N-(1,2,2-trimethylpropylidene)diphenylphosphinamide | 945547-09-1

• 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: N-(1,2,2-trimethylpropylidene)diphenylphosphinamide
• 英文别名: N-[(E)-1,2,2-trimethylpropylidene]-P,P-diphenylphosphinic amide；(E)-N-diphenylphosphoryl-3,3-dimethylbutan-2-imine
• CAS: 945547-09-1
• 化学式: C₁₈H₂₂NOP
• 分子量: 299.353
• InChiKey: ZLPJPSAGYLCQPR-XDJHFCHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  29.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(1,2,2-trimethylpropylidene)diphenylphosphinamide 在 potassium fluoride 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以62%的产率得到3-t-butyl-3-methyl-2-(diphenylphosphinoyl)oxaziridine
  参考文献：
  名称：

  trans-(±)-2-tert-Butyl-3-phenyloxaziridine:  A Unique Reagent for the Oxidation of Thiolates into Sulfenates

  摘要：

  Aliphatic thiolates were efficiently converted into the corresponding sulfenates by smooth oxidation with trans-(+/-)-2-tert-butyl-3-phenyloxaziridine at room temperature (five examples). Subsequent electrophilic quench with benzyl bromide led to sulfoxides (S-alkylation) in good to moderate yields. Application of the protocol to an aromatic substrate was also successful. This work represents the first valuable example of the use of this poorly active oxidizing agent in synthetic organic chemistry without the need for activating conditions.

  DOI：

  10.1021/jo070700n
• 作为产物：
  描述：

  频哪酮 在 盐酸羟胺 、 sodium acetate 、 三乙胺 作用下， 以 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 20.0h， 生成 N-(1,2,2-trimethylpropylidene)diphenylphosphinamide
  参考文献：
  名称：

  trans-(±)-2-tert-Butyl-3-phenyloxaziridine:  A Unique Reagent for the Oxidation of Thiolates into Sulfenates

  摘要：

  Aliphatic thiolates were efficiently converted into the corresponding sulfenates by smooth oxidation with trans-(+/-)-2-tert-butyl-3-phenyloxaziridine at room temperature (five examples). Subsequent electrophilic quench with benzyl bromide led to sulfoxides (S-alkylation) in good to moderate yields. Application of the protocol to an aromatic substrate was also successful. This work represents the first valuable example of the use of this poorly active oxidizing agent in synthetic organic chemistry without the need for activating conditions.

  DOI：

  10.1021/jo070700n

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。