methyl N-benzoyl-β-phenylphenylalaninate | 305819-43-6

• 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-benzoyl-β-phenylphenylalaninate
• 英文别名: methyl 2-benzamido-3,3-diphenylpropanoate
• CAS: 305819-43-6
• 化学式: C₂₃H₂₁NO₃
• 分子量: 359.425
• InChiKey: LLQLTDIDFGSGLR-UHFFFAOYSA-N

物化性质

• 熔点：
  162 °C(Solv: methanol (67-56-1))
• 沸点：
  576.8±50.0 °C(Predicted)
• 密度：
  1.168±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl N-benzoyl-β-phenylphenylalaninate 在 盐酸 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 24.0h， 以90%的产率得到2-氨基-3,3-二苯基丙酸盐酸盐
  参考文献：
  名称：

  Synthesis of enantiomerically pure β,β-diphenylalanine (Dip) and fluorenylglycine (Flg)

  摘要：

  A new strategy for the preparation of both enantiomers of two phenylalanine analogues, beta,beta-diphenylalanine and fluorenylglycine, has been developed. The combination of a high yielding racemic synthesis and a very efficient resolution procedure has provided significant amounts of each amino acid in enantiomerically pure form and suitably protected for use in peptide synthesis. This methodology can be easily applied to the preparation of larger quantities of enantiopure compounds. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.08.007
• 作为产物：
  描述：

  methyl 2-benzamido-3,3-diphenylpropenoate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 48.0h， 以100%的产率得到methyl N-benzoyl-β-phenylphenylalaninate
  参考文献：
  名称：

  Synthesis of enantiomerically pure β,β-diphenylalanine (Dip) and fluorenylglycine (Flg)

  摘要：

  A new strategy for the preparation of both enantiomers of two phenylalanine analogues, beta,beta-diphenylalanine and fluorenylglycine, has been developed. The combination of a high yielding racemic synthesis and a very efficient resolution procedure has provided significant amounts of each amino acid in enantiomerically pure form and suitably protected for use in peptide synthesis. This methodology can be easily applied to the preparation of larger quantities of enantiopure compounds. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.08.007

文献信息

• Photochemical alkylation of glycine leading to phenylalanines
  作者：Haydn S Knowles、Keith Hunt、Andrew F Parsons

  DOI：10.1016/s0040-4039(00)01175-8

  日期：2000.9

  UV photolysis of protected glycines in the presence of di-tert-butyl peroxide, benzophenone and substituted toluenes is shown to lead to selective alkylation at the α-position. Phenylalanines are isolated in yields of generally >50% (based on recovered starting material).

  在过氧化二叔丁基，二苯甲酮和取代的甲苯的存在下，受保护的甘氨酸的紫外线光解显示可导致α位的选择性烷基化。分离出苯丙氨酸的产率通常> 50％（基于回收的起始原料）。
• A photochemical approach to phenylalanines and related compounds by alkylation of glycine
  作者：Haydn S Knowles、Keith Hunt、Andrew F Parsons

  DOI：10.1016/s0040-4020(01)00783-9

  日期：2001.9

  Phenylalanines can be prepared on UV photolysis of protected glycines in the presence of di-tert-butyl peroxide, substituted toluenes and the photosensitiser benzophenone. These reactions, which lead to highly selective mono-alkylation at the α-position of glycines, involve coupling of captodative α-glycine radicals with benzyl radicals. This method can be used to selectively alkylate a variety of

  苯丙氨酸可在过氧化二叔丁基，取代的甲苯和光敏剂二苯甲酮的存在下，通过紫外线对受保护的甘氨酸进行光解而制得。这些导致甘氨酸的α-位置高度选择性的单烷基化的反应涉及将captodativeα-甘氨酸自由基与苄基自由基偶联。该方法可用于在中性反应条件下，使用一系列取代的甲苯选择性地烷基化各种甘氨酸衍生物。
• Synthesis of enantiomerically pure β,β-diphenylalanine (Dip) and fluorenylglycine (Flg)
  作者：Soledad Royo、Ana I. Jiménez、Carlos Cativiela

  DOI：10.1016/j.tetasy.2006.08.007

  日期：2006.9

  A new strategy for the preparation of both enantiomers of two phenylalanine analogues, beta,beta-diphenylalanine and fluorenylglycine, has been developed. The combination of a high yielding racemic synthesis and a very efficient resolution procedure has provided significant amounts of each amino acid in enantiomerically pure form and suitably protected for use in peptide synthesis. This methodology can be easily applied to the preparation of larger quantities of enantiopure compounds. (c) 2006 Elsevier Ltd. All rights reserved.