N-carbomethoxy-triphenylphosphinimine | 40438-23-1

• 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-carbomethoxy-triphenylphosphinimine
• 英文别名: Carbamic acid, (triphenylphosphoranylidene)-, methyl ester；methyl N-(triphenyl-λ5-phosphanylidene)carbamate
• CAS: 40438-23-1
• 化学式: C₂₀H₁₈NO₂P
• 分子量: 335.342
• InChiKey: CLVUPMNCXUYZMW-UHFFFAOYSA-N

物化性质

• 熔点：
  136-137 °C
• 沸点：
  466.4±28.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-carbomethoxy-triphenylphosphinimine 以52%的产率得到
  参考文献：
  名称：

  NICLAS H.-J.; MARTIN D., TETRAHEDRON, 1978, 34, NO 6, 703-706

  摘要：

  DOI：
• 作为产物：
  描述：

  2-三(苯基)膦亚基乙酰胺 在 三乙胺 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 生成 N-carbomethoxy-triphenylphosphinimine
  参考文献：
  名称：

  New phosphonium ylides by functionalization of triphenylphosphoranylideneacetamide

  摘要：

  Triphenylphosphoranylideneacetamide undergoes Michael reactions with several acceptors, giving rise, apart from the normal Michael adducts, to the formation of different products like glutarimide ylides and stabilized iminophosphoranes. Wittig reactions with these new ylides lead to a variety of alpha,beta-unsaturated carbonyl compounds.

  DOI：

  10.1016/s0040-4039(00)91662-9

文献信息

• Optically Active Aromatic and Heteroaromatic α-Amino Acids by a One-Pot Catalytic Enantioselective Addition of Aromatic and Heteroaromatic C−H Bonds to α-Imino Esters
  作者：Steen Saaby、Pau Bayón、Pompiliu S. Aburel、Karl Anker Jørgensen

  DOI：10.1021/jo0256787

  日期：2002.6.1

  procedure for the synthesis of non-natural aromatic and heteroaromatic alpha-amino acids is reported. Starting from readily available starting materials and application of a chiral BINAP-Cu(I) catalyst, the optically active products are formed with readily removable N-protecting groups. The scope of the reaction is demonstrated by the addition of substituted furans, thiophenes, pyrroles, and aromatic compounds

  报道了一种用于合成非天然芳族和杂芳族α-氨基酸的实用的一锅催化对映选择性方法的开发。从容易获得的起始原料和手性BINAP-Cu（I）催化剂的应用开始，形成具有易于除去的N-保护基的旋光产物。通过以高收率向N-烷氧基羰基-α-亚氨基酯中添加取代的呋喃，噻吩，吡咯和芳香族化合物来证明反应的范围，对呋喃的对映选择性高达96％ee，对呋喃的对映选择性高达93％ee。噻吩，98％为芳香族化合物。保护基易于除去，并且证明了芳族和杂芳族α-氨基酸的各种转化。
• Synthesis of optically pure (R)- and (S)-α-trifluoromethyl-alanine
  作者：Pierfrancesco Bravo、Silvia Capelli、Stefano Valdo Meille、Fiorenza Viani、Matteo Zanda、Valery P. Kukhar、Vadim A. Soloshonok

  DOI：10.1016/s0957-4166(00)86276-x

  日期：1994.10

  (+)-(R)- and (-)-(S)-3,3,3-trifluoro-2-methyl-alanine (1) were synthesized from (+)-(R)-methyl-p-tolylsulphoxide (5) and N-alkoxycarbonylimino derivatives 4 of methyl 3,3,3-trifluoropyruvate (3). The absolute configuration was determined by X-ray analyses of two synthetic intermediates (2S,R(S))-6a and (2R,R(S))-6c.

  (+)-(R)-和(-)-(S)-3,3,3-三氟-2-甲基丙氨酸(1)是由(+)-(R)-甲基-p-甲苯基亚硫酸酯(5)和来自甲基3,3,3-三氟丙酮酸甲酯(3)的N-烷氧基甲酰亚胺衍生物(4)合成的。绝对构型通过两种合成中间体(2S,R(S))-6a和(2R,R(S))-6c的X射线分析确定。
• Enantioselective reduction of CO and CN compounds with NADH model N,N,1,2,4-pentamethyl-1,4-dihydronicotinamide
  作者：Jos P. Versleijen、Mireille S. Sanders-Hovens、Sylvia A. Vanhommerig、Jozef A. Vekemans、Emmo M. Meijer

  DOI：10.1016/s0040-4020(01)87253-7

  日期：1993.8

  The scope and mechanism of enantioselective hydride transfer from NADH model 4 to prochiral CO and CN compounds were investigated. Efficient chirality transfer from 4 to α-keto esters and α-methoxycarbonylimino esters was achieved. The resemblance in reactivity and stereochemistry of the prochiral CO and CN-CO2Me functionalities in the hydride transfer reaction is attributed to the intervention

  研究了NADH 4型对映体选择性氢化物向前手性CO和CN化合物转移的范围和机理。实现了从4到α-酮酸酯和α-甲氧基羰基亚氨基酯的有效手性转移。在反应性和前手性CO和CN-CO的立体化学结构的相似2在氢化物转移反应我官能归因于相似的Mg的干预（CLO 4）2介导的三元复合物。
• A Convenient Synthesis of Triphenylphosphine Acylimides Using<i>N</i>-Lithiated Triphenylphosphine Imide
  作者：H. J. Cristau、E. Manginot、E. Torreilles

  DOI：10.1055/s-1991-26471

  日期：——

  A series of triphenylphosphine acylimides and N-(triphenylphosphoranylidene) carbamates have been readily prepared by direct acylation of the N-lithiated triphenylphosphine imide.

  通过直接酰化 N-亚硫酸化三苯基膦亚胺，可以很容易地制备出一系列三苯基膦酰亚胺和 N-（三苯基膦亚基）氨基甲酸酯。
• Amino Acids, XI: (±)Pipecolic Acid Derivatives - Part 1: The [4+2] Cycloaddition Pathway
  作者：Claus Herdeis、Wolfram Engel

  DOI：10.1002/ardp.19923250708

  日期：——

  [4+2] Cycloadditions of various dienes 1 with the acceptor‐substituted imines 2 furnished the 4‐oxo‐piperidine‐2,2‐dicarboxylate derivatives 3, 5, 11, 12. All efforts to get the regio‐isomeric 5‐oxo‐derivatives (Scheme 2) by variation of the reaction conditions and substitution pattern of 1 and 2 resulted in differing amounts of ring‐open products 4, 6, 8, 10. This is in contradiction to results of

  [4 + 2] 各种二烯 1 与受体取代亚胺 2 的环加成得到 4-氧代-哌啶-2,2-二羧酸衍生物 3, 5, 11, 12。所有努力获得区域-异构体 5-氧代- 衍生物（方案 2）通过改变反应条件和 1 和 2 的取代模式导致不同数量的开环产物 4、6、8、10。这与另一组 4a) 的结果相矛盾。