1-pentylcyclopropene-3-carboxylic acid | 95411-46-4

• 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
• 英文名称: 1-pentylcyclopropene-3-carboxylic acid
• 英文别名: 1-pentylcyclopropene-3-carboxylic acid methyl ester；propyl 1-methylcyclopropene-3-carboxylate；methyl ester of 1-amylcyclopropenecarboxylic acid；methyl 1-pentylcyclopropene-3-carboxylate；methyl 2-pentylcycloprop-2-ene-1-carboxylate
• CAS: 95411-46-4
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: BJOPTQWSYJPEHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-pentylcyclopropene-3-carboxylic acid 在 potassium diazodicarboxylate 、 溶剂黄146 作用下， 以35%的产率得到(1R,2S)-methyl cis-2-n-pentylcyclopropane-1-carboxylate
  参考文献：
  名称：

  Effective Uses of Dirhodium(II) Tetrakis[methyl 2-oxopyrrolidine-5(R or S)-carboxylate] for Highly Enantioselective Intermolecular Cyclopropenation Reactions

  摘要：

  The title compounds are effective catalysts for intermolecular cyclopropenation reactions of l-alkynes with diazo esters and diazo amides. Diastereoselectivities achieved from the appropriate match with d- or l-menthyl diazoacetate are 77 to greater than or equal to 94% de. Enantioselectivities up to greater than or equal to 94% ee with 3-methoxy-1-propyne and 3,3-diethoxy-1 -propyne have been obtained. Variations in these values for metal carbene additions to alkynes are associated with electronic and/or steric influences from the alkyne or carbene substituents. N,N-Dimethyldiazoacetamide provides a higher level of enantiocontrol than do diazo esters. The absolute configurations of the cyclopropene products have been established; dirhodium(II) tetrakis[methyl 2-oxopyrrolidine-5(S)-carboxylate], Rh-2(5S-MEPY)(4), produces 2-substituted-2-cyclopropene-1-carboxylates having the (S)-configuration whereas use of Rh-2(5R-MEPY)(4) provides these cyclopropene products in the (R)-configuration. Diimide reduction of these cyclopropenecarboxylates produces the cis-disubstituted cyclopropane products exclusively.

  DOI：

  10.1021/ja00098a009

文献信息

• Regioselective catalytic addition of proton-donor reagents to esters of 1-alkylcyclopropene-3-carboxylic acids
  作者：E. A. Shapiro、M. N. Protopopova、O. M. Nefedov

  DOI：10.1007/bf01455477

  日期：1988.4
• Selective catalytic addition of hydrogen halide and carboxylic acids and phenols to methyl esters of 1-alkyl-3-cyclopropenecarboxylic acids
  作者：E. A. Shapiro、M. N. Protopopova、O. M. Nefedov

  DOI：10.1007/bf00948662

  日期：1984.9
• Regioselective catalyzed addition of proton-donor reagents to 1-alkylcyclopropene-3-carboxylate esters. 3. Reaction of methyl cyclopropane-3-carboxylates with compounds containing labile hydrogen at oxygen, sulfur, or nitrogen
  作者：E. A. Shapiro、M. N. Protopopova、O. M. Nefedov

  DOI：10.1007/bf00953416

  日期：1988.10
• Vinylcyclopropanation of norbornadiene, norbornene, and dispiroheptadiene by methyl esters of 1-alkylcyclopropene-3-carboxylic acids
  作者：M. N. Protopopova、E. A. Shapiro、O. M. Nefedov

  DOI：10.1007/bf00963033

  日期：1990.1
• Regioselective catalytic addition of terminal acetylenes to methyl esters of 1-alkylcyclopropene-3-carboxylic acids
  作者：M. N. Protopopova、E. A. Shapiro、Yu. V. Tomilov、I. E. Dolgii、O. M. Nefedov

  DOI：10.1007/bf00963270

  日期：1985.10