methyl trans-2-formylcyclohexanecarboxylate

• 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: methyl trans-2-formylcyclohexanecarboxylate
• 英文别名: methyl trans-2-formylcyclohexane-1-carboxylate；Methyl-trans-2-formylcyclohexan-1-carboxylat；methyl (1S,2S)-2-formylcyclohexane-1-carboxylate
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: DGHWGHPZRYEZDI-SFYZADRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl trans-2-formylcyclohexanecarboxylate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 2.0h， 生成 benzhydryl (1R,2R)-2-(1-hydroxy-2-methylprop-2-enyl)cyclohexane-1-carboxylate
  参考文献：
  名称：

  Angiotensin-converting enzyme inhibitors: importance of the amide carbonyl of mercaptoacyl amino acids for hydrogen bonding to the enzyme

  摘要：

  A series of mercaptoacyl amino acids and related compounds was synthesized and evaluated for inhibition of angiotensin-converting enzyme (ACE) in order to determine the nature and importance of the putative interaction between ACE and the amide moiety of inhibitors such as captopril (3-mercapto-2-methylpropanoyl-L-proline). It was concluded that the interaction involves a hydrogen bond from a donor site on ACE to the oxygen of the amide carbonyl. Compounds in which the amide moiety is replaced by other groups (ester, ketone, sulfonamide) capable of accepting a hydrogen bond are effective inhibitors, but compounds in which only the geometrical features of the amide are retained are ineffective inhibitors. The presence of an NH group is not necessary for effective inhibition. The activity of a series of mercaptoacyl cycloalkyl carboxylic acids parallels the activity of the isosteric series of mercaptoacyl imino acids.

  DOI：

  10.1021/jm00345a011
• 作为产物：
  描述：

  trans-2-(methoxycarbonyl)cyclohexanecarboxylic acid 在 碳酸氢钠 、 戴斯-马丁氧化剂 、 三乙胺 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 methyl trans-2-formylcyclohexanecarboxylate
  参考文献：
  名称：

  Synthesis of trans-fused Octahydroisoindole-1-carboxylic Acids

  摘要：

  反式-融合八氢异吲哚-1-羧酸是一种双环脯氨酸类似物，在寻找新药方面具有潜在的意义。在这项工作中，我们使用反式-2-（羟甲基）环己烷-1-羧酸甲酯作为关键合成前体，构建了反式融合八氢异吲哚体系，而反式-2-（羟甲基）环己烷-1-羧酸甲酯又很容易从廉价的顺式-环己烷-1,2-二羧酸酐中制备出来。 (1S*,3aR*,7aR*)-和(1R*,3aR*,7aR*)-八氢异吲哚-1-羧酸都是通过反式-2-甲酰基环己烷-1-羧酸甲酯的 Strecker 反应作为关键步骤制备的。最后，以(3aR*,7aR*)-八氢异吲哚-1-酮为合适的支架，以高度立体选择性的方式获得了(1S*,3aR*,7aR*)-八氢异吲哚-1-羧酸。

  DOI：

  10.2174/1570178614666171130161203

文献信息

• Yagoub,A.K. et al., Journal of the Chemical Society. Perkin transactions I, 1977, p. 697 - 699
  作者：Yagoub,A.K. et al.

  DOI：——

  日期：——
• Angiotensin-converting enzyme inhibitors: importance of the amide carbonyl of mercaptoacyl amino acids for hydrogen bonding to the enzyme
  作者：Michael E. Condon、Edward W. Petrillo、Denis E. Ryono、Joyce A. Reid、Richard Neubeck、Mohindar Puar、James E. Heikes、Emily F. Sabo、Kathryn A. Losee

  DOI：10.1021/jm00345a011

  日期：1982.3

  A series of mercaptoacyl amino acids and related compounds was synthesized and evaluated for inhibition of angiotensin-converting enzyme (ACE) in order to determine the nature and importance of the putative interaction between ACE and the amide moiety of inhibitors such as captopril (3-mercapto-2-methylpropanoyl-L-proline). It was concluded that the interaction involves a hydrogen bond from a donor site on ACE to the oxygen of the amide carbonyl. Compounds in which the amide moiety is replaced by other groups (ester, ketone, sulfonamide) capable of accepting a hydrogen bond are effective inhibitors, but compounds in which only the geometrical features of the amide are retained are ineffective inhibitors. The presence of an NH group is not necessary for effective inhibition. The activity of a series of mercaptoacyl cycloalkyl carboxylic acids parallels the activity of the isosteric series of mercaptoacyl imino acids.
• Synthesis of trans-fused Octahydroisoindole-1-carboxylic Acids
  作者：Pedro Laborda、Francisco J. Sayago、Carlos Cativiela、Vicente Gotor

  DOI：10.2174/1570178614666171130161203

  日期：2018.4.12

  trans-Fused octahydroisoindole-1-carboxylic acids are bicyclic proline analogues of potential interest in the search for new drugs. Within this work, the trans-fused octahydroisoindole system has been constructed using methyl trans-2-(hydroxymethyl)cyclohexane-1-carboxylate as the key synthetic precursor, in turn readily prepared from inexpensive cis-cyclohexane-1,2-dicarboxylic anhydride. Both the (1S*,3aR*,7aR*)- and the (1R*,3aR*,7aR*)-octahydroisoindole-1-carboxylic acids were prepared through the Strecker reaction of methyl trans-2-formylcyclohexane-1-carboxylate as the key step. Finally, (1S*,3aR*,7aR*)-octahydroisoindole-1-carboxylic acid was obtained with good yields in a highly stereoselective manner using (3aR*,7aR*)-octahydroisoindole-1-one as a suitable scaffold.

  反式-融合八氢异吲哚-1-羧酸是一种双环脯氨酸类似物，在寻找新药方面具有潜在的意义。在这项工作中，我们使用反式-2-（羟甲基）环己烷-1-羧酸甲酯作为关键合成前体，构建了反式融合八氢异吲哚体系，而反式-2-（羟甲基）环己烷-1-羧酸甲酯又很容易从廉价的顺式-环己烷-1,2-二羧酸酐中制备出来。 (1S*,3aR*,7aR*)-和(1R*,3aR*,7aR*)-八氢异吲哚-1-羧酸都是通过反式-2-甲酰基环己烷-1-羧酸甲酯的 Strecker 反应作为关键步骤制备的。最后，以(3aR*,7aR*)-八氢异吲哚-1-酮为合适的支架，以高度立体选择性的方式获得了(1S*,3aR*,7aR*)-八氢异吲哚-1-羧酸。