(2S)-N,2-dibenzyl-3,3,3-trifluoropropan-1-amine | 1180131-23-0

• 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: (2S)-N,2-dibenzyl-3,3,3-trifluoropropan-1-amine
• CAS: 1180131-23-0
• 化学式: C₁₇H₁₈F₃N
• 分子量: 293.332
• InChiKey: CDWVPUSHEKMPGN-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯丙醛 在 2,6-二甲基吡啶 、 Ir(ppy)2(dtb-bpy)PF₆ 、 (2R,5S)-2-(tert-butyl)-3,5-dimethylimidazolidin-4-one trifluoroacetate 、 sodium cyanoborohydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.5h， 生成 (2S)-N,2-dibenzyl-3,3,3-trifluoropropan-1-amine 、
  参考文献：
  名称：

  Enantioselective α-Trifluoromethylation of Aldehydes via Photoredox Organocatalysis

  摘要：

  The first enantioselective, organocatalytic alpha-trifluoromethytation and alpha-perfluoroalkylation of aldehydes have been accomplished using a readily available iridium photocatalyst and a chiral imidazolidinone catalyst. A range of alpha-trifluoromethyl and alpha-perfluoroalkyl aldehydes were obtained from commercially available perfluoroalkyl halides with high efficiency and enantioselectivity. The resulting alpha-trifluoromethyl aldehydes were subsequently shown to be versatile precursors for the construction of a variety of enantioenriched trifluoromethylated building blocks.

  DOI：

  10.1021/ja9053338

文献信息

• Enantioselective Organocatalytic Reduction of β-Trifluoromethyl Nitroalkenes: An Efficient Strategy for the Synthesis of Chiral β-Trifluoromethyl Amines
  作者：Elisabetta Massolo、Maurizio Benaglia、Manuel Orlandi、Sergio Rossi、Giuseppe Celentano

  DOI：10.1002/chem.201405730

  日期：2015.2.23

  β‐trifluoromethyl‐substituted nitroalkenes, mediated by 3,5‐dicarboxylic ester‐dihydropyridines (Hantzsch ester type), has been successfully developed. A multifunctional thiourea‐based (S)‐valine derivative was found to be the catalyst of choice, promoting the reaction in up to 97 % ee. The methodology has been applied to a wide variety of substrates, leading to the formation of differently substituted precursors

  已经成功开发了由3,5-二羧酸酯-二氢吡啶（Hantzsch酯型）介导的有效的有机催化立体选择性还原β-三氟甲基取代的硝基烯烃。发现多功能硫脲基（S）-缬氨酸衍生物是选择的催化剂，可促进高达97％ee的反应 。该方法已应用于多种底物，导致形成对映体富集的β-三氟甲基胺的不同取代的前体。通过计算研究了无金属催化物质的反应机理和作用方式。在DFT过渡态（TS）分析的基础上，还提出了立体选择模型。
• The Productive Merger of Iodonium Salts and Organocatalysis: A Non-photolytic Approach to the Enantioselective α-Trifluoromethylation of Aldehydes
  作者：Anna E. Allen、David W. C. MacMillan

  DOI：10.1021/ja100748y

  日期：2010.4.14

  An enantioselective organocatalytic alpha-trifluoromethylation of aldehydes has been accomplished using a commercially available, electrophilic trifluoromethyl source. The merging of Lewis acid and organocatalysis provides a new strategy for the enantioselective construction of trifluoromethyl stereogenicity, an important chiral synthon for pharmaceutical, materials, and agrochemical applications. This mild and operationally simple protocol allows rapid access to enantioenriched alpha-trifluoromethylated aldehydes through a nonphotolytic pathway.
• Enantioselective α-Trifluoromethylation of Aldehydes via Photoredox Organocatalysis
  作者：David A. Nagib、Mark E. Scott、David W. C. MacMillan

  DOI：10.1021/ja9053338

  日期：2009.8.12

  The first enantioselective, organocatalytic alpha-trifluoromethytation and alpha-perfluoroalkylation of aldehydes have been accomplished using a readily available iridium photocatalyst and a chiral imidazolidinone catalyst. A range of alpha-trifluoromethyl and alpha-perfluoroalkyl aldehydes were obtained from commercially available perfluoroalkyl halides with high efficiency and enantioselectivity. The resulting alpha-trifluoromethyl aldehydes were subsequently shown to be versatile precursors for the construction of a variety of enantioenriched trifluoromethylated building blocks.