1-phenylhept-6-yn-2-yl 2-diazo-2-(diethoxyphosphoryl)acetate | 1607455-45-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: 1-phenylhept-6-yn-2-yl 2-diazo-2-(diethoxyphosphoryl)acetate
• 英文别名: 1-Phenylhept-6-yn-2-yl 2-diazo-2-[diethoxy(oxido)phosphaniumyl]acetate；1-phenylhept-6-yn-2-yl 2-diazo-2-[diethoxy(oxido)phosphaniumyl]acetate
• CAS: 1607455-45-7
• 化学式: C₁₉H₂₅N₂O₅P
• 分子量: 392.392
• InChiKey: QKUUGFZOQVOCEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  27
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  69.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-phenylhept-6-yn-2-yl 2-diazo-2-(diethoxyphosphoryl)acetate 在 辛酸铑 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成
  参考文献：
  名称：

  A One-Pot C–H Insertion/Olefination Sequence for the Formation of α-Alkylidene-γ-butyrolactones

  摘要：

  A one-pot C-H insertion/olefination sequence for the conversion of alpha-diazo-alpha-(dialkoxyphosphoryl)acetates into alpha-alkylidene-gamma-butyrolactones is reported. The key C-H insertion process is achieved using a catalytic amount of a dirhodium carboxylate catalyst, using operationally simple conditions. The size and electronic properties of the attached substituents were found to influence the regio- and diastereoselectivity of the process. The utility of the process is demonstrated by the synthesis of a known Staphylococcus aureus (MRSA) virulence inhibitor.

  DOI：

  10.1021/ol501092m
• 作为产物：
  描述：

  1-phenylhept-6-yn-2-one 在 1-丙基磷酸酐 、 N,N-二异丙基乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 2.17h， 生成 1-phenylhept-6-yn-2-yl 2-diazo-2-(diethoxyphosphoryl)acetate
  参考文献：
  名称：

  A One-Pot C–H Insertion/Olefination Sequence for the Formation of α-Alkylidene-γ-butyrolactones

  摘要：

  A one-pot C-H insertion/olefination sequence for the conversion of alpha-diazo-alpha-(dialkoxyphosphoryl)acetates into alpha-alkylidene-gamma-butyrolactones is reported. The key C-H insertion process is achieved using a catalytic amount of a dirhodium carboxylate catalyst, using operationally simple conditions. The size and electronic properties of the attached substituents were found to influence the regio- and diastereoselectivity of the process. The utility of the process is demonstrated by the synthesis of a known Staphylococcus aureus (MRSA) virulence inhibitor.

  DOI：

  10.1021/ol501092m

文献信息

• A One-Pot C–H Insertion/Olefination Sequence for the Formation of α-Alkylidene-γ-butyrolactones
  作者：Matthew G. Lloyd、Richard J. K. Taylor、William P. Unsworth

  DOI：10.1021/ol501092m

  日期：2014.5.16

  A one-pot C-H insertion/olefination sequence for the conversion of alpha-diazo-alpha-(dialkoxyphosphoryl)acetates into alpha-alkylidene-gamma-butyrolactones is reported. The key C-H insertion process is achieved using a catalytic amount of a dirhodium carboxylate catalyst, using operationally simple conditions. The size and electronic properties of the attached substituents were found to influence the regio- and diastereoselectivity of the process. The utility of the process is demonstrated by the synthesis of a known Staphylococcus aureus (MRSA) virulence inhibitor.