methyl 2-(1-phenylethylamino)butanoate | 65768-17-4

• 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: methyl 2-(1-phenylethylamino)butanoate
• 英文别名: Butanoic acid, 2-[[(1S)-1-phenylethyl]amino]-, methyl ester, (2S)-；methyl (2S)-2-[[(1S)-1-phenylethyl]amino]butanoate
• CAS: 65768-17-4
• 化学式: C₁₃H₁₉NO₂
• 分子量: 221.299
• InChiKey: KWPWOWNUGHMEDM-JQWIXIFHSA-N

物化性质

• 沸点：
  294.6±23.0 °C(Predicted)
• 密度：
  1.014±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  三乙基硼 、 methyl N-(1-phenylethyl)-α-iminoacetate 在 air 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 methyl 2-(1-phenylethylamino)butanoate 、 methyl 2-(1-phenylethylamino)butanoate
  参考文献：
  名称：

  Et3B- and Et2Zn-Mediated Radical Additions to Glyoxylate Imines, Compared Stereoinductions

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(00)00327-6

文献信息

• 1,3-Stereoinduction in Radical Additions to Glyoxylate Imines
  作者：Michèle P. Bertrand、Laurence Feray、Robert Nouguier、Lucien Stella

  DOI：10.1055/s-1998-1763

  日期：1998.7

  Addition of alkyl radicals to the acyclic glyoxylate imine 1 proceeded with a 70 : 30 stereoinduction, even at -78 °C. Addition to the cyclic imine 4b resulted in complete stereocontrol at -40 °C.

  在-78°C下，烷基自由基对非环状乙二醛亚胺1的加成反应形成了70:30的立体诱导产物。而在-40°C时，对环状亚胺4b的加成则实现了完全的立体控制。
• 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.