(4S)-4-(diphenylphosphorylamino)-6-fluoro-2,3-dihydrochromene-4-carbonitrile | 692754-62-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (4S)-4-(diphenylphosphorylamino)-6-fluoro-2,3-dihydrochromene-4-carbonitrile
• CAS: 692754-62-4
• 化学式: C₂₂H₁₈FN₂O₂P
• 分子量: 392.369
• InChiKey: ANHUYRBNRDCCFN-JOCHJYFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  62.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4S)-4-(diphenylphosphorylamino)-6-fluoro-2,3-dihydrochromene-4-carbonitrile 在 盐酸 作用下， 以 水 为溶剂， 反应 38.0h， 生成 索比尼尔
  参考文献：
  名称：

  General and practical catalytic enantioselective Strecker reaction of ketoimines: significant improvement through catalyst tuning by protic additives

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2004.02.082
• 作为产物：
  描述：

  三甲基氰硅烷 、 (E)-N-diphenylphosphoryl-6-fluoro-2,3-dihydrochromen-4-imine 在 gadolinium(III) isopropoxide 、 2,6-二甲基苯酚 、 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 83.0h， 以93%的产率得到(4S)-4-(diphenylphosphorylamino)-6-fluoro-2,3-dihydrochromene-4-carbonitrile
  参考文献：
  名称：

  General and practical catalytic enantioselective Strecker reaction of ketoimines: significant improvement through catalyst tuning by protic additives

  摘要：

  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.

  DOI：

  10.1016/j.tetlet.2004.02.082

文献信息

• 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。
• 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.