isopropyl (S)-2-[(diphenylmethylidene)amino]-3-phenylpropanoate | 138892-11-2

• 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: isopropyl (S)-2-[(diphenylmethylidene)amino]-3-phenylpropanoate
• 英文别名: isopropyl (S)-2-(diphenylmethyleneamino)-3-phenylpropanoate；isopropyl (S)-2-diphenylmethyleneamino-3-phenylpropanoate；propan-2-yl (2S)-2-(benzhydrylideneamino)-3-phenylpropanoate
• CAS: 138892-11-2
• 化学式: C₂₅H₂₅NO₂
• 分子量: 371.479
• InChiKey: SXHGFRLUEAWSKU-QHCPKHFHSA-N

物化性质

• 沸点：
  478.3±45.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  甘氨酸异丙酯 在 氢氧化钾 、 9,10-bis(9-OH-cinchonidin-1-iomethyl)anthracene 2Cl^(1-) 作用下， 以 氯仿 、 水 、 甲苯 为溶剂， 反应 9.0h， 生成 isopropyl (S)-2-[(diphenylmethylidene)amino]-3-phenylpropanoate
  参考文献：
  名称：

  New dimeric anthracenyl-derived Cinchona quaternary ammonium salts as phase-transfer catalysts for the asymmetric synthesis of α-amino acids

  摘要：

  New dimeric cinchonidine- and cinchonine-derived ammonium salts which incorporate a dimethylanthracenyl bridge have been prepared and used as phase-transfer catalysts in the asymmetric alkylation of N-(diphenylmethylene)glycine esters in good yields and tip to 90% ee. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00211-2

文献信息

• Oxygen Alkylation of Schiff Base Derivatives of Amino Acids
  作者：Martin J. O'Donnell、Gwendolyn K. Cook、David B. Rusterholz

  DOI：10.1055/s-1991-26625

  日期：——

  Higher imine esters 1a-h and 7a-b of amino acids and dipeptides are prepared in 68-91% yield by saponification of the benzophenone Schiff base methyl esters 3a-d and 6 using phase-transfer techniques followed by O-alkylation with an alkyl halide. The procedure occurs with retention of configuration at the α-carbon except with phenylglycine derivatives.

  氨基酸和二肽的高亚胺酯1a-h和7a-b通过皂化苯甲酮席夫碱甲酯3a-d和6，采用相转移技术，随后与烷基卤进行O-烷基化，产率在68-91%之间。该过程在α-碳上保留构型，除了苯基甘氨酸衍生物外。
• Chiroptical properties and applications in PTC of new dendritic cinchonidine-derived ammonium salts
  作者：Gabriela Guillena、Robert Kreiter、Rob van de Coevering、Robertus J.M. Klein Gebbink、Gerard van Koten、Patricia Mazón、Rafael Chinchilla、Carmen Nájera

  DOI：10.1016/j.tetasy.2003.08.030

  日期：2003.11

  Chiral nanosize molecules, derived from cinchonidine and Fréchet dendritic wedges up to generation three, have been synthesized. The chiroptical properties, optical rotation and circular dichroism of these systems have been studied. These chiral dendritic molecules have been used as phase transfer catalysts in the alkylation of a glycine imine ester, showing a promising level of asymmetric induction

  已经合成了从辛可尼定和弗雷谢特树状楔形物衍生到第三代的手性纳米级分子。已经研究了这些系统的手性，旋光性和圆二色性。这些手性树突状分子已被用作甘氨酸亚胺酯的烷基化中的相转移催化剂，显示出令人期待的不对称诱导水平。
• Polymer-Supported Cinchona Alkaloid-Derived Ammonium Salts as Recoverable Phase-Transfer Catalysts for the Asymmetric Synthesis of α-Amino Acids
  作者：Rafael Chinchilla、Patricia Mazón、Carmen Nájera

  DOI：10.3390/90500349

  日期：——

  of polymer-supported chiral ammonium salts which have been employed as phase-transfer catalysts in the asymmetric benzylation of an N-(diphenylmethylene)glycine ester. These new polymeric catalysts can be easily recovered by simple filtration after the reaction and reused. The best ee's were achieved when Merrifield resin-anchored cinchonidinium ammonium salts were employed.

  辛可尼定、奎宁和N-甲基麻黄碱等生物碱已使用聚合卤化苄进行N-烷基化或共聚然后N-烷基化，从而提供了一系列聚合物负载的手性铵盐，这些手性铵盐已用作相转移催化剂N-(二苯基亚甲基)甘氨酸酯的不对称苄基化。这些新型聚合物催化剂可以在反应后通过简单过滤轻松回收并重复使用。当使用 Merrifield 树脂锚定的辛可尼丁铵盐时，获得了最佳的 ee。
• Polystyrene-AnchoredCinchona Ammonium Salts: Easily Recoverable Phase-Transfer Catalysts for the Asymmetric Synthesis ofα-Amino Acids
  作者：Rafael Chinchilla、Patricia Mazón、Carmen Nájera

  DOI：10.1002/adsc.200404093

  日期：2004.8

  cross-linked polystyrene (Merrifield resin) or grafted polystyrene (SynPhaseTM Lanterns) affording polymer-supported chiral ammonium salts which are employed as phase-transfer catalysts in the asymmetric alkylation of N-(diphenylmethylene)glycine esters. These new polymeric catalysts can be easily recovered after the reaction by simple filtration and reused.

  辛可尼定，环氧庚烷，辛可宁或奎宁已被N固定在交联的聚苯乙烯（Merrifield树脂）或接枝的聚苯乙烯（SynPhase TM Lanterns）上，提供了聚合物负载的手性铵盐，这些盐在N的不对称烷基化反应中用作相转移催化剂-（二苯基亚甲基）甘氨酸酯。这些新的聚合催化剂可以在反应后通过简单的过滤容易地回收并再利用。
• Unexpected metal base-dependent inversion of the enantioselectivity in the asymmetric synthesis of α-amino acids using phase-transfer catalysts derived from cinchonidine
  作者：Patricia Mazón、Rafael Chinchilla、Carmen Nájera、Gabriela Guillena、Rob Kreiter、Robertus J.M. Klein Gebbink、Gerard van Koten

  DOI：10.1016/s0957-4166(02)00611-0

  日期：2002.10

  dNew cinchonidinium salts bearing a 3,5-dialkoxybenzyl group show an alkaline metal base-dependent reversal of enantioselectivity when used as phase-transfer catalysts in the asymmetric alkylation of N-(diphenylmethylene)glycine isopropyl ester with benzyl bromide. The use of potassium hydroxide as base in this alkylation reaction afforded the (S)-enantiomer, whereas using sodium hydroxide under the same conditions afforded the corresponding (R)-enantiomer. (C) 2002 Elsevier Science Ltd. All rights reserved.