diethyl 1-chloroethylphosphonate | 10419-78-0

• 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: diethyl 1-chloroethylphosphonate
• 英文别名: Diethyl α-chloroethylphosphonate；O,O-diethylchloro-1 ethylphosphonate；(1-chloro-ethyl)-phosphonic acid diethyl ester；(1-Chlor-aethyl)-phosphonsaeure-diaethylester；<1-Chlor-ethyl>-phosphonsaeure-diethylester；1-Chlor-ethylphosphonsaeure-diethylester；1-(1-Chloroethyl-ethoxyphosphoryl)oxyethane；1-chloro-1-diethoxyphosphorylethane
• CAS: 10419-78-0
• 化学式: C₆H₁₄ClO₃P
• 分子量: 200.602
• InChiKey: HNKWDFZLWKGOGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2931900090

反应信息

• 作为反应物：
  描述：

  diethyl 1-chloroethylphosphonate 在 五氯化磷 、 三氯氧磷 作用下， 反应 4.0h， 以88%的产率得到(1-chloroethyl)phosphonyl dichloride
  参考文献：
  名称：

  Patois, C.; Berte-Verrando, S.; Savignac, P., Bulletin de la Societe Chimique de France, 1993, vol. 130, p. 485 - 487

  摘要：

  DOI：
• 作为产物：
  描述：

  三氯甲基膦酸二乙酯 在 正丁基锂 作用下， 生成 diethyl 1-chloroethylphosphonate
  参考文献：
  名称：

  Synthesis of Diethyl 1,1-Dichloroalkane- and 1-Chloroalkanephosphonates

  摘要：

  DOI：

  10.1055/s-1977-24498

文献信息

• Mild Synthesis of Organophosphorus Compounds:  Reaction of Phosphorus-Containing Carbenoids with Organoboranes
  作者：Monika I. Antczak、Jean-Luc Montchamp

  DOI：10.1021/ol800085u

  日期：2008.3.1

  Organoboranes react with phosphorus-containing carbenoids to produce a variety of functionalized organophosphorus compounds under mild conditions. In some cases, selective migration of one group attached to boron can be observed. Phosphonite-borane complexes are introduced as novel synthons for the synthesis of phosphinic esters.

  有机硼烷在温和条件下与含磷类卡宾反应生成多种功能化的有机磷化合物。在某些情况下，可以观察到与硼相连的一组选择性迁移。次膦酸酯-硼烷复合物被引入作为合成次膦酸酯的新型合成子。
• A new, effective approach for the CC bond formation utilizing 1-,2- and 3-phosphonyl substituted radicals derived from iodoalkylphosphonates and n-Bu3SnH/Et3B/O2 system
  作者：Piotr Balczewski、Witold M Pietrzykowski

  DOI：10.1016/s0040-4020(97)00405-5

  日期：1997.5

  A new, practical synthesis of highly substituted phosphonates utilizing 1-, 2- and 3-phosphonyl substituted radicals derived from iodoalkylphosphonates and a catalytic or stoichiometric amounts of the n-Bu3SnH/Et3B/O2 reagent system is described.

  描述了利用衍生自碘代烷基膦酸酯的1-，2-和3-膦酰基取代的基团和催化或化学计量的n- Bu 3 SnH / Et 3 B / O 2试剂体系的新型，实用的高取代膦酸酯的合成方法。
• Controlled Monohalogenation of Phosphonates, Part II: Preparation of Pure Diethyl α-Monohalogenated Alkylphosphonates
  作者：Bogdan Iorga、Frédéric Eymery、Philippe Savignac

  DOI：10.1055/s-2000-6375

  日期：——

  The reaction of diethyl alkylphosphonates with chlorotrimethylsilane in the presence of lithium diisopropylamide leads to the corresponding diethyl 1-lithio(trimethylsilyl)alkylphosphonates which are cleanly halogenated (X = F, Cl, Br, I) with electrophilic reagents and then deprotected to give pure diethyl a-monohalogenoalkylphosphonates. The reaction has been extended by the onepot conversion of

  在二异丙基氨基锂存在下，烷基膦酸二乙酯与三甲基氯硅烷反应生成相应的 1-锂硫（三甲基甲硅烷基）烷基膦酸二乙酯，该二乙酯用亲电子试剂完全卤化（X = F、Cl、Br、I），然后脱保护得到纯二乙基α-单卤代烷基膦酸酯。通过将磷酸三乙酯单锅转化为α-单卤代丁基膦酸二乙酯，该反应得到了扩展，总产率为 85-97%。
• New syntheses of 1-chloroalkylphosphinates
  作者：Xavier Morise、Philippe Savignac、Jean-Marc Denis

  DOI：10.1039/p19960002179

  日期：——

  Different approaches to the synthesis of 1-chloroalkylphosphinates are described. Initially, we tried to extend a reaction described by Kabachnik for the preparation of chloromethylphosphinic acid chlorides [R1(Cl)P(O)CH2Cl] to C-substituted derivatives. We also considered the possibility of synthesizing the title compounds by routes already described for the formation of diethyl 1-chloroalkylphosphonates. Although these methods have allowed us to obtain several of the desired phosphinates, they suffer from limitations that restrict their synthetic applications. Finally, we have developed a more general approach that allows the formation of a wide range of phosphinates. It involves a selective P–C bond formation by reaction of MeMgCl and PhMgCl with phosphonochloridates, which are prepared by P-chlorination of 1-chloroalkylphosphonates.

  描述了合成1-氯烷基膦酸酯的不同方法。最初，我们尝试扩展Kabachnik所描述的用于制备氯甲基膦酸氯化物[R1(Cl)P(O)CH2Cl]的反应，以适应C取代衍生物。我们还考虑了通过已描述的合成二乙基1-氯烷基膦酸酯的途径来合成目标化合物。尽管这些方法已使我们获得了几个所需的膦酸酯，但它们存在限制，从而限制了它们的合成应用。最后，我们开发了一种更通用的方法，允许形成广泛的膦酸酯。这涉及通过MeMgCl和PhMgCl与由1-氯烷基膦酸酯的P-氯化反应制备的膦酸氯化物的反应形成选择性的P–C键。
• Asymmetric Synthesis of α-Methylphosphophenylalanine Derivatives Using Sulfinimine-Derived Enantiopure Aziridine-2-phosphonates
  作者：Franklin A. Davis、William McCoull、Donald D. Titus

  DOI：10.1021/ol990855k

  日期：1999.10.1

  [formula: see text] 2-Methylaziridine-2-phosphonates were prepared from enantiopure sulfinimines and were demonstrated to be versatile synthetic intermediates for the synthesis of novel alpha-disubstituted and alpha,beta-trisubstituted alpha-aminophosphonate derivatives. The first asymmetric synthesis of both enantiomers of alpha-methylphosphophenylalanine is described.

  由对映体纯的亚磺酸亚胺制备2-甲基氮丙啶-2-膦酸酯，并证明是合成新型α-二取代和α，β-三取代的α-氨基膦酸酯衍生物的通用合成中间体。描述了α-甲基磷酸苯丙氨酸的两种对映体的第一次不对称合成。