ethanediyl-bis-phosphinic acid tetrachloride | 1499-30-5

• 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: ethanediyl-bis-phosphinic acid tetrachloride
• 英文别名: 1,2-Ethandiylbis(phosphonsaeuredichlorid)；ethylenebis(phosphonic dichloride)；Ethandiphosphonsaeure-(1,2)-tetrachlorid；Ethylen-diphosphonsaeure-tetrachlorid；Ethylen-bis-phosphonsaeure-dichlorid；1,2-Ethan-bis-phosphonylchlorid；Ethane-1,2-diyldiphosphonic Dichloride；1,2-bis(dichlorophosphoryl)ethane
• CAS: 1499-30-5
• 化学式: C₂H₄Cl₄O₂P₂
• 分子量: 263.812
• InChiKey: HSSWJZQNPFSPPQ-UHFFFAOYSA-N

物化性质

• 熔点：
  155-157 °C (decomp)
• 沸点：
  350.4±25.0 °C(Predicted)
• 密度：
  1.697±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethanediyl-bis-phosphinic acid tetrachloride 在 三氟化砷 作用下， 反应 3.0h， 以67.5%的产率得到1,2-Ethandiylbis(phosphonsaeuredifluorid)
  参考文献：
  名称：

  Althoff, Wolfgang; Fild, Manfred; Schmutzler, Reinhard, Chemische Berichte, 1981, vol. 114, # 3, p. 1082 - 1090

  摘要：

  DOI：
• 作为产物：
  描述：

  tetraisopropyl ethylenediphosphonate 在 五氯化磷 作用下， 生成 ethanediyl-bis-phosphinic acid tetrachloride
  参考文献：
  名称：

  关于伯胺使含P–N–P骨架的化合物环化的新发现；二膦酰基甲烷的延伸

  摘要：

  二氯膦（二氯膦酰基）甲胺Cl 2 P·NMe·P（O）Cl 2与3摩尔当量的叔丁基胺反应，得到环二膦氮烷Cl [ t ] 。与此相反，（BU吨HN）[图形省略]卜吨是从有Cl的类似反应中分离的唯一产品2 P·NME·P（S）氯2。Cl 2（O）P·CH 2 ·P（O）Cl 2与NH 2 Bu t和NH 2 Pr i的相似反应给出了新的一类环化合物，Cl（O）我或卜吨）（1,2,4-氮杂二磷杂环戊烷），但从与Cl 2（O）P·CH 2 ·CH 2 ·P（O）Cl 2的类似反应中未发现环状产物。的（ME试图环化2 N）氯（O）P-CH 2 -P（O）Cl（上NME 2）由NH 2卜吨给出了一个无环产物。（BU吨HN）（ME 2 N）（O）P·CH 2 ·P（O）（NME 2）（NHBu吨），而不是（ME 2 N）（O）[图形省略]卜吨。后者的环状衍生物，是通过加热（Me 2 N）2（O）P·CH获得的2

  DOI：

  10.1039/dt9760001113

文献信息

• Organische Phosphorverbindungen XVII. Darstellung von Alkylen-bis-phosphonsäurechloriden und Alkylen-bis-thiophosphonsäurechloriden und deren Reaktion mit G<scp>RIGNARD</scp>-Verbindungen
  作者：Ludwig Maier

  DOI：10.1002/hlca.19650480114

  日期：——

  The synthesis and some physical properties of alkylene bis-(phosphonic dichlorides), Cl2P(O)(CH2)n(O)PCl2, and of alkylene bis-(phosphonothioic dichlorides), Cl2P(S)(CH2)n(S)PCl2, a new class of compounds, are reported. The reactions of alkylene bis-(phosphonothioic dichlorides) with GRIGNARD reagents and of CH3P(S)Br2 with di-GRIGNARD reagents are also described. Some physical properties of several

  亚烷基双-（膦酰二氯），Cl 2 P（O）（CH 2）n（O）PCl 2和亚烷基双-（硫代磷酸二氯），Cl 2 P（S）（CH）的合成及一些物理性质2）n（S）PCl 2是一种新型化合物。还描述了亚烷基双-（硫代硫代二氯化膦）与GRIGNARD试剂的反应以及CH 3 P（S）Br 2与di-GRIGNARD试剂的反应。已经确定了几种二膦二硫化物和两种环状叔膦硫化物的一些物理性质。
• [EN] NUCLEOSIDE 5'-PHOSPHOROTHIOATE ANALOGUES AND USES THEREOF<br/>[FR] ANALOGUES DE NUCLÉOSIDE 5'-PHOSPHOROTHIOATE ET LEURS UTILISATIONS
  申请人：UNIV BAR ILAN

  公开号：WO2013132489A1

  公开（公告）日：2013-09-12

  The invention provides particular mono- and dinucleoside 5'-phosphorothioate analogues, more particularly mono- or di- adenosine or uridine 5'-di- or tri- phosphorothioate analogues in which at least one of the bridging oxygen atoms of the phosphorothioate is replaced by a group such as -CH2-, and at least one of the non- bridging atoms or negatively-charged atoms of the phosphorothioate is either a sulfur atom or a sulfur ion; and pharmaceutical compositions thereof. These compounds are useful for treatment of neurodegenerative diseases or disorders such as Alzheimer's disease.

  该发明提供了特定的单核苷酸和二核苷酸5'-磷硫酸酯类似物，更具体地说是单腺苷或尿苷5'-二磷硫酸酯类似物或三磷硫酸酯类似物，其中磷硫酸酯的桥氧原子之一被类似于-CH2-的基团取代，并且磷硫酸酯的非桥接原子或负电荷原子之一是硫原子或硫离子；以及其药物组合物。这些化合物可用于治疗神经退行性疾病或障碍，如阿尔茨海默病。
• A novel access to alicyclic phosphine oxides via ring closing metathesis
  作者：M. Trevitt、V. Gouverneur

  DOI：10.1016/s0040-4039(99)01534-8

  日期：1999.10

  A series of cyclic phosphine oxides 5a-e was prepared in a one-step procedure by RCM of dienes 4a-e. The methodology was extended to the preparation of the bis-phosphine oxide 5f. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.
• Reaction of dibromoalkanes with silyl phosphites. Synthesis and properties of mono-and diphosphonoalkanes
  作者：M. A. Pudovik、S. A. Terent’eva、L. K. Kibardina、A. N. Pudovik

  DOI：10.1134/s1070363206050094

  日期：2006.5

  Reactions of dibromoethane and dibromopropane with silyl phosphites are studied. Mono- and diphosphonoalkanes of various structures were prepared, and their chemical properties were studied.
• Cofactor-type inhibitors of inosine monophosphate dehydrogenase via modular approach: Targeting the pyrophosphate binding sub-domain
  作者：Krzysztof Felczak、Liqiang Chen、Daniel Wilson、Jessica Williams、Robert Vince、Riccardo Petrelli、Hiremagalur N. Jayaram、Praveen Kusumanchi、Mohineesh Kumar、Krzysztof W. Pankiewicz

  DOI：10.1016/j.bmc.2011.01.042

  日期：2011.3

  Cofactor-type inhibitors of inosine monophosphate dehydrogenase (IMPDH) that target the nicotinamide adenine dinucleotide (NAD) binding domain of the enzyme are modular in nature. They interact with the three sub-sites of the cofactor binding domain; the nicotinamide monophosphate (NMN) binding sub-site (N sub-site), the adenosine monophosphate (AMP) binding sub-site (A sub-site), and the pyrophosphate binding sub-site (P sub-site or P-groove). Mycophenolic acid (MPA) shows high affinity to the N sub-site of human IMPDH mimicking NMN binding. We found that the attachment of adenosine to the MPA through variety of linkers afforded numerous mycophenolic adenine dinucleotide (MAD) analogues that inhibit the two isoforms of the human enzyme in low nanomolar to low micromolar range. An analogue 4, in which 2-ethyladenosine is attached to the mycophenolic alcohol moiety through the difluoromethylenebis(phosphonate) linker, was found to be a potent inhibitor of hIMPDH1 (K-i = 5 nM), and one of the most potent, sub-micromolar inhibitor of leukemia K562 cells proliferation (IC50 = 0.45 mu M). Compound 4 was as potent as Gleevec (IC50 = 0.56 mu M) heralded as a 'magic bullet' against chronic myelogenous leukemia (CML). MAD analogues 7 and 8 containing an extended ethylenebis(phosphonate) linkage showed low nanomolar inhibition of IMPDH and low micromolar inhibition of K562 cells proliferation. Some novel MAD analogues described herein containing linkers of different length and geometry were found to inhibit IMPDH with K-i's lower than 100 nM. Thus, such linkers can be used for connection of other molecular fragments with high affinity to the N- and A-sub-site of IMPDH. (C) 2011 Elsevier Ltd. All rights reserved.