1-Methyl-r-1,c-2-cyclopropandicarbonsaeure-dimethylester | 702-91-0

• 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: 1-Methyl-r-1,c-2-cyclopropandicarbonsaeure-dimethylester
• 英文别名: cis-Dimethyl 1-methyl-1,2-cyclopropanedicarboxylate；1-Methyl-cyclopropan-cis-1,2-dicarbonsaeure-dimethylester；(+/-)-1-methyl-cyclopropane-dicarboxylic acid-(1r.2c)-dimethyl ester；(+/-)-1-Methyl-cyclopropan-dicarbonsaeure-(1r.2c)-dimethylester；1-Methyl-cyclopropan-1r,2c-dicarbonsaeure-dimethylester；dimethyl (1R,2S)-1-methylcyclopropane-1,2-dicarboxylate
• CAS: 702-91-0
• 化学式: C₈H₁₂O₄
• 分子量: 172.181
• InChiKey: NDRULFBEMISCLM-SVGQVSJJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 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：

  1-Methyl-r-1,c-2-cyclopropandicarbonsaeure-dimethylester 在 氢氧化钾 、 乙酰氯 作用下， 以 水 为溶剂， 反应 18.5h， 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：

  cis-2-Methoxycarbonyl-1-methylcyclopropanecarboxylic acid 生成 1-Methyl-r-1,c-2-cyclopropandicarbonsaeure-dimethylester
  参考文献：
  名称：

  Alkylation, Acylation, and Cyclopropanation Reactions ofa-Halo Carboxylic Acid Dianions

  摘要：

  DOI：

  10.1055/s-1982-29781

文献信息

• Synthesis and mode of action of 1-substituted trans-cyclopropane 1,2-dicarboxylic acids: inhibitors of the methylaspartase reaction
  作者：Kamal Badiani、Philip Lightfoot、David Gani

  DOI：10.1039/cc9960000675

  日期：——

  A range of 1-substituted cyclopropane 1,2-dicarboxylic acids are synthesised using short efficient routes and are found to be good to potent inhibitors of 3-methylaspartase; the crystallographically determined absolute stereochemistry and the mode of action of the most potent inhibitor, (1S,2S)-1-methylcyclopropane 1,2-dicarboxylic acid, is consistent with it acting as a transition state analogue for the central substrate deamination reaction catalysed by the enzyme.

  我们采用简捷高效的方法合成了一系列 1-取代环丙烷 1,2 二羧酸，发现它们是 3-甲基天冬氨酸酶的良好至强效抑制剂；经晶体学测定，最强效抑制剂 (1S,2S)-1- 甲基环丙烷 1,2 二羧酸的绝对立体化学结构和作用模式与它作为该酶催化的中心底物脱氨反应的过渡态类似物是一致的。
• <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。
• v.Auwers; Koenig, Justus Liebigs Annalen der Chemie, 1932, vol. 496, p. 280
  作者：v.Auwers、Koenig

  DOI：——

  日期：——
• Saal, Wolfgang von der; Reinhardt, Robert; Seidenspinner, Hubert-Matthias, Liebigs Annalen der Chemie, 1989, p. 703 - 712
  作者：Saal, Wolfgang von der、Reinhardt, Robert、Seidenspinner, Hubert-Matthias、Stawitz, Josef、Quast, Helmut

  DOI：——

  日期：——
• v.Auwers; Cauer, Justus Liebigs Annalen der Chemie, 1929, vol. 470, p. 298
  作者：v.Auwers、Cauer

  DOI：——

  日期：——