{[Butyl-(2-methoxy-ethyl)-carbamoyl]-diazo-methyl}-phosphonic acid diethyl ester | 906125-48-2

• 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: {[Butyl-(2-methoxy-ethyl)-carbamoyl]-diazo-methyl}-phosphonic acid diethyl ester
• 英文别名: N-butyl-2-diazo-2-diethoxyphosphoryl-N-(2-methoxyethyl)acetamide
• CAS: 906125-48-2
• 化学式: C₁₃H₂₆N₃O₅P
• 分子量: 335.34
• InChiKey: NSKKVUCSRMVYOO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  22
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  67.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  {[Butyl-(2-methoxy-ethyl)-carbamoyl]-diazo-methyl}-phosphonic acid diethyl ester 在 dirhodium tetraacetate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 3.0h， 生成 [(3R,4S)-4-Ethyl-1-(2-methoxy-ethyl)-2-oxo-pyrrolidin-3-yl]-phosphonic acid diethyl ester 、 ((3R,4S)-1-Butyl-4-methoxy-2-oxo-pyrrolidin-3-yl)-phosphonic acid diethyl ester
  参考文献：
  名称：

  Rh(II)-Catalyzed Intramolecular C−H Insertion of Diazo Substrates in Water:  Scope and Limitations

  摘要：

  Preferential Rh(II) carbenoid intramolecular C-H versus O-H insertion derived from R-diazo-acetamides can be achieved in water by using an appropriate combination of the catalyst and amide groups, which creates a larger hydrophobic environment around the reactive carbenoid center.

  DOI：

  10.1021/jo060397a
• 作为产物：
  描述：

  N-(n-butyl)-N-(2-methoxyethyl)amine 在 对甲苯磺酰叠氮 、 sodium hydride 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 {[Butyl-(2-methoxy-ethyl)-carbamoyl]-diazo-methyl}-phosphonic acid diethyl ester
  参考文献：
  名称：

  Rh(II)-Catalyzed Intramolecular C−H Insertion of Diazo Substrates in Water:  Scope and Limitations

  摘要：

  Preferential Rh(II) carbenoid intramolecular C-H versus O-H insertion derived from R-diazo-acetamides can be achieved in water by using an appropriate combination of the catalyst and amide groups, which creates a larger hydrophobic environment around the reactive carbenoid center.

  DOI：

  10.1021/jo060397a

文献信息

• Rh(II)-Catalyzed Intramolecular C−H Insertion of Diazo Substrates in Water:  Scope and Limitations
  作者：Nuno R. Candeias、Pedro M. P. Gois、Carlos A. M. Afonso

  DOI：10.1021/jo060397a

  日期：2006.7.1

  Preferential Rh(II) carbenoid intramolecular C-H versus O-H insertion derived from R-diazo-acetamides can be achieved in water by using an appropriate combination of the catalyst and amide groups, which creates a larger hydrophobic environment around the reactive carbenoid center.