反式-1-甲基-1,2-环丙烷二羧酸 | 697-49-4

• 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
• 中文名称: 反式-1-甲基-1,2-环丙烷二羧酸
• 英文名称: trans-1-methyl-1,2-cyclopropanedicarboxylic acid
• 英文别名: trans 1-methylcyclopropane 1,2-diacid；(+/-)-1-methyl-cyclopropane-1r,2t-dicarboxylic acid；(+/-)-1-Methyl-cyclopropan-1r,2t-dicarbonsaeure；(+/-)-1-Methyl-cyclopropan-dicarbonsaeure-(1r.2t)；1-Methyl-cyclopropan-1r,2t-dicarbonsaeure；(1R,2R)-1-methylcyclopropane-1,2-dicarboxylic acid
• CAS: 697-49-4
• 化学式: C₆H₈O₄
• 分子量: 144.127
• InChiKey: CUXGZYHWQYTLKE-BBIVZNJYSA-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：

  反式-1-甲基-1,2-环丙烷二羧酸 在 乙酸酐 作用下， 生成 1-甲基-3-氧杂双环[3.1.0]己烷-2,4-二酮
  参考文献：
  名称：

  Mousseron et al., Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1959, vol. 248, p. 1465

  摘要：

  DOI：
• 作为产物：
  描述：

  2-O-ethyl 1-O-methyl 1-methylcyclopropane-1,2-dicarboxylate 在 sodium hydroxide 作用下， 反应 15.0h， 生成 反式-1-甲基-1,2-环丙烷二羧酸
  参考文献：
  名称：

  Palladium(II) Acetate, an Efficient Catalyst for Cyclopropanation Reactions with Ethyl Diazoacetate

  摘要：

  DOI：

  10.1055/s-1983-30385

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。
• 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。
• Novel heterocyclic amide derivatives and their use as dopamine D3 receptor ligands
  申请人：Hendrix A. James

  公开号：US20050107389A1

  公开（公告）日：2005-05-19

  The invention relates to heterocyclic substituted amide derivatives that display selective binding to dopamine D 3 receptors. In another aspect, the invention relates to a method for treating central nervous system disorders associated with the dopamine D 3 receptor activity in a patient in need of such treatment comprising administering to the subject a therapeutically effective amount of said compounds for alleviation of such disorder. The central nervous system disorders that may be treated with these compounds include Psychotic Disorders, Substance Dependence, Substance Abuse, Dyskinetic Disorders (e.g. Parkinson's Disease, Parkinsonism, Neuroleptic-Induced Tardive Dyskinesia, Gilles de la Tourette Syndrome and Huntington's Disease), Dementia, Anxiety Disorders, Sleep Disorders, Circadian Rhythm Disorders and Mood Disorders. The subject invention is also directed towards processes for the preparation of the compounds described herein as well as methods for making and using the compounds as imaging agents for dopamine D 3 receptors.

  本发明涉及杂环取代酰胺衍生物，其表现出对多巴胺D3受体的选择性结合。在另一个方面，本发明涉及一种治疗中枢神经系统疾病的方法，该疾病与多巴胺D3受体活性有关，包括精神病性障碍、物质依赖、物质滥用、运动障碍（例如帕金森病、帕金森综合症、神经阻滞剂引起的迟发性运动障碍、吉尔·德·拉·图雷特综合症和亨廷顿病）、痴呆、焦虑症、睡眠障碍、昼夜节律紊乱和情绪障碍。本发明还涉及制备上述化合物的过程，以及将这些化合物作为多巴胺D3受体成像剂的方法。
• Novel Heterocyclic Substituted Carbonyl Derivatives and Their Use as Dopamine D3 Receptor Ligands
  申请人：Hendrix James A.

  公开号：US20090247509A1

  公开（公告）日：2009-10-01

  The invention relates to heterocyclic substituted carbonyl derivatives that display selective binding to dopamine D 3 receptors. In another aspect, the invention relates to a method for treating central nervous system disorders associated with the dopamine D 3 receptor activity in a patient in need of such treatment comprising administering to the subject a therapeutically effective amount of said compounds for alleviation of such disorder. The central nervous system disorders that may be treated with these compounds include Psychotic Disorders, Substance Dependence, Substance Abuse, Dyskinetic Disorders (e.g. Parkinson's Disease, Parkinsonism, Neuroleptic-Induced Tardive Dyskinesia, Gilles de la Tourette Syndrome and Huntington's Disease), Dementia, Anxiety Disorders, Sleep Disorders, Circadian Rhythm Disorders and Mood Disorders. The subject invention is also directed towards processes for the preparation of the compounds described herein as well as methods for making and using the compounds as imaging agents for dopamine D 3 receptors.

  本发明涉及杂环取代羰基衍生物，其表现出对多巴胺D3受体的选择性结合。另一方面，本发明涉及一种治疗与多巴胺D3受体活性相关的中枢神经系统疾病的方法，该方法包括向需要此类治疗的患者施用所述化合物的治疗有效量，以缓解此类疾病。这些化合物可以治疗的中枢神经系统疾病包括精神疾病、物质依赖、物质滥用、运动障碍（例如帕金森病、帕金森综合症、神经阻滞引起的迟发性运动障碍、吉尔斯-德-拉-图雷综合症和亨廷顿病）、痴呆、焦虑症、睡眠障碍、昼夜节律紊乱和情绪障碍。本发明还涉及制备所述化合物的方法以及将所述化合物作为多巴胺D3受体成像剂的制备和使用方法。