(S)-2-N-diphenylphosphinoylamino-2-(3-thiophenyl)propionitrile

• 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)-2-N-diphenylphosphinoylamino-2-(3-thiophenyl)propionitrile
• 英文别名: N-[1-cyano-1-(3-thienyl)ethyl]diphenylphosphinic amide；(2S)-2-(diphenylphosphorylamino)-2-thiophen-3-ylpropanenitrile
• 化学式: C₁₉H₁₇N₂OPS
• 分子量: 352.397
• InChiKey: QOQGFWGBPHIPLS-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  81.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  氢氰酸 、 N-(1-thiophen-3-ylethylidene)diphenylphosphinamide 在 gadolinium(III) isopropoxide 、 三甲基氰硅烷 、 1,5-anhydro-2,6-dideoxy-3-O-(4,5-difluoro-2-hydroxyphenyl)-6-(diphenylphosphinyl)-D-arabino-hexitol 作用下， 以 various solvent(s) 为溶剂， 反应 3.0h， 以99%的产率得到(S)-2-N-diphenylphosphinoylamino-2-(3-thiophenyl)propionitrile
  参考文献：
  名称：

  使用催化量的TMSCN和化学计量的HCN催化酮亚胺的对映选择性Strecker反应

  摘要：

  在酮亚胺的对映选择性斯特雷克反应中，催化剂的负载量低至0.1摩尔％。结合使用催化量的TMSCN和化学计算量的HCN作为试剂，以及手性g络合物作为催化剂，可获得出色的对映选择性。

  DOI：

  10.1016/j.tetlet.2004.02.077

文献信息

• Assembly State of Catalytic Modules as Chiral Switches in Asymmetric Strecker Amino Acid Synthesis
  作者：Nobuki Kato、Tsuyoshi Mita、Motomu Kanai、Bruno Therrien、Masaki Kawano、Kentaro Yamaguchi、Hiroshi Danjo、Yoshihisa Sei、Akihiro Sato、Sanae Furusho、Masakatsu Shibasaki

  DOI：10.1021/ja060841r

  日期：2006.5.1

  demonstrate novel properties as asymmetric catalysts. We report the three-dimensional structures of two such asymmetric catalysts (crystals A and B) for Strecker alpha,alpha-disubstituted amino acid synthesis. These complexes are constructed via assembly of the same chiral modules derived from d-glucose, but their assembly modes differ. The enantioselectivity in the Strecker reaction was dramatically switched

  自组装手性多金属配合物通常表现出作为不对称催化剂的新特性。我们报告了用于 Strecker α、α-二取代氨基酸合成的两种这种不对称催化剂（晶体 A 和 B）的三维结构。这些复合物是通过组装来自 d-葡萄糖的相同手性模块构建的，但它们的组装模式不同。Strecker 反应中的对映选择性发生了显着变化，具体取决于使用的组装模式：原位生成的催化剂，其结构由晶体 B 或晶体 A 表示。这些发现提供了对高阶结构的功能重要性的洞察一种人工催化剂。
• Enantioselective Strecker-type reaction of phosphinoyl ketimines catalyzed by a chiral Zr-bipyridyldiol catalyst
  作者：Yi-Jing Chen、Chinpiao Chen

  DOI：10.1016/j.tetasy.2008.09.011

  日期：2008.9

  An enantioselective Strecker reaction of N-diphenylphosphinoyl ketimines with TMSCN employing a chiral zirconium complex formed from chiral bipyridyl diol 1 as catalyst is described. The catalytic efficiency of chiral ligand 1 with other Lewis acids was also explored. Higher yields (50-85%) with moderate to good enantioselectivities (30-80%) were achieved for a variety of N-diphenylphosphinoyl ketimines. (C) 2008 Elsevier Ltd. All rights reserved.
• General and practical catalytic enantioselective Strecker reaction of ketoimines: significant improvement through catalyst tuning by protic additives
  作者：Nobuki Kato、Masato Suzuki、Motomu Kanai、Masakatsu Shibasaki

  DOI：10.1016/j.tetlet.2004.02.082

  日期：2004.4

  Significant improvement in enantioselectivity and catalyst activity was achieved for the catalytic enantio selective Strecker reaction. Using a catalyst (1-2.5 mol%) prepared from Gd((OPr)-Pr-i)(3) and D-glucose derived ligand 1, and in the presence of 2,6-dimethylphenol as an additive, high enantioselectivity was obtained from a wide range of ketoimines, including heteroaromatic and cyclic ketoimines. The new method was applied to an efficient catalytic asymmetric synthesis of sorbinil, a therapeutic agent for diabetic complications. (C) 2004 Elsevier Ltd. All rights reserved.
• Catalytic enantioselective Strecker reaction of ketoimines using catalytic amount of TMSCN and stoichiometric amount of HCN
  作者：Nobuki Kato、Masato Suzuki、Motomu Kanai、Masakatsu Shibasaki

  DOI：10.1016/j.tetlet.2004.02.077

  日期：2004.4

  Catalyst loading as low as 0.1 mol % was achieved in the enantioselective Strecker reaction of ketoimines. Excellent enantioselectivity was obtained with a combined use of a catalytic amount of TMSCN and a stoichiometric amount of HCN as a reagent, and a chiral gadolinium complex as a catalyst.

  在酮亚胺的对映选择性斯特雷克反应中，催化剂的负载量低至0.1摩尔％。结合使用催化量的TMSCN和化学计算量的HCN作为试剂，以及手性g络合物作为催化剂，可获得出色的对映选择性。