(3aR,8aR)-4,4,8,8-tetrakis(3,5-dimethylphenyl)-2,2-diethyl-6-phenyltetrahydro[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepine | 1443050-14-3

• 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: (3aR,8aR)-4,4,8,8-tetrakis(3,5-dimethylphenyl)-2,2-diethyl-6-phenyltetrahydro[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepine
• 英文别名: (3aR,8aR)-4,4,8,8-tetrakis(3,5-dimethylphenyl)-2,2-diethyl-6-phenyl-3a,8a-dihydro-[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepine
• CAS: 1443050-14-3
• 化学式: C₄₇H₅₃O₄P
• 分子量: 712.909
• InChiKey: IAMNRQSNEKOTOW-NDOUMJCMSA-N

物化性质

• 沸点：
  736.2±60.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.7
• 重原子数：
  52
• 可旋转键数：
  7
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (4R,5R)-2,2-Diethyl-α,α,α',α'-tetrakis(3,5-dimethylphenyl)-1,3-dioxolane-4,5-dimethanol 、 苯基二氯化磷 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以88%的产率得到(3aR,8aR)-4,4,8,8-tetrakis(3,5-dimethylphenyl)-2,2-diethyl-6-phenyltetrahydro[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepine
  参考文献：
  名称：

  Catalytic Enantioselective One-pot Aminoborylation of Aldehydes: A Strategy for Construction of Nonracemic α-Amino Boronates

  摘要：

  We report a strategy for the conversion of aldehydes to enantiomerically enriched alpha-amino boronates through the intermediacy of in situ-generated silylimines. This transformation is brought about by Pt-catalyzed asymmetric addition of B-2(pin)(2) across the imine double bond. An attractive feature of the intermediate diboration adduct is that it can be acylated directly and provides convenient access to important N-acyl alpha-amino boronic ester derivatives.

  DOI：

  10.1021/ja402569j
• 作为试剂：
  描述：

  3-甲酰基吲哚酸-1-羧酸 t-丁基酯 在 Pt(dba)2 、 (3aR,8aR)-4,4,8,8-tetrakis(3,5-dimethylphenyl)-2,2-diethyl-6-phenyltetrahydro[1,3]dioxolo[4,5-e][1,3,2]dioxaphosphepine 、 三甲基丙酮酸 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 16.83h， 生成 (R)-tert-butyl 3-(pivalamido(4,4,5,5-tetramethyl-1,3,2-di- oxaborolan-2-yl)methyl)-1H-indole-1-carboxylate
  参考文献：
  名称：

  Catalytic Enantioselective One-pot Aminoborylation of Aldehydes: A Strategy for Construction of Nonracemic α-Amino Boronates

  摘要：

  We report a strategy for the conversion of aldehydes to enantiomerically enriched alpha-amino boronates through the intermediacy of in situ-generated silylimines. This transformation is brought about by Pt-catalyzed asymmetric addition of B-2(pin)(2) across the imine double bond. An attractive feature of the intermediate diboration adduct is that it can be acylated directly and provides convenient access to important N-acyl alpha-amino boronic ester derivatives.

  DOI：

  10.1021/ja402569j

文献信息

• Catalytic Enantioselective One-pot Aminoborylation of Aldehydes: A Strategy for Construction of Nonracemic α-Amino Boronates
  作者：Kai Hong、James P. Morken

  DOI：10.1021/ja402569j

  日期：2013.6.26

  We report a strategy for the conversion of aldehydes to enantiomerically enriched alpha-amino boronates through the intermediacy of in situ-generated silylimines. This transformation is brought about by Pt-catalyzed asymmetric addition of B-2(pin)(2) across the imine double bond. An attractive feature of the intermediate diboration adduct is that it can be acylated directly and provides convenient access to important N-acyl alpha-amino boronic ester derivatives.