[3-[(2-Chloroacetyl)amino]-1-hydroxy-1-phosphonopropyl]phosphonic acid | 1254836-01-5

• 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: [3-[(2-Chloroacetyl)amino]-1-hydroxy-1-phosphonopropyl]phosphonic acid
• 英文别名: [3-[(2-chloroacetyl)amino]-1-hydroxy-1-phosphonopropyl]phosphonic acid
• CAS: 1254836-01-5
• 化学式: C₅H₁₂ClNO₈P₂
• 分子量: 311.553
• InChiKey: GDPLJWXOPSHEOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.7
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  176
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  帕米膦酸 、 氯乙酰氯 在 sodium hydroxide 、 盐酸 作用下， 以 水 为溶剂， 反应 6.0h， 以37%的产率得到[3-[(2-Chloroacetyl)amino]-1-hydroxy-1-phosphonopropyl]phosphonic acid
  参考文献：
  名称：

  Fragmentation pathways of eight nitrogen-containing bisphosphonates (BPs) investigated by ESI-MSn in negative ion mode

  摘要：

  Fragmentation pathways of eight nitrogen-containing bisphosphonates (BPs), including Pamidronate, Alendronate, and five corresponding acylated derivatives, and Risedronate, were investigated by electro-spray ionization mass spectrometry (ESI-MS) in conjunction with tandem mass spectrometry in negative ion mode. Characteristic fragment ions involved were formed by successive loss of water molecules, including alpha, beta-unsaturated product ions formed by dehydration of the alpha-hydroxyl group and beta-hydrogen, cyclic ions with P-O-P four-membered rings formed by dehydration of the two -OH groups attached to two phosphorus atoms, and cyclic phosphoramide ions with five- or six-membered rings formed by loss of water via an intramolecular nucleophilic substitution reaction, in which -NH2 (or -NH-) group on gamma or 8 carbon acted as the nucleophile to attack phosphorus atom of P=O group at the initial stage. Another notable characteristic product ion [HP2O5](-) at m/z 143, shown by all eight ESL-MS2 spectra, is a diagnostic ion of bisphosphonate group, formed from the four-membered ring ion containing P-O-P. Some additional fragmentation ions were produced from chloroacetyl Alendronate, chloroacetyl Pamidronate, and Risedronate containing triple bond ions, formed by loss of water from the corresponding enol anions. The hydrogen/deuterium (H/D) exchange experiment, theoretical calculations, and the high-resolution mass spectrometry were appropriately employed to rationalize the proposed fragmentation pathways. Crown Copyright (C) 2010 Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ijms.2010.07.017

文献信息

• Fragmentation pathways of eight nitrogen-containing bisphosphonates (BPs) investigated by ESI-MSn in negative ion mode
  作者：Zhibo Qu、Xiaolan Chen、Chen Qu、Lingbo Qu、Jinwei Yuan、Donghui Wei、Huina Li、Xiaoying Huang、Yuqin Jiang、Yufen Zhao

  DOI：10.1016/j.ijms.2010.07.017

  日期：2010.7

  Fragmentation pathways of eight nitrogen-containing bisphosphonates (BPs), including Pamidronate, Alendronate, and five corresponding acylated derivatives, and Risedronate, were investigated by electro-spray ionization mass spectrometry (ESI-MS) in conjunction with tandem mass spectrometry in negative ion mode. Characteristic fragment ions involved were formed by successive loss of water molecules, including alpha, beta-unsaturated product ions formed by dehydration of the alpha-hydroxyl group and beta-hydrogen, cyclic ions with P-O-P four-membered rings formed by dehydration of the two -OH groups attached to two phosphorus atoms, and cyclic phosphoramide ions with five- or six-membered rings formed by loss of water via an intramolecular nucleophilic substitution reaction, in which -NH2 (or -NH-) group on gamma or 8 carbon acted as the nucleophile to attack phosphorus atom of P=O group at the initial stage. Another notable characteristic product ion [HP2O5](-) at m/z 143, shown by all eight ESL-MS2 spectra, is a diagnostic ion of bisphosphonate group, formed from the four-membered ring ion containing P-O-P. Some additional fragmentation ions were produced from chloroacetyl Alendronate, chloroacetyl Pamidronate, and Risedronate containing triple bond ions, formed by loss of water from the corresponding enol anions. The hydrogen/deuterium (H/D) exchange experiment, theoretical calculations, and the high-resolution mass spectrometry were appropriately employed to rationalize the proposed fragmentation pathways. Crown Copyright (C) 2010 Published by Elsevier B.V. All rights reserved.