methylenebis(2-ethylhexyl methyl phosphonate)

• 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: methylenebis(2-ethylhexyl methyl phosphonate)
• 英文别名: 3-[[[2-Ethylhexoxy(methoxy)phosphoryl]methyl-methoxyphosphoryl]oxymethyl]heptane
• 化学式: C₁₉H₄₂O₆P₂
• 分子量: 428.486
• InChiKey: LJVQQCOPAMWOSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  27
• 可旋转键数：
  18
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methylenebis(2-ethylhexyl methyl phosphonate) 在 吗啉 作用下， 以64%的产率得到methylenebisphosphonic acid P,P'-di(2-ethylhexyl) diester
  参考文献：
  名称：

  用吗啉选择性裂解亚甲基双（二烷基膦酸酯）合成对称亚甲基双（烷基氢膦酸酯）

  摘要：

  摘要 由于其潜在的治疗应用，亚甲基双膦酸偏酯的制备最近引起了人们的兴趣。本文描述了一种通过用回流的吗啉选择性裂解相应的亚甲基双（二烷基膦酸）来制备对称亚甲基双（烷基氢膦酸）的简便方法。已经研究了结构变化对胺和底物的影响，以了解该反应的范围和局限性。受阻双膦酸酯的一种更好的方法是使用吗啉裂解它们的二甲酯 4。该方法也可用于获取许多 C-烷基二烷基亚甲基双膦酸，例如 6。该研究清楚地表明，用吗啉裂解方便、便宜、

  DOI：

  10.1081/scc-120027271
• 作为产物：
  描述：

  亚甲基双膦酰二氯 、 甲醇 、 2-乙基己醇 在 四氮唑 、 N,N-二异丙基乙胺 作用下， 以 甲苯 为溶剂， 反应 0.25h， 以82%的产率得到methylenebis(2-ethylhexyl methyl phosphonate)
  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

• Facile synthesis of symmetric esters of alkylenebisphosphonic acids
  申请人：——

  公开号：US20030060648A1

  公开（公告）日：2003-03-27

  A facile synthesis of symmetric esters of C 1 -C 10 alkylenebisphopsphonic acids is disclosed in which a C 1 -C 10 alkylenebis(phosphonic dichloride) is reacted with an alcohol in the presence of a catalytic amount of 1H-tetrazole and a base in an aprotic solvent to form a first reaction mixture. The first reaction mixture is maintained for a time period sufficient to form a C 1 -C 10 alkylenebis(chloro ester phosphonate) that is reacted under basic conditions with an excess of a hydroxylated compound to form a second reaction mixture that is itself maintained for a time period sufficient to form a C 1 -C 10 alkylenebis(ester phosphonate) partial ester, homoleptic tetraester or mixed tetraester. The material so formed can be recovered or used as is.

  本文披露了一种对称的C1-C10烷基双膦酸酯的简便合成方法，其中C1-C10烷基双(膦酸二氯化物)与醇在无极性溶剂中，在1H-四唑催化剂和碱的存在下反应形成第一反应混合物。第一反应混合物维持一定时间，形成C1-C10烷基双(氯酯膦酸酯)，在碱性条件下与过量的羟基化合物反应形成第二反应混合物，第二反应混合物维持一定时间，形成C1-C10烷基双(酯膦酸酯)部分酯、同配体四酯或混合四酯。所形成的材料可以回收或直接使用。
• US6909010B2
  申请人：——

  公开号：US6909010B2

  公开（公告）日：2005-06-21
• [EN] A FACILE SYNTHESIS OF SYMMETRIC ESTERS OF ALKYLENEBISPHOSPHONIC ACIDS<br/>[FR] SYNTHESE FACILE D'ESTERS SYMETRIQUES D'ACIDES D'ALCOYLENE BISPHOSPHONIQUES
  申请人：UNIV LOYOLA CHICAGO

  公开号：WO2002085918A1

  公开（公告）日：2002-10-31

  A facile synthesis of symmetric esters of C1-C10 alkylenebisphopshonic acids is disclosed in which a C1-C10 alkylenebis(phosphonic dichloride) is reacted with an alcohol in the presence of a catalytic amount of 1H-tetrazole and a base in an apro tic solvent to form a first reaction mixture. The first reaction mixture is maintained for a time period sufficient to form a C1-C10 alkylenebis(chloro ester phosphonate) that is reacted under basic conditions with an excess of a hydroxylated compound to form a second reaction mixture that is itself maintained for a time period sufficient to form a C1-C10 alkylenebis(ester phosphonate) partial ester, homoleptic tetraester or mixed tetraester. The material so formed can be recovered or used as is.
• 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.
• Synthesis of Symmetrical Methylenebis(Alkyl Hydrogen Phosphonates) by Selective Cleavage of Methylenebis(Dialkyl Phosphonates) with Morpholine
  作者：Gantla Vidyasagar Reddy、Hollie K. Jacobs、Aravamudan S. Gopalan、Richard E. Barrans、Mark L. Dietz、Dominique C. Stepinski、Albert W. Herlinger

  DOI：10.1081/scc-120027271

  日期：2004.1

  c acids has been of recent interest due to their potential therapeutic applications. This paper describes a convenient method to prepare symmetrical methylenebis(alkyl hydrogen phosphonates) by the selective cleavage of the corresponding methylenebis(dialkyl phosphonate) with refluxing morpholine. The effects of structural variations on the amine as well as the substrate have been investigated to understand

  摘要 由于其潜在的治疗应用，亚甲基双膦酸偏酯的制备最近引起了人们的兴趣。本文描述了一种通过用回流的吗啉选择性裂解相应的亚甲基双（二烷基膦酸）来制备对称亚甲基双（烷基氢膦酸）的简便方法。已经研究了结构变化对胺和底物的影响，以了解该反应的范围和局限性。受阻双膦酸酯的一种更好的方法是使用吗啉裂解它们的二甲酯 4。该方法也可用于获取许多 C-烷基二烷基亚甲基双膦酸，例如 6。该研究清楚地表明，用吗啉裂解方便、便宜、