(+/-)-trans-<2-Methyl-cyclopropyl>-carbonsaeureamid | 1759-49-5

• 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: (+/-)-trans-<2-Methyl-cyclopropyl>-carbonsaeureamid
• 英文别名: (+/-)-trans-2-Methyl-cyclopropan-carbonsaeure-(1)-amid；(+/-)-trans-2-Methyl-cyclopropan-carbamid；trans-2-Methyl-cyclopropancarboxamid；(1R,2R)-2-methylcyclopropane-1-carboxamide
• CAS: 1759-49-5；6142-58-1；81428-99-1；107912-92-5；107912-93-6
• 化学式: C₅H₉NO
• 分子量: 99.1326
• InChiKey: FGJUPRFXIMWVNF-QWWZWVQMSA-N

物化性质

• 熔点：
  110 °C
• 沸点：
  235.5±7.0 °C(Predicted)
• 密度：
  1.081±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  43.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (+/-)-trans-<2-Methyl-cyclopropyl>-carbonsaeureamid 在 phosphorus pentoxide 作用下， 生成 trans-1-cyano-2-methylcyclopropane
  参考文献：
  名称：

  Synthesis and absolute configurations of some optically active cis- and trans-1,2-disubstituted cyclopropanes

  摘要：

  DOI：

  10.1021/ja01054a032
• 作为产物：
  描述：

  4-氯戊酸乙酯 生成 (+/-)-trans-<2-Methyl-cyclopropyl>-carbonsaeureamid
  参考文献：
  名称：

  金属-氨溶液对乙酰环丙烷的环裂解机理

  摘要：

  金属-氨溶液还原乙酰环丙烷涉及环丙烷环的裂解。提出了该过程的机制，该机制解释了以下观察结果：（i）裂解形成饱和酮的裂解中的取代基作用表明碳负离子种类的重排;（ii）饱和酮的整体还原涉及每个分子两个电子，（iii当使用低浓度的锂时，自由基会发生还原性二聚化特征，并且（iv）某些起始酮始终保持不变。观察到由1-乙酰基-2，2-二甲基环丙烷形成的两个裂解产物的比例随锂浓度线性变化。讨论了这种效果的两种可能的解释。已经研究了2-取代的环丙基羰基自由基的优选裂解方向。的尼克-辛兹反应N-（反式-2-甲基环丙基甲基）甲苯-对-磺酰胺产物，表明中间体烷基二酰亚胺的分解遵循自由基而不是碳负离子途径。

  DOI：

  10.1039/p29740001347

文献信息

• Analogs of isovaleramide, a pharmaceutical composition including the same, and a method of treating central nervous system conditions or diseases
  申请人：Artman D. Linda

  公开号：US20060025477A1

  公开（公告）日：2006-02-02

  An isovaleramide analog having at least one of an increased potency, an increased half-life, and an increased stability compared to isovaleramide. The isovaleramide analog is a cyclic analog or a noncyclic analog. The isovaleramide analog is formulated into a pharmaceutical composition. A method of treating a central nervous system condition or disease is also disclosed. The method comprises administering an isovaleramide analog to a patient suffering from the central nervous system condition or disease.

  一种异戊酰胺类似物，相比异戊酰胺，至少具有增强的效力、延长的半衰期和增强的稳定性中的一种。该异戊酰胺类似物是环状类似物或非环状类似物。该异戊酰胺类似物被制成药物组合物。还揭示了一种治疗中枢神经系统疾病或疾病的方法。该方法包括向患有中枢神经系统疾病或疾病的患者施用异戊酰胺类似物。
• Inhibition of the mammalian .beta.-lactamase renal dipeptidase (dehydropeptidase-I) by Z-2-(acylamino)-3-substituted-propenoic acids
  作者：Donald W. Graham、Wallace T. Ashton、Louis Barash、Jeannette E. Brown、Ronald D. Brown、Laura F. Canning、Anna Chen、James P. Springer、Edward F. Rogers

  DOI：10.1021/jm00389a018

  日期：1987.6

  The title enzyme deactivates the potent carbapenem antibiotic imipenem in the kidney, producing low antibiotic levels in the urinary tract. A series of (Z)-2-(acylamino)-3-substituted-propenoic acids (3) are specific, competitive inhibitors of the enzyme capable of increasing the urinary concentration of imipenem in vivo. Many of the compounds were prepared in one step from an alpha-keto acid and a primary amide. The optimum R2 groups are 2,2-dimethyl, -dichloro, and -dibromocyclopropyl. With R2 = 2,2-dimethylcyclopropyl (DMCP), a wide variety of R3 groups including alkyl, oxa- and thiaalkyl, and alkyl groups containing acidic, basic, and neutral substituents give effective inhibitors with Ki values of 0.02-1 microM and a range of pharmacokinetic properties. By resolution of enantiomers and X-ray crystallography, the enzyme-inhibitory activity of the DMCP group was found to reside with the 1S isomer. The cysteinyl compound 176 (cilastatin, MK-0791) has the desired pharmacological properties and has been chosen for combination with imipenem.
• Synthesis and absolute configurations of some optically active cis- and trans-1,2-disubstituted cyclopropanes
  作者：Robert G. Bergman

  DOI：10.1021/ja01054a032

  日期：1969.12
• Mechanism of ring cleavage of acetylcyclopropanes by metal–ammonia solutions
  作者：Anthony J. Bellamy、Ewen A. Campbell、Ian R. Hall

  DOI：10.1039/p29740001347

  日期：——

  The reduction of acetylcyclopropanes by metal–ammonia solutions involves cleavage of the cyclopropane ring. A mechanism for this process is proposed which accounts for the observations that (i) substituent effects in the cleavage to form the saturated ketone indicate rearrangement of a carbanionic species, (ii) the overall reduction to saturated ketone involves two electrons per molecule, (iii) reductive

  金属-氨溶液还原乙酰环丙烷涉及环丙烷环的裂解。提出了该过程的机制，该机制解释了以下观察结果：（i）裂解形成饱和酮的裂解中的取代基作用表明碳负离子种类的重排;（ii）饱和酮的整体还原涉及每个分子两个电子，（iii当使用低浓度的锂时，自由基会发生还原性二聚化特征，并且（iv）某些起始酮始终保持不变。观察到由1-乙酰基-2，2-二甲基环丙烷形成的两个裂解产物的比例随锂浓度线性变化。讨论了这种效果的两种可能的解释。已经研究了2-取代的环丙基羰基自由基的优选裂解方向。的尼克-辛兹反应N-（反式-2-甲基环丙基甲基）甲苯-对-磺酰胺产物，表明中间体烷基二酰亚胺的分解遵循自由基而不是碳负离子途径。