N-(diphenylmethyl)ethanimine | 169698-45-7

• 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: N-(diphenylmethyl)ethanimine
• CAS: 169698-45-7
• 化学式: C₁₅H₁₅N
• 分子量: 209.291
• InChiKey: LBFUDPSODRNJKS-APQPDGGLSA-N

物化性质

• 沸点：
  319.7±42.0 °C(Predicted)
• 密度：
  0.94±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.87
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  12.36
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  N-(diphenylmethyl)ethanimine 在 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 paraffin 、 苯 为溶剂， 反应 3.0h， 生成 benzyl N-diphenylmethyl-N-vinylcarbamate
  参考文献：
  名称：

  对新一代喹诺酮羧酸DU-6859关键成分的合成研究。1.通过光学拆分合成（1 R，2 S）-2-氟环丙胺

  摘要：

  通过使用N-苄基-N-乙烯基氨基甲酸酯与锌-单氟乙炔化合物进行高度顺式选择性环丙烷化，形成的N-苄基-N-（顺式-2-氟环丙基）氨基甲酸酯脱保护以及所得产物的光学拆分，可以实现标题合成。 dl-顺式-2-氟环丙胺通过使用氯甲酸l-薄荷基酯作为拆分剂。关键的环丙烷化反应观察到的顺式选择性可以通过弯曲的过渡态模型来解释。

  DOI：

  10.1016/s0040-4020(01)89665-4
• 作为产物：
  描述：

  乙醛 、 二苯甲胺 在 magnesium sulfate 作用下， 以 乙醚 为溶剂， 反应 12.0h， 生成 N-(diphenylmethyl)ethanimine
  参考文献：
  名称：

  对新一代喹诺酮羧酸DU-6859关键成分的合成研究。1.通过光学拆分合成（1 R，2 S）-2-氟环丙胺

  摘要：

  通过使用N-苄基-N-乙烯基氨基甲酸酯与锌-单氟乙炔化合物进行高度顺式选择性环丙烷化，形成的N-苄基-N-（顺式-2-氟环丙基）氨基甲酸酯脱保护以及所得产物的光学拆分，可以实现标题合成。 dl-顺式-2-氟环丙胺通过使用氯甲酸l-薄荷基酯作为拆分剂。关键的环丙烷化反应观察到的顺式选择性可以通过弯曲的过渡态模型来解释。

  DOI：

  10.1016/s0040-4020(01)89665-4

文献信息

• COMPOUNDS AND RELATED METHODS OF USE
  申请人：Jacobsen Eric N.

  公开号：US20130066109A1

  公开（公告）日：2013-03-14

  Described herein are compounds of formula (I), related compositions, and their use, for example in the formation of α-amino acids or a precursor thereof such as an α-aminonitrile.

  本文描述了式（I）的化合物、相关组合物及其用途，例如在形成α-氨基酸或其前体（如α-氨基腈）中的应用。
• PROCESS FOR THE PREPARATION OF OPTICALLY ACTIVE 1-AMINOPHOSPHONIC ACID DERIVATIVES AND NOVEL PHOSPHONATE COMPOUNDS
  申请人：HOKKO CHEMICAL INDUSTRY CO. LTD.

  公开号：EP0877028A1

  公开（公告）日：1998-11-11

  Provided is a process for the preparation of an optically active (R)- or (S)-1-aminophosphonic acid derivative of the general formula (Ia) or (Ib) given below, which process comprises reacting an amino-protected imine having general formula (II): R1-N=CHR2 where R1 is diphenylmethyl group or the like and R2 is an alkyl group or the like, with a phosphonic acid ester in the presence of an asymmetric catalyst consisting of a rare earth element-alkali metal-binaphthol complex, to produce an (R)- or (S)-N-protected-1-aminophosphonate compound, and then subjecting the phosphonate compound to catalytic reduction with hydrogen and to acidic hydrolysis. There are also provided novel intermediates, and a process of preparing an asymmetric catalyst consisting of a rare element-alkali metal-binaphthol complex.

  本发明提供了一种制备下式(Ia)或(Ib)的光学活性(R)-或(S)-1-氨基膦酸衍生物的工艺，该工艺包括使具有通式(II)的氨基保护亚胺反应：R1-N=CHR2 其中 R1 为二苯基甲基或类似基团，R2 为烷基或类似基团，在由稀土元素-碱金属-联萘酚络合物组成的不对称催化剂存在下，与膦酸酯反应，生成(R)-或(S)-N-保护的-1-氨基膦酸盐化合物，然后将膦酸盐化合物用氢气催化还原并进行酸性水解。 此外，还提供了新型中间体，以及由稀有元素-碱金属-萘酚络合物组成的不对称催化剂的制备方法。
• Preparation of phosphinodipeptide analogs as building blocks for pseudopeptides synthesis
  作者：Henri-Jean Cristau、Agnès Coulombeau、Arielle Genevois-Borella、Frédéric Sanchez、Jean-Luc Pirat

  DOI：10.1016/s0022-328x(01)01238-4

  日期：2002.2

  A simple and effective preparation of phosphinodipeptides, in good overall yields, has been developed, This one pot procedure, allowing the variation of the substituents in alpha and/or beta position to the phosphorus atom and also in alpha position to the nitrogen atom, consists in the addition of alkyl hypophosphites to imines. followed by Michael-addition on acrylates. To show the value of phosphinodipeptides analogs I as synthetic intermediates, selective deprotections of the three functional groups are described. (C) 2002 Elsevier Science B.V. All rights reserved.
• 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.
• Tamura Osamu, Hashimoto Masaru, Kobayashi Yuko, Katoh Tadashi, Nakatani K+, Tetrahedron, 50 (1994) N 13, S 3889-3904
  作者：Tamura Osamu, Hashimoto Masaru, Kobayashi Yuko, Katoh Tadashi, Nakatani K+

  DOI：——

  日期：——