methyl 2-[(diphenylmethylene)amino]-3-(4-methylphenylsulfonamide)-3-(o-methylphenyl)propanoate | 1160052-52-7

• 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
• 英文名称: methyl 2-[(diphenylmethylene)amino]-3-(4-methylphenylsulfonamide)-3-(o-methylphenyl)propanoate
• 英文别名: methyl 2-[(diphenylmethylene)amino]-3-(o-methylphenyl)-3-(p-toluenesulfonylamino)propanoate；(2S,3S)-methyl 3-(2-methylphenyl)-2-(diphenylmethyleneamino)-3-(tosylamino)propanoate；methyl 2-[(diphenylmethylene)amino]-3-(o-methylphenyl)-3-(tosylamino)propanoate；methyl (2S,3S)-2-(benzhydrylideneamino)-3-(2-methylphenyl)-3-[(4-methylphenyl)sulfonylamino]propanoate
• CAS: 1160052-52-7
• 化学式: C₃₁H₃₀N₂O₄S
• 分子量: 526.656
• InChiKey: LFOIAKQYRROCNY-KYJUHHDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  93.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  二苯亚甲基甘氨酸甲酯 、 N-(2-methylphenyl)methylidene-4-methylbenzenesulfonamide 在 C₃₆H₃₆FeN₃PS 、 silver(I) acetate 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 methyl 2-[(diphenylmethylene)amino]-3-(4-methylphenylsulfonamide)-3-(o-methylphenyl)propanoate 、 methyl 2-[(diphenylmethylene)amino]-3-(4-methylphenylsulfonamide)-3-(o-methylphenyl)propanoate
  参考文献：
  名称：

  Ag / ThioClickFerrophos催化的甘氨酸席夫碱的对映选择性曼尼希反应和胺化

  摘要：

  AgOAc / ThioClickFerrophos络合物有效催化甘氨酸席夫碱与N-甲苯磺胺类化合物的不对称曼尼希反应，从而以高收率和高对映选择性（高达90％）合成了顺式和反式加合物的混合物（syn / anti = 60 / 40-70 / 30）。 98％ee）。该配合物还以高对映选择性催化了偶氮二羧酸二叔丁酯对甘氨酸席夫碱的不对称胺化反应。

  DOI：

  10.1021/jo2003727

文献信息

• A<i>N,N′</i>-Dioxide-Copper(II) Complex as an Efficient Catalyst for the Enantioselective and Diastereoselective Mannich-Type Reaction of Glycine Schiff Bases with Aldimines
  作者：Deju Shang、Yanling Liu、Xin Zhou、Xiaohua Liu、Xiaoming Feng

  DOI：10.1002/chem.200900118

  日期：2009.4.6

  A highly diastereo‐ and enantioselective Mannich‐type reaction of glycine Schiff base 1 has been developed by using the N,N′‐dioxide L‐CuII complex as a catalyst. Various optically active anti‐α,β‐diamino acid esters were obtained in good yields with up to 96:4 d.r. and 97 % ee. This straightforward method features a low catalyst loading and mild reaction conditions.

  温和的举止！通过使用N，N'-二氧化物L- Cu II配合物作为催化剂，开发了甘氨酸Schiff碱1的高度非对映和对映选择性曼尼希型反应。以高达96：4 dr和97％ee的高收率获得了各种光学活性的抗α，β-二氨基酸酯 。这种简单的方法具有催化剂负载低和反应条件温和的特点。
• Catalytic Asymmetric Mannich Reaction of Glycine Derivatives with <i>N</i> ‐Tosylimines using Copper(I)/TF‐BiphamPhos Complex
  作者：Gang Liang、Min‐Chao Tong、Haiyan Tao、Chun‐Jiang Wang

  DOI：10.1002/adsc.201000252

  日期：2010.10.9

  The direct asymmetric Mannich reaction of glycine Schiff bases with N-tosylimines has been developed with the tetrakis(acetonitrile)copper(I) tetrafluoroborate [Cu(CH3CN)4BF4]/TF-BiphamPhos complex. This catalytic system performs well over a broad range of substrates, furnishing anti-adducts of various α,β-diamino acid esters in good yields with up to 94:6 diastereoselectivity and 97% enantioselectivity

  用四（乙腈）铜（I）四氟硼酸酯[Cu（CH 3 CN）4 BF 4 ] / TF-BiphamPhos络合物开发了甘氨酸席夫碱与N-甲苯磺酰亚胺的直接不对称曼尼希反应。该催化体系在广泛的底物上表现良好，以高达94：6的非对映选择性和97％的对映选择性提供了各种α，β-二氨基酸酯的抗加合物。
• Synthesis of α,β-diamino acid derivatives via asymmetric Mannich reactions of glycine imino esters catalyzed by a chiral phosphoramidite·silver complex
  作者：Alberto Cayuelas、Loane Serrano、Carmen Nájera、José M. Sansano

  DOI：10.1016/j.tetasy.2014.11.009

  日期：2014.12

  AgOTf phosphoramidite complexes efficiently catalyze the enantioselective Mannich-type reaction between benzophenone-imine glycine methyl ester and N-tosyl aldimines in the absence of a base. The corresponding syn-adducts, which are the direct precursors of alpha,beta-diamino acids, are obtained with moderate to good syn-diastereoselectivities (up to 9:1) and high enantioselectivities (up to 99% ee). (C) 2014 Elsevier Ltd. All rights reserved.