tetrahexyl methylenebisphosphonate | 3011-78-7

• 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: tetrahexyl methylenebisphosphonate
• 英文别名: methylenebis(dihexyl phosphonate)；tetra-n-hexyl methylenebisphosphonate；Tetrahexyl methylenediphosphonate；1-[dihexoxyphosphorylmethyl(hexoxy)phosphoryl]oxyhexane
• CAS: 3011-78-7
• 化学式: C₂₅H₅₄O₆P₂
• 分子量: 512.648
• InChiKey: NMMBDAYUXVALNI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  33
• 可旋转键数：
  26
• 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：

  tetrahexyl methylenebisphosphonate 在 sodium hydroxide 、 溴 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以91%的产率得到tetrahexyl (dibromomethylene)bisphosphonate
  参考文献：
  名称：

  Bisphosphonic compounds. Part 3. Preparation and identification of tetraalkyl methylene- and (α-halomethylene)bisphosphonates by mass spectrometry, NMR spectroscopy and X-ray crystallography

  摘要：

  The preparation and identification of tetraalkyl methylenebisphosphonates {XYC[P(O)(OR)2]2; X = Y = H, Cl or Br and R = alkyl} have been studied. Detailed procedures are given for the synthesis of XYC[P(O)(OR)2]2 (X = Y = H; R = hexyl; X = Y = Cl or Br and R = Me). H-1, C-13 and P-31 NMR data are reported including 1J(CH), 2J(CP), 3J(CP) and 2J(PP) coupling constants. The fragmentation of 19 XYC[P(O)(OR)2]2 has been studied in the gas phase. The solid state structures are given for two compounds (X = Y = Cl, R = Pr(i) and X = Y = Br, R = Me).

  DOI：

  10.1039/p29920000835
• 作为产物：
  描述：

  亚甲基双膦酰二氯 、 正己醇 在 四氮唑 、 N,N-二异丙基乙胺 作用下， 以 甲苯 为溶剂， 以85%的产率得到tetrahexyl methylenebisphosphonate
  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

• Partial esters of (Di) chloromethanediphosphonic acid useful for
  申请人：Leiras Oy

  公开号：US05376649A1

  公开（公告）日：1994-12-27

  Novel pharmaceutically active bisphosphonic acid derivatives of formula (I), in which R.sup.1, R.sup.2, R.sup.3 and R.sup.4 independently are C.sub.1 -C.sub.22 -alkyl, C.sub.2 -C.sub.22 -alkenyl, C.sub.2 -C.sub.22 -alkynyl, C.sub.3 -C.sub.10 -cycloalkyl, C.sub.3 -C.sub.10 -cycloalkenyl, aryl, aralkyl, silyl and hydrogen, and R.sup.4 is different from hydrogen, Q.sup.1 is hydrogen, fluorine, chlorine, bromine or iodine, and Q.sup.2 is chlorine, bromine or iodine, including the stereoisomers, such as the geometrical isomers and optically active isomers, of the compounds, as well as the pharmaceutically acceptable salts of the compounds. ##STR1##

  式（I）中新型药理活性双膦酸衍生物，其中 R.sup.1、R.sup.2、R.sup.3 和 R.sup.4 独立地为 C.sub.1 -C.sub.22 -烷基、C.sub.2 -C.sub.22 -烯基、C.sub.2 -C.sub.22 -炔基、C.sub.3 -C.sub.10 -环烷基、C.sub.3 -C.sub.10 -环烯基、芳基、芳基烷基、硅基和氢，且 R.sup.4 与氢不同，Q.sup.1 为氢、氟、氯、溴或碘，Q.sup.2 为氯、溴或碘，包括化合物的立体异构体，如几何异构体和光学活性异构体，以及化合物的药学上可接受的盐。
• Antimicrobial agents and process for their manufacture
  申请人：The Procter & Gamble Company

  公开号：US04820698A1

  公开（公告）日：1989-04-11

  Disclosed are tetraalkyl enthenylidenebisphosphonates and a method for their manufacture. These compounds are suitable for use as antimicrobial agents in combating a number of pathogenic microorganisms, such as bacteria, yeasts, viruses, fungi and protozoa, when used together with a pharmaceutically-acceptable carrier. Also disclosed is a method for treating infectious diseases by administering a safe and effective amount of these tetraalkyl ethenylidenebisphosphonates.

  揭示了四烷基乙烯基亚膦酸酯及其制备方法。这些化合物适用于作为抗微生物药剂，用于与一种药用可接受载体一起对抗多种致病微生物，如细菌、酵母菌、病毒、真菌和原生动物。还揭示了一种通过给予安全有效剂量的这些四烷基乙烯基亚膦酸酯来治疗传染病的方法。
• 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。
• Process for the manufacture of tetraalkyl ethenylidenebisphosphonate
  申请人：The Procter & Gamble Company

  公开号：US04939284A1

  公开（公告）日：1990-07-03

  Disclosed are tetraalkyl enthenylidenebisphosphonates and a method for their manufacture. These compounds are suitable for use as antimicrobial agents in combating a number of pathogenic microorganisms, such as bacteria, yeasts, viruses, fungi and protozoa, when used together with a pharmaceutically-acceptable carrier. Also disclosed is a method for treating infectious diseases by administering a safe and effective amount of these tetraalkyl ethenylidenebisphosphonates.

  本发明涉及四烷基乙烯基双膦酸酯及其制备方法。这些化合物适用于与药学上可接受的载体一起使用作为抗微生物剂，以对抗多种致病微生物，如细菌、酵母菌、病毒、真菌和原生动物。本发明还揭示了一种通过给予安全有效量的这些四烷基乙烯基双膦酸酯的方法来治疗感染性疾病。
• EP0479813A1
  申请人：——

  公开号：EP0479813A1

  公开（公告）日：1992-04-15