cis 1-methylcyclopropane 1,2-diacid | 697-48-3

• 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: cis 1-methylcyclopropane 1,2-diacid
• 英文别名: cis-1-Methyl-1,2-cyclopropanedicarboxylic acid；cis (±)-1-methylcyclopropane-1,2-dicarboxylic acid；1-Methyl-cis-1.2-dicarboxy-cyclopropan；(+/-)-1-methyl-cyclopropane-1r,2c-dicarboxylic acid；(+/-)-1-Methyl-cyclopropan-dicarbonsaeure-(1r.2c)；(+/-)-1-Methyl-cyclopropan-1r,2c-dicarbonsaeure；(1R,2S)-1-methylcyclopropane-1,2-dicarboxylic acid
• CAS: 697-48-3
• 化学式: C₆H₈O₄
• 分子量: 144.127
• InChiKey: CUXGZYHWQYTLKE-AWFVSMACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  cis 1-methylcyclopropane 1,2-diacid 在 乙酰氯 作用下， 反应 4.5h， 生成 cis-2-Methoxycarbonyl-1-methylcyclopropanecarboxylic acid
  参考文献：
  名称：

  Synthesis of racemic cis-1-alkyl- and 1-aryl-2-aminocyclopropanecarboxylic esters

  摘要：

  The title cyclic beta-amino esters were synthesized stereo- and regioselectively. Starting from the corresponding 1-aryl- and 1-alkylcyclopropane-1,2-dicarboxylates, selective monosaponification and subsequent Curtius reaction leads to certain cis-1-alkyl-and 1-aryl-2-aminocyclopropanecarboxylic esters. These P-aminocyclopropanecarboxylate derivatives (beta-ACCs) can be seen as useful building blocks for beta-peptides. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00126-6
• 作为产物：
  描述：

  2-氯丙酸乙酯 在 sodium ethanolate 作用下， 生成 cis 1-methylcyclopropane 1,2-diacid
  参考文献：
  名称：

  The presumed synthesis of 1,3-cyclobutane-dicarboxylic acid by Markownikoff and Krestownikoff

  摘要：

  DOI：

  10.1007/bf02154104

文献信息

• Metal hydride reductions of unsymmetrically substituted cyclic anhydrides attached to strained ring systems
  作者：Margaret M. Kayser、Judith Salvador、Peter Morand、H. G. Krishnamurty

  DOI：10.1139/v82-178

  日期：1982.5.15

  reversal in regioselectivity is observed in the metal hydride reduction of unsymmetrical cyclic anhydrides such as 2,3, and 4 compared to cyclic anhydrides attached to bridged ring systems (e.g. 1). The synthesis of model cyclic anhydrides attached to strained rings is described and the ratios of isomeric lactones obtained upon reduction with metal hydride are reported. On the basis of theoretical calculations

  与连接到桥环系统（例如 1）的环状酸酐相比，在不对称环状酸酐（例如 2,3 和 4）的金属氢化物还原中观察到区域选择性的显着逆转。描述了连接到应变环的模型环酐的合成，并报告了用金属氢化物还原后获得的异构内酯的比率。在理论计算的基础上，并考虑到羰基的固有反应性、反周向效应和空间拥挤，对在这些化合物的还原中观察到的区域选择性进行了解释。
• Highly Enantioselective Intermolecular Cyclopropanation Catalyzed by Dirhodium(II) Tetrakis[3(<i>S</i>)-phthalimido-2-piperidinonate]: Solvent Dependency of the Enantioselection
  作者：Shinji Kitagaki、Hideo Matsuda、Nobuhide Watanabe、Shun-ichi Hashimoto

  DOI：10.1055/s-1997-994

  日期：1997.10

  The enantioselectivity in cyclopropanations catalyzed by dirhodium(II) tetrakis[3(S)-phthalimido-2-piperidinonate] has been found to be substantially improved by employing ether as the rarely used solvent. Cyclopropanations of styrenes or 1,1-disubstituted alkenes with 2,4-dimethyl-3-pentyl diazoacetate in ether are promoted by this catalyst to afford the corresponding cyclopropane products in the highest levels of enantioselectivity (up to 98% ee) reported to date for the dirhodium(II)-catalyzed intermolecular cyclopropanation reactions.

  由二铑(II)四[3(S)-邻苯二甲酰胺-2-哌啶酸酯]催化的环丙烷化反应中的对映选择性已被发现通过使用作为罕见溶剂的醚显著改善。该催化剂促进了苯乙烯或1,1-二取代烯烃与2,4-二甲基-3-戊基二氮酰乙酸酯在醚中进行的环丙烷化反应，产生了相应的环丙烷产品，报告的对映选择性达到最高水平（高达98% ee），这是迄今为止二铑(II)催化的分子间环丙烷化反应中所取得的最高记录。
• <b>Nuclear Magnetic Resonance Spectroscopy. Cyclopropane Derivatives</b>
  作者：Dinshaw J. Patel、M. E. H. Howden、John D. Roberts

  DOI：10.1021/ja00903a036

  日期：1963.10

  constants have been determined from the analysis of proton nuclear magnetic resonance spectra for a series of cyclopropane derivatives. The geminal and vicinal cyclopropyl couplings have opposite signs. Additional ^(13)C-H coupling constants have been obtained for cyclopropanes which support the conclusion that the hybridization of the carbon-hydrogen bonding orbitals in cyclopropanes is close to sp. The chemical

  通过对一系列环丙烷衍生物的质子核磁共振谱的分析，已经确定了化学位移和耦合常数。孪生和邻位环丙基偶联具有相反的符号。已经获得了环丙烷的额外 ^(13)CH 偶联常数，这支持了环丙烷中碳氢键轨道的杂化接近 sp 的结论。几种环丙烷烃的化学位移似乎与环流效应一致。
• Design, synthesis and activity of novel derivatives of Oxybutynin and Tolterodine
  作者：Kirandeep Kaur、Shelly Aeron、Miriyala Bruhaspathy、Shankar J. Shetty、Suman Gupta、Laxminarayan H. Hegde、Arun D.V. Silamkoti、Anita Mehta、Anita Chugh、Jang B. Gupta、P.K.S. Sarma、Naresh Kumar

  DOI：10.1016/j.bmcl.2005.02.036

  日期：2005.4

  Novel derivatives of Tolterodine (1) and Oxybutynin (2) have been designed using conformationally restricted azabicyclics as replacement for open-chain amines. The synthesis and structure-activity relationships are presented. (c) 2005 Elsevier Ltd. All rights reserved.
• Alkylation, Acylation, and Cyclopropanation Reactions of<i>a</i>-Halo Carboxylic Acid Dianions
  作者：Carl R. Johnson、Thomas R. Bade

  DOI：10.1055/s-1982-29781

  日期：——