(2S,3R)-tert-butyl 3-(4-bromophenyl)-3-((tertbutoxycarbonyl)amino)-2-((diphenylmethylene)amino)propanoate | 1431529-41-7

• 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: (2S,3R)-tert-butyl 3-(4-bromophenyl)-3-((tertbutoxycarbonyl)amino)-2-((diphenylmethylene)amino)propanoate
• 英文别名: tert-butyl (2S,3R)-2-(benzhydrylideneamino)-3-(4-bromophenyl)-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 1431529-41-7
• 化学式: C₃₁H₃₅BrN₂O₄
• 分子量: 579.534
• InChiKey: AAJPHDJLTOGJSJ-SXOMAYOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  77
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  tert-butyl 4-bromobenzylidenecarbamate 、 N-二苯亚甲基-甘氨酸叔丁酯 在 (2R,4R,8S)-1-((2,2'-bis(anthracen-9-ylmethoxy)-1,1'-binaphthyl-3-yl)methyl)-2-((S)-hydroxy(6-methoxyquinolin-4-yl)methyl)-8-vinyl-1-azoniabicyclo[2.2.2]octane bromide 、 caesium carbonate 、 sodium sulfate 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以90%的产率得到(2S,3R)-tert-butyl 3-(4-bromophenyl)-3-((tertbutoxycarbonyl)amino)-2-((diphenylmethylene)amino)propanoate
  参考文献：
  名称：

  鸡胆碱盐催化的甘氨酸席夫碱的高度对映选择性曼尼希型反应

  摘要：

  源自金鸡纳生物碱骨架和BINOL骨架的手性相转移催化剂，使甘氨酸Schiff碱与N-Boc-亚胺进行曼尼希反应，能够以极高的收率（高达99％）生成α，β-二氨基酸衍生物）和非对映异构体和对映异构体具有很高的选择性（高达> 20：1 dr，96％ee）。

  DOI：

  10.1002/cjoc.201400453

文献信息

• [EN] CYCLOPROPENIMINE CATALYST COMPOSITIONS AND PROCESSES<br/>[FR] COMPOSITIONS CATALYTIQUES À BASE DE CYCLOPROPÉNIMINE ET PROCÉDÉS
  申请人：UNIV COLUMBIA

  公开号：WO2013059118A1

  公开（公告）日：2013-04-25

  The present invention provides, inter alia, a cyclopropenimine Brønsted base catalyst and a cyclopropenimine scaffold for use as a Brønsted base catalyst. This cyclopropenimine has the structure (100). Methods for making such a cyclopropenimine are also provided. Further provided are processes for carrying out an organic synthetic reaction and processes for catalyzing a proton transfer reaction enantioselectively using such a cyclopropenimine Brønsted base catalyst.

  本发明提供了环丙烯亚胺Brønsted碱催化剂和用作Brønsted碱催化剂的环丙烯亚胺骨架，其中该环丙烯亚胺具有结构（100）。还提供了制备这种环丙烯亚胺的方法。此外，还提供了进行有机合成反应的方法以及利用这种环丙烯亚胺Brønsted碱催化剂对质子转移反应进行对映选择性催化的方法。
• Cyclopropenimine-Catalyzed Enantioselective Mannich Reactions of <i>tert</i>-Butyl Glycinates with <i>N</i>-Boc-Imines
  作者：Jeffrey S. Bandar、Tristan H. Lambert

  DOI：10.1021/ja407277a

  日期：2013.8.14

  shown to catalyze Mannich reactions between glycine imines and N-Boc-aldimines with high levels of enantio- and diastereocontrol. The reactivity of 1 is shown to be substantially greater than that of a widely used thiourea cinchona alkaloid-derived catalyst. A variety of aryl and aliphatic N-Boc-aldimines are effective substrates for this transformation. A preparative-scale reaction to deliver >90 mmol

  Cyclopropenimine 1 显示出催化甘氨酸亚胺和 N-Boc-醛亚胺之间的曼尼希反应，具有高水平的对映和非对映控制。显示 1 的反应性大大高于广泛使用的硫脲金鸡纳生物碱衍生催化剂的反应性。各种芳基和脂肪族 N-Boc-醛亚胺是这种转化的有效底物。显示了使用 1 mol% 催化剂产生 >90 mmol 产物的制备级反应。这种转化的产物可以转化为几种有用的衍生物。
• A novel quaternary ammonium salts derived from α-amino acids with large steric hindrance group and its application in asymmetric Mannich reaction
  作者：Zhengtao Tian、Xiangyu Meng、Yueyang Luo、Shaokui Cao、Gang Zhao

  DOI：10.1016/j.tet.2020.131484

  日期：2020.9

  Quaternary ammonium salts derived from amino acids with large steric hindrance group have been designed and synthesized, which promoted the asymmetric Mannich reaction of glycine imines with N-Boc-aldimines in excellent yields with high enantio- and diastereo-control compared with known catalysts of this type reported by our group.

  设计并合成了具有大空间位阻基团的氨基酸衍生的季铵盐，与已知的催化剂相比，它促进了甘氨酸亚胺与N -Boc-醛亚胺的不对称曼尼希反应，收率高，对映体和非对映体控制率高我们小组报告的类型。
• CYCLOPROPENIMINE CATALYST COMPOSITIONS AND PROCESSES
  申请人：THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK

  公开号：US20140288323A1

  公开（公告）日：2014-09-25

  The present invention provides, inter alia, a cyclopropenimine Brønsted base catalyst and a cyclopropenimine scaffold for use as a Brønsted base catalyst. This cyclopropenimine has the structure (100). Methods for making such a cyclopropenimine are also provided. Further provided are processes for carrying out an organic synthetic reaction and processes for catalyzing a proton transfer reaction enantioselectively using such a cyclopropenimine Brønsted base catalyst.