methylenebisphosphonic acid P,P'-dicyclohexyl diester | 23501-59-9

• 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: methylenebisphosphonic acid P,P'-dicyclohexyl diester
• 英文别名: P,P'-dicyclohexylhexyl methylenebisphosphonic acid；Bis--methan；Bis-(hydroxy-cyclohexyloxy-phosphinoyl)-methan；Cyclohexyloxy-[[cyclohexyloxy(hydroxy)phosphoryl]methyl]phosphinic acid
• CAS: 23501-59-9
• 化学式: C₁₃H₂₆O₆P₂
• 分子量: 340.293
• InChiKey: KDNARRBCQYTGGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  methylenebis(cyclohexyl methyl phosphonate) 在 三甲基溴硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以94%的产率得到methylenebisphosphonic acid P,P'-dicyclohexyl diester
  参考文献：
  名称：

  Facile high yielding synthesis of symmetric esters of methylenebisphosphonic acid

  摘要：

  The 1H-tetrazole catalyzed coupling of methylenebis(phosphonic dichloride), CH2(POCl2)(2), with primary alkyl, cyclic secondary alkyl, aromatic, and silicon- and fluorine-containing alcohols selectively affords symmetric P,P'-dialkyl partial esters as wen as homoleptic and mixed tetraesters. Two partial ester intermediates, methylenebis(2-ethylhexyl phosphonic chloride) and 2-ethylhexyl methylenebisphosphonic trichloride, were observed by H-1- and P-31 NMR spectroscopy in the esterification of CH2(POCl2)(2) with 2-ethyl-1-hexanol. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00846-8

文献信息

• A FACILE AND SELECTIVE HIGH YIELD SYNTHESIS OF SYMMETRIC DIALKYL-SUBSTITUTED METHYLENEBISPHOSPHONIC ACIDS
  作者：Dominique C. Stepinski、Albert W. Herlinger

  DOI：10.1081/scc-120006033

  日期：2002.1

  ABSTRACT Symmetric P,P′-dialkyl partial esters of methylenebisphosphonic acid were prepared in high yield and high selectivity from the corresponding acid chloride via a facile two-step, one-pot process. The newly developed synthesis, which does not require chromatographic or acid–base extractive purification, offers substantial advantages over previously used procedures.

  摘要 通过简便的两步一锅法从相应的酰氯以高收率和高选择性制备亚甲基双膦酸的对称 P,P'-二烷基偏酯。新开发的合成不需要色谱或酸碱萃取纯化，与以前使用的程序相比具有很大的优势。
• Facile high yielding synthesis of symmetric esters of methylenebisphosphonic acid
  作者：Dominique C Stepinski、Derek W Nelson、Peter R Zalupski、Albert W Herlinger

  DOI：10.1016/s0040-4020(01)00846-8

  日期：2001.10

  The 1H-tetrazole catalyzed coupling of methylenebis(phosphonic dichloride), CH2(POCl2)(2), with primary alkyl, cyclic secondary alkyl, aromatic, and silicon- and fluorine-containing alcohols selectively affords symmetric P,P'-dialkyl partial esters as wen as homoleptic and mixed tetraesters. Two partial ester intermediates, methylenebis(2-ethylhexyl phosphonic chloride) and 2-ethylhexyl methylenebisphosphonic trichloride, were observed by H-1- and P-31 NMR spectroscopy in the esterification of CH2(POCl2)(2) with 2-ethyl-1-hexanol. (C) 2001 Elsevier Science Ltd. All rights reserved.