(S)-tert-butyl 2-[(diphenylmethylidene)amino]-5-phenyl-5-oxopentanoate | 1170240-93-3

• 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: (S)-tert-butyl 2-[(diphenylmethylidene)amino]-5-phenyl-5-oxopentanoate
• 英文别名: (S)-tert-butyl 2-((diphenylmethylene)amino)-5-oxo-5-phenylpentanoate；tert-butyl (S)-2-(diphenylmethylenamino)-5-oxo-5-phenylpentanoate；tert-butyl (2S)-2-(benzhydrylideneamino)-5-oxo-5-phenylpentanoate
• CAS: 1170240-93-3
• 化学式: C₂₈H₂₉NO₃
• 分子量: 427.543
• InChiKey: NITZFONIGWQYQG-DEOSSOPVSA-N

物化性质

• 沸点：
  554.9±50.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  55.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-tert-butyl 2-[(diphenylmethylidene)amino]-5-phenyl-5-oxopentanoate 在 水 、 柠檬酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以75%的产率得到(S)-2-tert-butoxycarbonyl-5-phenyl-3,4-dihydro-2H-pyrrole
  参考文献：
  名称：

  Application of asymmetric phase-transfer catalysis in the enantioselective synthesis of cis-5-substituted proline esters

  摘要：

  A simple, highly stereoselective three-step sequence for the enantioselective synthesis of cis-5-substituted praline esters is described. This sequence features an asymmetric PTC Michael addition, followed by acid catalysed imine exchange and catalytic hydrogenation. Application of this chemistry in the synthesis of the nonpeptide cholecystokinin antagonist (+)-RP-66803 11 is also described. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.09.075
• 作为产物：
  描述：

  N-二苯亚甲基-甘氨酸叔丁酯 、 1-苯基-2-丙烯基-1-酮 在 2,4,6-三甲酚 、 potassium hydroxide 、 (2S,4S,5R)-1-Anthracen-9-ylmethyl-2-((R)-benzyloxy-quinolin-4-yl-methyl)-5-ethyl-1-azonia-bicyclo[2.2.2]octane; bromide 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以63%的产率得到(S)-tert-butyl 2-[(diphenylmethylidene)amino]-5-phenyl-5-oxopentanoate
  参考文献：
  名称：

  Application of asymmetric phase-transfer catalysis in the enantioselective synthesis of cis-5-substituted proline esters

  摘要：

  A simple, highly stereoselective three-step sequence for the enantioselective synthesis of cis-5-substituted praline esters is described. This sequence features an asymmetric PTC Michael addition, followed by acid catalysed imine exchange and catalytic hydrogenation. Application of this chemistry in the synthesis of the nonpeptide cholecystokinin antagonist (+)-RP-66803 11 is also described. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.09.075

文献信息

• Methylene-Bridged Bis(imidazoline)-Derived 2-Oxopyrimidinium Salts as Catalysts for Asymmetric Michael Reactions
  作者：Andrey E. Sheshenev、Ekaterina V. Boltukhina、Andrew J. P. White、King Kuok Mimi Hii

  DOI：10.1002/anie.201300614

  日期：2013.7.1

  In nothing flat: The title salts, having planar nitrogen centers, were utilized successfully as phase‐transfer catalysts for asymmetric Michael reactions of tert‐butyl glycinate benzophenone Schiff base with vinyl ketone and chalcone derivatives, thus providing excellent levels of diastereo‐ and enantiocontrol (see scheme).

  一言以蔽之：具有平面氮中心的标题盐被成功地用作甘氨酸叔丁酯二苯甲酮席夫碱与乙烯基酮和查尔酮衍生物的不对称迈克尔反应的相转移催化剂，从而提供了极好的非对映和对映控制水平（见方案）。
• Pentanidium-Catalyzed Enantioselective Phase-Transfer Conjugate Addition Reactions
  作者：Ting Ma、Xiao Fu、Choon Wee Kee、Lili Zong、Yuanhang Pan、Kuo-Wei Huang、Choon-Hong Tan

  DOI：10.1021/ja1098353

  日期：2011.3.9

  A new chiral entity, pentanidium, has been shown to be an excellent chiral phase-transfer catalyst. The enantioselective Michael addition reactions of tert-butyl glycinate-benzophenone Schiff base with various α,β-unsaturated acceptors provide adducts with high enantioselectivities. A successful gram-scale experiment at a low catalyst loading of 0.05 mol % indicates the potential for practical applications

  一种新的手性实体戊烷已被证明是一种出色的手性相转移催化剂。甘氨酸叔丁酯-二苯甲酮席夫碱与各种α,β-不饱和受体的对映选择性迈克尔加成反应提供了具有高对映选择性的加合物。在 0.05 mol% 的低催化剂负载下成功的克级实验表明该方法具有实际应用的潜力。磷酸甘氨酸酯类似物也可用作迈克尔供体，提供富含对映体的 α-氨基膦酸衍生物和 (S)-脯氨酸的膦酸类似物。
• Highly Enantioselective Conjugate Addition of Glycine Imines to Activated Alkenes Catalyzed by Amino-Acid-Derived Chiral Phosphonium Salts
  作者：Shan Wen、Xing Li、Weijun Yao、Abdul Waheed、Nisar Ullah、Yixin Lu

  DOI：10.1002/ejoc.201600794

  日期：2016.9

  Chiral quaternary phosphonium salts derived from amino acids were readily prepared and employed as phase-transfer catalysts for the highly enantioselective conjugate addition of glycine imines to various activated alkenes, including chalcones, acrylates, and vinyl ketones.

  源自氨基酸的手性季鏻盐很容易制备并用作相转移催化剂，用于甘氨酸亚胺与各种活化烯烃（包括查耳酮、丙烯酸酯和乙烯基酮）的高度对映选择性共轭加成。
• Asymmetric Ruthenium‐Catalyzed Hydroalkylation of Racemic Allylic Alcohols for the Synthesis of Chiral Amino Acid Derivatives
  作者：Xiaohui Zhang、Wei Ma、Jinyu Zhang、Weijun Tang、Dong Xue、Jianliang Xiao、Huaming Sun、Chao Wang

  DOI：10.1002/anie.202203244

  日期：2022.6.27

  Racemic allylic alcohols are converted into chiral amino acid derivatives via asymmetric hydroalkylation enabled by borrowing hydrogen catalysis. Mechanistic studies suggested that a single ruthenium chiral catalyst controls the stereoselectivity of two remote chiral centers through a dynamic kinetic asymmetric transformation and a diastereoselectivity amplification process of the product.

  外消旋烯丙醇通过借氢催化实现的不对称加氢烷基化转化为手性氨基酸衍生物。机理研究表明，单一的钌手性催化剂通过动态动力学不对称转变和产物的非对映选择性放大过程控制两个远程手性中心的立体选择性。
• Application of asymmetric phase-transfer catalysis in the enantioselective synthesis of cis-5-substituted proline esters
  作者：Barry Lygo、Christopher Beynon、Michael C. McLeod、Claude-Eric Roy、Charles E. Wade

  DOI：10.1016/j.tet.2010.09.075

  日期：2010.11

  A simple, highly stereoselective three-step sequence for the enantioselective synthesis of cis-5-substituted praline esters is described. This sequence features an asymmetric PTC Michael addition, followed by acid catalysed imine exchange and catalytic hydrogenation. Application of this chemistry in the synthesis of the nonpeptide cholecystokinin antagonist (+)-RP-66803 11 is also described. (C) 2010 Elsevier Ltd. All rights reserved.