methyl N-(1-phenylethyl)-α-iminoacetate | 145774-77-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl N-(1-phenylethyl)-α-iminoacetate
• 英文别名: Methyl glyoxylate 1-phenylethylimine；N-(1-phenylethyl)-glyoxyl acid imine methyl ester
• CAS: 145774-77-2
• 化学式: C₁₁H₁₃NO₂
• 分子量: 191.23
• InChiKey: UXRHYUSIOTYRRH-XYOKQWHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.99
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  38.66
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl N-(1-phenylethyl)-α-iminoacetate 在 氨 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以76%的产率得到
  参考文献：
  名称：

  一种制备功能化的非天然α-H-α-氨基酸衍生物的新方法

  摘要：

  据报道基于亚氨基乙酸酯或酰胺的α-烷基化制备α-H-α-氨基酸的新方法。这些亚胺可通过乙醛酸酯与支链伯胺反应而容易地获得。随后与甲醇氨的反应得到相应的亚氨基乙酸酰胺。这些亚胺在碱性条件下与各种亲电试剂的α-烷基化反应，然后进行酸性水解，以高达93％的收率得到α-氨基酸，酯或酰胺。在手性PTC条件下进行α-烷基化可得到具有90％ee的单烷基化氨基酸。

  DOI：

  10.1016/j.tetlet.2006.08.096
• 作为产物：
  描述：

  乙醛酸甲酯 、 α-苯乙胺 在 molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 methyl N-(1-phenylethyl)-α-iminoacetate
  参考文献：
  名称：

  Reaction d'aza-diels-alder diastereoselective : utilisation de la 1-phenylethyl imine de glyoxylated d'alkyle pour la synthese de derives d'α-amino acides cycliques

  摘要：

  The use of trifluoroacetic acid-boron trifluoride combination is highly effective in dichloromethane for the activation of 1-phenylethylimine of methyl or ethyl glyoxylates as heterodienophiles in Diels-Alder cycloaddition reactions with a series of conjugated dienes. High regio-(meta:para) and stereo-(endo:exo) selectivities are observed at low temperature. Asymmetric induction is very high (>98%) with cyclopentadiene but remains low in the other cases.

  DOI：

  10.1016/s0040-4020(01)81187-x

文献信息

• Evaluation of phenylorganotellurium compounds as radical precursors in dialkylzinc-mediated radical addition to CN double bonds
  作者：Fabien Cougnon、Laurence Feray、Samantha Bazin、Michèle P. Bertrand

  DOI：10.1016/j.tet.2007.09.014

  日期：2007.11

  Diethylzinc-mediated radical addition to CN bonds was investigated in the presence of phenylorganotellurium compounds as radical precursors. As group transfer agents, secondary alkyl phenyl tellurides were shown to be about twice as reactive as the corresponding alkyl iodides towards ethyl radical. Their use was proven to be advantageous regarding both chemoselectivity and yield. The replacement of

  在苯基有机碲化合物作为自由基前体的存在下，研究了二乙基锌介导的向CN键的自由基加成反应。作为基团转移剂，仲烷基苯基碲化物的反应活性约为相应的烷基碘对乙基的两倍。事实证明，它们的使用在化学选择性和产率方面都是有利的。用二甲基锌代替二乙基锌在这些反应中没有优势。
• [EN] PROCESS FOR THE PREPARATION OF AN alpha-AMINO CARBONYL COMPOUND<br/>[FR] PROCEDE DE PREPARATION D'UN COMPOSE DOLLAR G(A)-AMINO CARBONYLE
  申请人：DSM IP ASSETS BV

  公开号：WO2004078702A1

  公开（公告）日：2004-09-16

  The invention relates to a process for the preparation of an α-amino carbonyl compound by reacting an imine starting material with a suitable electrophile in the presence of a base. This process has the advantage that the imine starting materials can be prepared from glyoxylic acid esters or glyoxylic acid ester derivatives and α-hydrogen containing primary amines, which are usually cheap and readily available. These imine starting materials can usually be prepared with a high yield and/or almost without the formation of any side products.

  该发明涉及一种通过在碱存在下，将亚胺起始物与适当的亲电试剂反应制备α-氨基羰基化合物的方法。这种方法的优点在于，亚胺起始物可以由乙酰乙酸酯或乙酰乙酸酯衍生物和α-氢含量的一级胺反应制备，这些原料通常便宜且易得。这些亚胺起始物通常可以高产率地制备，或几乎不形成任何副产物。
• Diethylzinc: A Chain-Transfer Agent in Intermolecular Radical Additions. A Parallel with Triethylborane
  作者：Michèle P. Bertrand、Laurence Feray、Robert Nouguier、P. Perfetti

  DOI：10.1021/jo9912404

  日期：1999.12.1

  In the presence of oxygen, diethylzinc can be used to promote radical additions to C=N bond containing radical accepters and to enones. In these reactions, it plays at the same time the role of the initiator and the role of the chain-transfer reagent. A parallel with triethylborane-mediated reactions is established. The methodology is restricted to secondary and tertiaryalkyl radicals generated from the corresponding alkyl iodides. It could not be extended either to C=C bond containing radical accepters such as methyl methacrylate and nitrocyclohexene or to diethylazodicarboxylate.
• Et3B- and Et2Zn-Mediated Radical Additions to Glyoxylate Imines, Compared Stereoinductions
  作者：Michèle P. Bertrand、Stéphanie Coantic、Laurence Feray、Robert Nouguier、Patricia Perfetti

  DOI：10.1016/s0040-4020(00)00327-6

  日期：2000.6

  1,3-Stereoinduction in the addition of alkyl radicals to glyoxylic imines derived from various chiral amines has been investigated. New synthetic methodologies involving Et3B and Et2Zn as mediators have been compared. Dihydro-1,4-oxazin-2-one (2b) gave the highest d.e. but no chemoselectivity. Open chain analogues derived from beta-alkoxyamines led to good stereoinduction when the reaction was performed with Et2Zn which is a bidentate complexing reagent. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Asymmetric aza-diels-alder reaction using the chiral 1-phenyl ethyl imine of methyl glyoxylate
  作者：L. Stella、H. Abraham、J. Feneau-Dupont、B. Tinant、J.P. Declercq

  DOI：10.1016/0040-4039(90)80136-a

  日期：1990.1