(S)-N-trifluoroacetyl-α-allylamino-phenyl-acetonitrile

• 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)-N-trifluoroacetyl-α-allylamino-phenyl-acetonitrile
• 英文别名: N-(cyano(phenyl)methyl)-2,2,2-trifluoro-N-vinylacetamide；(S)-N-allyl-N-(cyano(phenyl)methyl)-2,2,2-trifluoroacetamide；(alphaS)-alpha-[Allyl(trifluoroacetyl)amino]benzeneacetonitrile；N-[(S)-cyano(phenyl)methyl]-2,2,2-trifluoro-N-prop-2-enylacetamide
• 化学式: C₁₃H₁₁F₃N₂O
• 分子量: 268.238
• InChiKey: MGDCWPSRBODTQI-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-(phenylmethylidene)-2-propene-1-amine 在 chiral salicylidene imine derivative 作用下， 以 甲苯 为溶剂， 反应 20.0h， 生成 (S)-N-trifluoroacetyl-α-allylamino-phenyl-acetonitrile
  参考文献：
  名称：

  A General Catalyst for the Asymmetric Strecker Reaction

  摘要：

  DOI：

  10.1002/(sici)1521-3773(20000403)39:7<1279::aid-anie1279>3.0.co;2-u

文献信息

• Highly Enantioselective Titanium-Catalyzed Cyanation of Imines at Room Temperature
  作者：Abdul Majeed Seayad、Balamurugan Ramalingam、Kazuhiko Yoshinaga、Takushi Nagata、Christina L. L. Chai

  DOI：10.1021/ol902540h

  日期：2010.1.15

  A highly active and enantioselective titanium-catalyzed cyanation of imines at room temperature is described. The catalyst used is a partially hydrolyzed titanium alkoxide (PHTA) precatalyst together with a readily available N-salicyl-β-aminoalcohol ligand. Up to 98% ee was obtained with quantitative yields in 15 min of reaction time using 5 mol % of the catalyst. Various N-protecting groups such as

  描述了在室温下高活性和对映选择性的钛催化的亚胺氰化。所用的催化剂是部分水解的烷氧基钛（PHTA）预催化剂以及易于获得的N-水杨基-β-氨基醇配体。使用5 mol％的催化剂，在15分钟的反应时间内以定量收率获得了高达98％ee。可以耐受各种N保护基，例如苄基，苯甲基，Boc和PMP。
• HCN on Tap: On-Demand Continuous Production of Anhydrous HCN for Organic Synthesis
  作者：Manuel Köckinger、Christopher A. Hone、C. Oliver Kappe

  DOI：10.1021/acs.orglett.9b01941

  日期：2019.7.5

  technology was developed. The inner tube of the reactor is manufactured from a gas-permeable, hydrophobic fluoropolymer (Teflon AF-2400) membrane. HCN is formed from aqueous reagents within the inner tube and then diffuses through the membrane into an outer tubing containing organic solvent. This technique enabled the safe handling of HCN for three different organic transformations without the need for distillation

  开发了一种使用膜分离技术按需生成，分离和反应氰化氢（HCN）的连续方法。反应器的内管由透气的疏水性含氟聚合物（Teflon AF-2400）膜制成。HCN由内管内的水性试剂形成，然后通过膜扩散到含有有机溶剂的外管中。该技术无需蒸馏即可安全处理三种不同的有机转化形式的六氯化萘。
• Enantioselective Organocatalysis of Strecker and Mannich Reactions Based on Carbohydrates
  作者：Christian Becker、Christine Hoben、Horst Kunz

  DOI：10.1002/adsc.200600370

  日期：2007.2.5

  Efficient organocatalysts for enantioselective Strecker and Mannich reactions were constructed from glucosamine as a readily accessible chiral scaffold. A variety of aromatic aldimines were subjected to hydrocyanation with good to excellent yield (72–98 %) and, in part, high enantioselectivity (69–95 % ee). Influence of the catalyst architecture on the enantioselectivity obviously arises from restrictions

  对映选择性Strecker和Mannich反应的有效有机催化剂是由氨基葡萄糖构建的，它是一种易于获得的手性支架。各种芳香醛亚胺都进行了氢氰化，收率良好至优异（72％至98％），部分对映选择性高（ee值为69％至95％）。催化剂结构对对映选择性的影响显然是由于对单糖主链的构象柔韧性施加了限制。在不对称曼尼希反应中，使用所述催化剂已经获得了中等产率（高达76％）和对映选择性（高达58％ee）。
• Divergent Stereoinduction Mechanisms in Urea-Catalyzed Additions to Imines
  作者：Eric N. Jacobsen、Anna G. Wenzel、Mathieu P. Lalonde

  DOI：10.1055/s-2003-41503

  日期：——

  Catalyst structure/enantioselectivity profiles for the asymmetric Strecker and Mannich reactions were obtained through systematic variation of each modular component of the catalyst. Althoug­h the thiourea derivative 1 afforded optimal results in both reactions (97-98% ee), the structural elements responsible for stereo­induction were found to be fundamentally different. Insights gleaned from these studies led to the development of a new generatio­n catalyst for the Mannich reaction that promotes the asymmetric silyl ketene acetal addition to N-Boc benzaldimine in 94% ee. The new catalyst is a simple amino acid derivative possesses­ing less than half the molecular weight and two fewer stereo­centers relative to 1.

  通过系统地改变催化剂的每个模块成分，获得了不对称 Strecker 反应和 Mannich 反应的催化剂结构/对映体选择性曲线。虽然硫脲衍生物 1 在这两个反应中都能提供最佳结果（97-98% ee），但发现负责立体诱导的结构元素存在本质区别。从这些研究中获得的启示促成了新一代曼尼希反应催化剂的开发，该催化剂可促进 N-Boc 苯甲醛二胺的不对称硅酮缩醛加成反应，ee 值高达 94%。这种新型催化剂是一种简单的氨基酸衍生物，其分子量不到 1 的一半，立体中心也比 1 少两个。
• A New Chiral Catalyst for the Enantioselective Strecker Synthesis of α-Amino Acids
  作者：Jinkun Huang、E. J. Corey

  DOI：10.1021/ol047698w

  日期：2004.12.1

  The chiral ammonium salt 3 is demonstrated to be an effective catalyst for the highly enantioselective Strecker reaction of N-allylbenzaldimines with hydrogen cyanide in CH2Cl2 solution.