献信息

• Highly enantioselective catalytic 1,3-dipolar cycloadditions of α-alkyl diazoacetates: efficient synthesis of functionalized 2-pyrazolines
  作者：Sung Il Lee、Ka Eun Kim、Geum-Sook Hwang、Do Hyun Ryu

  DOI：10.1039/c4ob02372b

  日期：——

  Highly enantioselective 1,3-dipolar cycloaddition reactions of α-substituted diazoacetates are accomplished by catalysis of the chiral oxazaborolidinium ion. Functionalized 2-pyrazolines are synthesized in high to excellent enantiomeric ratios (up to >99 : 1). The synthetic utility of 2-pyrazoline was expanded via preparation of 2,4-diamino ester compounds bearing a chiral quaternary carbon center.

  α-取代的重氮乙酸酯的高度对映选择性的1，3-偶极环加成反应通过手性恶唑硼烷鎓离子的催化来完成。功能化的2-吡唑啉以高至极好的对映体比例（高达> 99：1）合成。通过制备带有手性季碳中心的2，4-二氨基酯化合物，扩大了2-吡唑啉的合成用途。
• Lawesson,S.-O. et al., Acta Chemica Scandinavica (1947), 1962, vol. 16, p. 1191 - 1198
  作者：Lawesson,S.-O. et al.

  DOI：——

  日期：——
• Lawesson,S.-O. et al., Recueil des Travaux Chimiques des Pays-Bas, 1964, vol. 83, p. 464 - 468
  作者：Lawesson,S.-O. et al.

  DOI：——

  日期：——
• Catalytic Carbon Insertion into the β-Vinyl C–H Bond of Cyclic Enones with Alkyl Diazoacetates
  作者：Sung Il Lee、Byung Chul Kang、Geum-Sook Hwang、Do Hyun Ryu

  DOI：10.1021/ol4000026

  日期：2013.4.5

  The first example of the boron Lewis acid catalyzed C-SP2-H functionalization of cyclic enones was achieved using diazoacetates. The insertion of the carbon atom of diazoacetates utilizes BF3 center dot Et2O or a newly designed oxazaborolidinium ion as a catalyst to afford beta-functionalized cyclic enones from simple cyclic enones In a single step and high yields. The reaction mechanism was investigated with deuterium labeled 2-cyclohexen-1-one.
• A Simple and Efficient Preparation of Propargylic β-Keto Esters through Transesterification
  作者：Christophe Mottet、Olivier Hamelin、Geraldine Garavel、Jean-Pierre Deprés、Andrew E. Greene

  DOI：10.1021/jo9818172

  日期：1999.2.1