methyl N-(diphenylmethyl)iminoacetate | 173201-94-0

• 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-(diphenylmethyl)iminoacetate
• 英文别名: N-benzhydryl-glyoxylic acid imine methyl ester
• CAS: 173201-94-0
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: RAYLELVERLVXCS-SFQUDFHCSA-N

物化性质

• 沸点：
  357.6±52.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.02
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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-(diphenylmethyl)iminoacetate 在 sodium hydroxide 、 氨 、 四丁基硫酸氢铵 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.5h， 生成
  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：

  2-羟基-2-甲氧基乙酸甲酯 、 二苯甲胺 以 甲苯 为溶剂， 反应 1.0h， 生成 methyl N-(diphenylmethyl)iminoacetate
  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

文献信息

• [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。
• PROCESS FOR THE PREPARATION OF (S)-2-AMINO-5-CYCLOPROPYL-4,4-DIFLUOROPENTANOIC ACID AND ALKYL ESTERS AND ACID SALTS THEREOF
  申请人：Hart Barry

  公开号：US20110046406A1

  公开（公告）日：2011-02-24

  The present invention relates to a process for the preparation of alkyl esters of (S)-2-amino-5-cyclopropyl-4,4-difluoropentanoic acid, which are intermediates useful in the synthesis of (S)-N-(1-cyanocyclopropyl)-5-cyclopropyl-4,4-difluoro-2-(S)-2,2,2-trifluoro-1-(4-fluorophenyl)ethylamino)pentanamide and related compounds, which are compounds that are cysteine protease inhibitors.

  本发明涉及一种制备(S)-2-氨基-5-环丙基-4,4-二氟戊酸烷基酯的方法，该方法是合成(S)-N-(1-氰基环丙基)-5-环丙基-4,4-二氟-2-(S)-2,2,2-三氟-1-(4-氟苯基)乙基氨基戊酰胺及相关化合物的中间体，这些化合物是半胱氨酸蛋白酶抑制剂。
• Synthesis of 2-Azetidiniminium Salts. 1. Diastereoselectivity in Keteniminium Triflate/Imine Cycloadditions
  作者：Gaetano Barbaro、Arturo Battaglia、Cristiana Bruno、Patrizia Giorgianni、Andrea Guerrini

  DOI：10.1021/jo9608782

  日期：1996.1.1

  A systematic study of the synthesis of 2-azetidiniminium triflates, by annulation of aldimines with iminium salts derived from tertiary carboxamides and trifluoromethanesulfonic anhydride, has been carried out. The stereochemical output of a number of 2-azetidiniminium triflates is compared with that of the corresponding chloride salts synthesized by reaction of the same imines with a-chloro iminium chlorides. As a general rule, the stereochemical output of the reactions involving a-chloro iminium chlorides is in stark contrast to that of the corresponding triflates: while the chloride salts are trans stereoselective, the triflates show a preference for the cis products. The stereochemistry of the reactions involving the triflates has been examined in light of the structure of the reagents. Clear trends for a preferential formation of cis or trans products with the steric and electronic demand of the imine have been observed. By contrast, no correlation of the product distribution with the steric demand of the amide could be made. The transient formation of a keteniminium triflate intermediate has been suggested. According to this model, the annulation of the imine with the keteniminium triflates occurs with a mechanism closely similar to that observed in the Staudinger reaction. A comparison between the reactions involving the bona fide keteniminium triflates, and the corresponding isoelectronic ketenes with the same, or structurally closely related, imines has also been made. This comparison is performed in light of Georg's stereochemical rules that are used to explain, or predict, the stereochemical output of the Staudinger reaction.
• 1,5-Asymmetric induction in reactions between 4- and 5-alkoxypent-2-enyl(tributyl)stannanes and achiral 1-alkoxycarbonylimines
  作者：David J Hallett、Eric J Thomas

  DOI：10.1016/0957-4166(95)00337-o

  日期：1995.10

  Tin(IV) chloride promoted reactions of 4- and 5-alkoxypent-2-enyl(tributyl)stannanes 1, 11 and 15 and 1-alkoxycarbonylimines 2 proceed with excellent 1,5-asymmetric induction.
• The Effect of a tert-butyldimethylsilyl substituent on the 1,5-asymmetric induction found in reactions of 4- and 5-alkoxyallylstannanes with aldehydes and imines
  作者：Gregory W Bradley、David J Hallett、Eric J Thomas

  DOI：10.1016/0957-4166(95)00338-p

  日期：1995.10

  The 4-benzyloxy- and 4-tert-butyldimethylsilyloxy-pent-2-enylstannanes 6a and 6b show different stereoselectivity in tin(IV) chloride promoted reactions with aldehydes and imines.