N,N-二苄基-2-苯基甘氨酸甲酯 | 345579-56-8

• 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
• 中文名称: N,N-二苄基-2-苯基甘氨酸甲酯
• 英文名称: N,N-dibenzyl-2-phenylglycine methyl ester
• 英文别名: Methyl 2-(dibenzylamino)-2-phenylacetate
• CAS: 345579-56-8
• 化学式: C₂₃H₂₃NO₂
• 分子量: 345.441
• InChiKey: YGLZUMLZWOSPSK-UHFFFAOYSA-N

物化性质

• 沸点：
  446.1±33.0 °C(Predicted)
• 密度：
  1.133±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N-二苄基-2-苯基甘氨酸甲酯 在 palladium dihydroxide 盐酸 、 lithium aluminium tetrahydride 、 氢气 、 sodium cyanoborohydride 、 溶剂黄146 、 silver(l) oxide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， -78.0~20.0 ℃ 、344.74 kPa 条件下， 反应 54.0h， 生成 1-{4-[3-Amino-4-(3,5-bis-trifluoromethyl-benzyloxy)-3-phenyl-butylamino]-piperidin-1-yl}-ethanone
  参考文献：
  名称：

  Cyclic urea derivatives as potent NK1 selective antagonists

  摘要：

  A series of novel five- and six-membered ring urea derivatives have been described as potent and selective NK1 receptor antagonists. Several compounds in this series exhibited good oral activity and brain penetration. Syntheses of these compounds are also described herein. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.111
• 作为产物：
  描述：

  methyl (E)-2-(hydroxyimino)-2-phenylacetate 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.25h， 生成 N,N-二苄基-2-苯基甘氨酸甲酯
  参考文献：
  名称：

  Double nucleophilic N-alkylation of α-oxime-esters with Grignard reagents

  摘要：

  Double nucleophilic N-alkylation of alpha-oxime-esters, affording N,N-dialkyl-alpha-amino acids is herein described. Grignard reagents accomplished double N-alkylations via umpolung and various N.N-dialkylated alpha-amino acids were successfully synthesized in 15 min. Both electron-withdrawing sulfonyl groups and electron-donating silyl and methyl groups on oximes were available. Alkylmagnesium species and (E)-configuration of alpha-oxime-ester were essential to this cascade reaction. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.08.091

文献信息

• Copper-Catalyzed Amination of Silyl Ketene Acetals with <i>N</i>-Chloroamines
  作者：Tomoya Miura、Masao Morimoto、Masahiro Murakami

  DOI：10.1021/ol302331k

  日期：2012.10.19

  A copper(I)/2,2′-bipyridyl complex catalyzes an amination reaction of silyl ketene acetals with N-chloroamines, presenting a new preparative method of α-amino esters.

  铜（I）/ 2,2'-联吡啶配合物催化甲硅烷基乙烯酮缩醛与N-氯胺的胺化反应，为α-氨基酯的制备提供了一种新的方法。
• Evidence for the intermediacy of chromium-ketene complexes in the synthesis of .beta.-lactams by the photolytic reaction of chromium-carbene complexes with imines. Use in amino acid synthesis
  作者：Louis S. Hegedus、Guy. De Weck、Stan. D'Andrea

  DOI：10.1021/ja00215a019

  日期：1988.3
• Microwave assisted Petasis boronic-Mannich reactions
  作者：Neville J. McLean、Heather Tye、Mark Whittaker

  DOI：10.1016/j.tetlet.2003.11.092

  日期：2004.1

  We have used a design of experiments (DOE) approach to optimise rapidly a set of microwave assisted conditions for the Petasis reaction. The optimal conditions involved the microwave heating of the reaction components in dichloromethane (1 M concentration) at 120 degreesC for 10 min in a focussed microwave (CEM Explorer). These conditions were successfully applied to a range of Petasis reactions employing either glyoxylic acid or salicylaldehyde as the carbonyl component along with a number of aryl/heteroaryl boronic acids and amine components. (C) 2003 Elsevier Ltd. All rights reserved.
• Double nucleophilic N-alkylation of α-oxime-esters with Grignard reagents
  作者：Yusuke Mizutani、Hiroki Tanimoto、Tsumoru Morimoto、Yasuhiro Nishiyama、Kiyomi Kakiuchi

  DOI：10.1016/j.tetlet.2012.08.091

  日期：2012.10

  Double nucleophilic N-alkylation of alpha-oxime-esters, affording N,N-dialkyl-alpha-amino acids is herein described. Grignard reagents accomplished double N-alkylations via umpolung and various N.N-dialkylated alpha-amino acids were successfully synthesized in 15 min. Both electron-withdrawing sulfonyl groups and electron-donating silyl and methyl groups on oximes were available. Alkylmagnesium species and (E)-configuration of alpha-oxime-ester were essential to this cascade reaction. (C) 2012 Elsevier Ltd. All rights reserved.
• Cyclic urea derivatives as potent NK1 selective antagonists
  作者：Ho-Jane Shue、Xiao Chen、Neng-Yang Shih、David J. Blythin、Sunil Paliwal、Ling Lin、Danlin Gu、John H. Schwerdt、Sapna Shah、Gregory A. Reichard、John J. Piwinski、Ruth A. Duffy、Jean E. Lachowicz、Vicki L. Coffin、Fei Liu、Amin A. Nomeir、Cynthia A. Morgan、Geoffrey B. Varty

  DOI：10.1016/j.bmcl.2005.05.111

  日期：2005.9

  A series of novel five- and six-membered ring urea derivatives have been described as potent and selective NK1 receptor antagonists. Several compounds in this series exhibited good oral activity and brain penetration. Syntheses of these compounds are also described herein. (c) 2005 Elsevier Ltd. All rights reserved.