(-)-8-phenylmenthyl α-pyridiniumacetate | 791576-05-1

• 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: (-)-8-phenylmenthyl α-pyridiniumacetate
• 英文别名: [(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] 2-pyridin-1-ium-1-ylacetate
• CAS: 791576-05-1
• 化学式: C₂₃H₃₀NO₂
• 分子量: 352.497
• InChiKey: IALFLXKIAGFSKC-HMXCVIKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-pyridinylmethylenepropanedinitrile 、 (-)-8-phenylmenthyl α-pyridiniumacetate 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 l-8-phenylmenthyl (1R,3S)-2,2-dicyano-3-(4-pyridyl)cyclopropanecarboxylate 、 l-8-phenylmenthyl (1S,3R)-2,2-dicyano-3-(4-pyridyl)cyclopropanecarboxylate
  参考文献：
  名称：

  Stereoselective formation of activated cyclopropanes with pyridinium ylides bearing a (−)-8-phenylmenthyl group as the chiral auxiliary

  摘要：

  The reaction of various mono-substituted methylidenemalononitriles with (-)-8-phenylmenthyl alpha -pyridiniumacetate in the presence of base afforded the corresponding dicyanocyclopropane compounds with exclusive trans-selectivity and good diastereoselectivity (up to 86.14). The stereochemistry of the major products were determined to be of 1R configuration by X-ray structural analysis of the crystalline tuans -2,2-dicyano-3-(4-pyridyl)cyclopropanecarboxylate. The geometric and diastereofacial selectivities were rationalized assuming anti-periplanar approach in the open-chain model, followed by epimerization and then cyclization to give the cyclopropane compounds. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01743-3
• 作为产物：
  描述：

  吡啶 、 (1R,2S,5R)-(+)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl chloroacetate 生成 (-)-8-phenylmenthyl α-pyridiniumacetate
  参考文献：
  名称：

  Stereoselective formation of activated cyclopropanes with pyridinium ylides bearing a (−)-8-phenylmenthyl group as the chiral auxiliary

  摘要：

  The reaction of various mono-substituted methylidenemalononitriles with (-)-8-phenylmenthyl alpha -pyridiniumacetate in the presence of base afforded the corresponding dicyanocyclopropane compounds with exclusive trans-selectivity and good diastereoselectivity (up to 86.14). The stereochemistry of the major products were determined to be of 1R configuration by X-ray structural analysis of the crystalline tuans -2,2-dicyano-3-(4-pyridyl)cyclopropanecarboxylate. The geometric and diastereofacial selectivities were rationalized assuming anti-periplanar approach in the open-chain model, followed by epimerization and then cyclization to give the cyclopropane compounds. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01743-3

文献信息

• Stereoselective formation of activated cyclopropanes with pyridinium ylides bearing a (−)-8-phenylmenthyl group as the chiral auxiliary
  作者：Satoshi Kojima、Kouji Fujitomo、Yoshihiro Shinohara、Makoto Shimizu、Katsuo Ohkata

  DOI：10.1016/s0040-4039(00)01743-3

  日期：2000.12

  The reaction of various mono-substituted methylidenemalononitriles with (-)-8-phenylmenthyl alpha -pyridiniumacetate in the presence of base afforded the corresponding dicyanocyclopropane compounds with exclusive trans-selectivity and good diastereoselectivity (up to 86.14). The stereochemistry of the major products were determined to be of 1R configuration by X-ray structural analysis of the crystalline tuans -2,2-dicyano-3-(4-pyridyl)cyclopropanecarboxylate. The geometric and diastereofacial selectivities were rationalized assuming anti-periplanar approach in the open-chain model, followed by epimerization and then cyclization to give the cyclopropane compounds. (C) 2000 Elsevier Science Ltd. All rights reserved.