dimethyl 4-chlorobenzylphosphonate | 58358-45-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: dimethyl 4-chlorobenzylphosphonate
• 英文别名: (4-Chlorobenzyl)-phosphonic acid dimethyl ester；1-chloro-4-(dimethoxyphosphorylmethyl)benzene
• CAS: 58358-45-5
• 化学式: C₉H₁₂ClO₃P
• 分子量: 234.619
• InChiKey: FTUNFPLOAJZQKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  dimethyl 4-chlorobenzylphosphonate 在 五氯化磷 、 三乙胺 作用下， 以 四氯化碳 、 乙醚 为溶剂， 反应 4.0h， 生成 双(4-甲氧基苯基)4-氯苄基膦酸酯
  参考文献：
  名称：

  Nakamura, Mitsunobu; Sawasaki, Kouiti; Okamoto, Yoshiki, Journal of the Chemical Society. Perkin transactions I, 1994, # 1, p. 141 - 146

  摘要：

  DOI：
• 作为产物：
  描述：

  4-氯苯甲醇 在 bis(η3-allyl-μ-chloropalladium(II)) 、 三乙胺 、 双(2-二苯基磷苯基)醚 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 dimethyl 4-chlorobenzylphosphonate
  参考文献：
  名称：

  用磷亲核试剂对碳酸苄酯进行钯催化的苄基取代

  摘要：

  在钯催化剂 [Pd(η3-烯丙基)Cl]2-DPEphos 存在下，各种碳酸苄酯与膦酸二甲酯或氧化二苯基膦反应，以高产率得到苄基膦酸二甲酯和苄基二苯基氧化膦。催化膦酰化应用于从苄酯合成烯烃的一锅法。

  DOI：

  10.1246/cl.170901

文献信息

• Synthesis of α-Aryldiazophosphonates <i>via</i> a Diazo Transfer Reaction
  作者：Irina P. Beletskaya、Igor D. Titanyuk

  DOI：10.1021/acs.joc.1c02673

  日期：2022.3.4

  The simple synthetic procedure for preparation of α-aryl-α-diazophosphonates via a diazo transfer reaction is proposed. Benzylphosphonates reacted with tosyl azide (TsN3) in the presence of potassium tert-butoxide (KOtBu) to afford diazophosphonates in a yield up to 79%. The proposed method is general. The reaction uses easily available starting materials, tolerates various functional groups, and may

  提出了通过重氮转移反应制备α-芳基-α-重氮膦酸盐的简单合成方法。在叔丁醇钾 (KO t Bu)的存在下，膦酸苄酯与叠氮化甲苯磺酰 (TsN 3 ) 反应得到重氮膦酸酯，产率高达 79%。建议的方法是通用的。该反应使用容易获得的起始材料，耐受各种官能团，可用于数克规模的合成。
• A facile synthesis of α-phosphono esters through methoxycarbonylation of α-phosphono carbanions
  作者：Jon K.F. Geirsson、Jon T. Njardarson

  DOI：10.1016/0040-4039(94)88430-7

  日期：1994.11

  This paper describes a concise and effective synthesis of methyl α-phosphonoaryl acetates, effected by reacting α-phosphono carbanions with methyl chloroformate. Yields are high, and the purification of the products is readily achieved with column chromatography.

  本文描述了一种简明有效的甲基α-膦酰基芳基乙酸甲酯的合成方法，该方法通过使α-膦酰基碳负离子与氯甲酸甲酯反应来实现。产率高，并且通过柱色谱法容易地实现产物的纯化。
• Bridged bicyclic amine derivatives useful as CCR-3 receptor antagonists
  申请人：——

  公开号：US20040176416A1

  公开（公告）日：2004-09-09

  Compounds having the formula (I), Ar—(F)(E)-(CR 3 R 4 )—(CHR 5 ) m -(T)-(Q)-Ar 1 , are useful as CCR-3 receptor antagonists, wherein T is a bridged heterocyclyl group having one N atom and a bridge of one to two bridgehead carbon atoms; Ar and Ar 1 are aryl or heteroaryl; F is alkylene, alkenylene, or a bond; E is —C(═O)N(R 10 )—, —SO 2 N(R 10 )—, —N(R 11 )C(═O)N(R 10 O)—, —N(R 11 )SO 2 N(R 10 )—, —N(R 11 )C(═S)N(R 10 )—, —N(R 11 )C(═O)—, —N(R 11 )SO 2 —, —N(R 12 )C(═O)CH(R 13 )—, or CH(R 13 )C(═O)N(R 12 )—; Q is —C(═O)— or C 1-2 alkylene; and R 3 , R 4 , R 5 , R 9 , R 10 , R 11 , R 12 , and R 13 are defined as set forth in the specification.

  具有以下化学式的化合物(I)，Ar—(F)(E)-(CR3R4)—(CHR5)m-(T)-(Q)-Ar1，可用作CCR-3受体拮抗剂，其中T是具有一个N原子和一个到两个桥头碳原子的桥接杂环基团；Ar和Ar1是芳基或杂环芳基；F是烷基，烯烃基或键；E是—C(═O)N(R10)—，—SO2N(R10)—，—N(R11)C(═O)N(R10O)—，—N(R11)SO2N(R10)—，—N(R11)C(═S)N(R10)—，—N(R11)C(═O)—，—N(R11)SO2—，—N(R12)C(═O)CH(R13)—或CH(R13)C(═O)N(R12)—；Q是—C(═O)—或C1-2烷基；R3，R4，R5，R9，R10，R11，R12和R13如规范中所述定义。
• Palladium(II)-Catalyzed Ortho-Arylation of Benzylic Phosphonic Monoesters Using Potassium Aryltrifluoroborates
  作者：Xiangjian Meng、Sunggak Kim

  DOI：10.1021/jo401716p

  日期：2013.11.15

  The new monophosphonic acid directing group was successfully utilized in the Pd (II)-catalyzed orthoarylation of benzylic phosphonic monoesters using potassium aryltrifluoroborates. A wide range of benzylic phosphonic monoesters underwent clean ortho-arylation in high yields, and excellent functional group tolerance was also observed.
• Design and synthesis of novel CCR3 antagonists
  作者：Leyi Gong、J.Heather Hogg、James Collier、Robert S. Wilhelm、Carol Soderberg

  DOI：10.1016/s0960-894x(03)00748-0

  日期：2003.10

  As part of our investigation into the development of potent CCR3 antagonists, a series of piperidine analogues was designed and prepared. Exploration of the piperidine core examined both the basicity and the location of a nitrogen, as well as conformational variants. The bicyclo-piperidine 24c was found to be the most potent inhibitor of CCR3 with an IC50 of 0.0082 muM in the binding assay and 0.0024 muM in the chemotaxis assay. (C) 2003 Published by Elsevier Ltd.