(-)-(2R)-2-methylcyclopropane-1,1-dicarboxylic acid dimethyl ester | 141977-78-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (-)-(2R)-2-methylcyclopropane-1,1-dicarboxylic acid dimethyl ester
• 英文别名: (R)-2-methyl-cyclopropane-1,1-dicarboxylic acid dimethyl ester；dimethyl (2R)-2-methylcyclopropane-1,1-dicarboxylate
• CAS: 141977-78-8
• 化学式: C₈H₁₂O₄
• 分子量: 172.181
• InChiKey: ZVMMUSUTUJIKID-RXMQYKEDSA-N

物化性质

• 沸点：
  172.7±13.0 °C(Predicted)
• 密度：
  1.172±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (-)-(2R)-2-methylcyclopropane-1,1-dicarboxylic acid dimethyl ester 在 盐酸 、 sodium hydroxide 、 氯化亚砜 、 sodium azide 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 (-)-(1R,2R)-norcoronamic acid
  参考文献：
  名称：

  Enantiospecific synthesis of norcoronamic acids

  摘要：

  The synthesis of enantiomerically pure norcoronamic acids, starting from enantiomerically pure 1,2-propanediols, is described. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00245-6
• 作为产物：
  描述：

  dimethyl 2-methyl-1,1-cyclopropanedicarboxylate 生成 (-)-(2R)-2-methylcyclopropane-1,1-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  An Enantioselective Chemoenzymatic Synthesis of the Four 1-Amino 2-Methylcyclopropane Carboxylic Acids

  摘要：

  DOI：

  10.1080/00397919208021100

文献信息

• Total Synthesis of (+)-Frondosin A. Application of the Ru-Catalyzed [5+2] Cycloaddition
  作者：Barry M. Trost、Yimin Hu、Daniel B. Horne

  DOI：10.1021/ja073272b

  日期：2007.9.1

  The first total synthesis of (+)-frondosin A was accomplished in 19 longest linear and 21 total steps from commercially available materials. The key features of the synthesis include a Ru-catalyzed [5+2] cycloaddition, a Claisen rearrangement, and a ring expansion to construct the core of the frondosin A in a diastereoselective and regioselective fashion. This is the first application of a Ru-catalyzed [5+2] cycloaddition in the total synthesis of a natural product. Through this synthesis, the absolute configuration of (+)-frondosin A was established.
• Enantioselective, Facially Selective Carbomagnesation of Cyclopropenes
  作者：Xiaozhong Liu、Joseph M. Fox

  DOI：10.1021/ja058101q

  日期：2006.5.1

  Described is the facially selective and enantioselective addition of carbon nucleophiles to prochiral 3-hydroxymethylcyclopropenes. The process creates up to four stereocenters in a tandem addition/capture sequence that combines three simple materials to give complex and diverse products. The asymmetry is induced by the inexpensive and recoverable ligand (S)-N-methylprolinol. The enantioselectivity (90-98% ee with MeMgCl) is high for a range of cyclopropenes and electrophiles. Importantly, the diastereoselectivity is complementary to that obtained by enantioselective cyclopropanation with aryldiazoacetates. High enantioselectivities are obtained only when methoxide is included in the reaction. Evidence is provided that at least two chiral ligands are involved in the enantioselectivity-determining step.
• BALDWIN, J. E.;ADLINGTON, R. M.;RAWLINGS, B. J., TETRAHEDRON LETT., 1985, 26, N 4, 481-484
  作者：BALDWIN, J. E.、ADLINGTON, R. M.、RAWLINGS, B. J.

  DOI：——

  日期：——
• Enantiospecific synthesis of norcoronamic acids
  作者：Alain Hercouet、Nicolas Godbert、Maurice Le Corre

  DOI：10.1016/s0957-4166(98)00245-6

  日期：1998.7

  The synthesis of enantiomerically pure norcoronamic acids, starting from enantiomerically pure 1,2-propanediols, is described. (C) 1998 Elsevier Science Ltd. All rights reserved.
• An Enantioselective Chemoenzymatic Synthesis of the Four 1-Amino 2-Methylcyclopropane Carboxylic Acids
  作者：F. Rusconi di Lugano、J. Monteiro、C. Fliche、J. Braun、F. Le Goffic

  DOI：10.1080/00397919208021100

  日期：1992.4