methyl (4-nitrobenzyl)phosphonochloridate | 167700-91-6

• 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: methyl (4-nitrobenzyl)phosphonochloridate
• 英文别名: Methyl [(4-nitrophenyl)methyl]phosphonochloridate；1-[[chloro(methoxy)phosphoryl]methyl]-4-nitrobenzene
• CAS: 167700-91-6
• 化学式: C₈H₉ClNO₄P
• 分子量: 249.591
• InChiKey: SYTIGHYCIOAIOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (4-nitrobenzyl)phosphonochloridate 、 N-(benzylglutaryl)-4-hydroxypiperidine 在 lithium diisopropyl amide 作用下， 生成 N-(benzylglutaryl)-4-((methoxy(4-nitrobenzyl)phosphinyl)oxy)piperidine
  参考文献：
  名称：

  The Potential Application of Catalytic Antibodies to Protecting Group Removal: Catalytic Antibodies with Broad Substrate Tolerance

  摘要：

  A catalytic antibody was developed to selectively cleave the alcohol ester of 4-nitrophenylacetyl moiety while also tolerating a wide variety of structural variation on the alcohol portion of the molecule. The basis to the success of this study was that antibody epitope recognition was directed toward only key elements contained within the 4-nitrophenylacetyl group and not the entire haptenic molecule. This study offers the potential application of catalytic antibodies as practical reagents for the selective deprotection of complex multifunctionalized molecules possessing class similar protecting groups. Such a chemoabzymatic approach could eventually minimize synthetic complications which can arise from functional group protection in the synthesis of complex natural products.

  DOI：

  10.1021/ja00113a001
• 作为产物：
  描述：

  dimethyl (4-nitrobenzyl)phosphonate 在 五氯化磷 作用下， 以 氯仿 为溶剂， 反应 3.0h， 生成 methyl (4-nitrobenzyl)phosphonochloridate
  参考文献：
  名称：

  The Potential Application of Catalytic Antibodies to Protecting Group Removal: Catalytic Antibodies with Broad Substrate Tolerance

  摘要：

  A catalytic antibody was developed to selectively cleave the alcohol ester of 4-nitrophenylacetyl moiety while also tolerating a wide variety of structural variation on the alcohol portion of the molecule. The basis to the success of this study was that antibody epitope recognition was directed toward only key elements contained within the 4-nitrophenylacetyl group and not the entire haptenic molecule. This study offers the potential application of catalytic antibodies as practical reagents for the selective deprotection of complex multifunctionalized molecules possessing class similar protecting groups. Such a chemoabzymatic approach could eventually minimize synthetic complications which can arise from functional group protection in the synthesis of complex natural products.

  DOI：

  10.1021/ja00113a001

文献信息

• The Potential Application of Catalytic Antibodies to Protecting Group Removal: Catalytic Antibodies with Broad Substrate Tolerance
  作者：Tingyu Li、Susan Hilton、Kim D. Janda

  DOI：10.1021/ja00113a001

  日期：1995.3

  A catalytic antibody was developed to selectively cleave the alcohol ester of 4-nitrophenylacetyl moiety while also tolerating a wide variety of structural variation on the alcohol portion of the molecule. The basis to the success of this study was that antibody epitope recognition was directed toward only key elements contained within the 4-nitrophenylacetyl group and not the entire haptenic molecule. This study offers the potential application of catalytic antibodies as practical reagents for the selective deprotection of complex multifunctionalized molecules possessing class similar protecting groups. Such a chemoabzymatic approach could eventually minimize synthetic complications which can arise from functional group protection in the synthesis of complex natural products.