diethyl (bromo(phenyl)methyl)phosphonate | 23755-78-4

• 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 (bromo(phenyl)methyl)phosphonate
• 英文别名: diethyl α-bromobenzylphosphinate；diethyl α-bromobenzylphosphonate；diethyl-α-bromobenzylphosphonate；α-bromobenzylphosphonic acid diethyl ester；Diethyl α-brombenzylphosphonat；alpha-Bromobenzylphosphonic acid diethyl ester；[bromo(diethoxyphosphoryl)methyl]benzene
• CAS: 23755-78-4
• 化学式: C₁₁H₁₆BrO₃P
• 分子量: 307.124
• InChiKey: DTDNZLDGEXIFGN-UHFFFAOYSA-N

物化性质

• 沸点：
  164-165 °C(Press: 1 Torr)
• 密度：
  1.3455 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  diethyl (bromo(phenyl)methyl)phosphonate 在 水 、 溴 作用下， 以 1,4-二氧六环 为溶剂， 生成 α-Brombenzylphosphonsaeure
  参考文献：
  名称：

  Chervenyuk,G.I.; Griner,G.V., Journal of general chemistry of the USSR, 1972, vol. 42, p. 2180 - 2183

  摘要：

  DOI：
• 作为产物：
  描述：

  苯基膦酸二乙酯 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 生成 diethyl (bromo(phenyl)methyl)phosphonate
  参考文献：
  名称：

  Grinev,G.V. et al., Journal of general chemistry of the USSR, 1969, vol. 39, p. 1223 - 1225

  摘要：

  DOI：

文献信息

• 4-Aminophenyldiphenylphosphinite (APDPP), a new heterogeneous and acid scavenger phosphinite — Conversion of alcohols, trimethylsilyl, and tetrahydropyranyl ethers to alkyl halides with halogens or <i>N</i>-halosuccinimides
  作者：Nasser Iranpoor、Habib Firouzabadi、Mohammad Gholinejad

  DOI：10.1139/v06-120

  日期：2006.7.1

  conversion of alcohols, trimethylsilyl ethers, and tetrahydropyranyl ethers to their corresponding bromides, iodides, and chlorides in the presence of molecular halogens or N-halosuccinimides. The amino group in this phosphinite acts as an acid scavenger and removes the produced acid. A simple filtration easily removes the phosphinate by-product.Key words: 4-aminophenyldiphenylphosphinite, alcohol, trimethylsilyl

  制备了一种新的非均相次膦酸盐，即 4-氨基苯基二苯基次膦酸盐 (APDPP)，并用于在分子卤素或 N-卤代琥珀酰亚胺存在下将醇、三甲基甲硅烷基醚和四氢吡喃基醚有效转化为其相应的溴化物、碘化物和氯化物。该次膦酸盐中的氨基充当酸清除剂并去除产生的酸。简单的过滤很容易去除副产物次膦酸盐。关键词：4-氨基苯基二苯基次膦酸盐，醇，三甲基甲硅烷基醚，四氢吡喃基醚，卤代烷。
• The iodine atom transfer addition reaction (I-ATRA) initiated by AIBN: Optimization, scope and radical reaction pathways
  作者：Piotr Bałczewski、Aldona Szadowiak、Tomasz Białas

  DOI：10.1002/hc.20187

  日期：——

  Optimization of reaction conditions (alkene, halide, solvent, stoichiometry, manners of the reagents addition, and reaction time) of the I-ATRA reactions involving 1-iodoalkylphosphonates was carried out. GC–MS–CI/EI analyses showed main and side products of this reaction and the corresponding radical reaction pathways leading to products derived from phosphorus and nonphosphorus containing iodides

  对涉及1-碘代烷基膦酸酯的I-ATRA反应的反应条件（烯烃、卤化物、溶剂、化学计量、试剂添加方式和反应时间）进行了优化。GC-MS-CI/EI 分析显示了该反应的主要和副产物以及相应的自由基反应途径，导致产物源自含磷和不含磷的碘化物，并解释了伴随 I-ATRA 的自由基还原过程中的氢来源反应。一些 3-碘代烷基和 3-碘代烯基膦酸酯的合成也基于优化的程序进行了介绍。© 2006 Wiley Periodicals, Inc. 杂原子化学 17:22–35, 2006; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20187
• PPh3/DDQ as a neutral system for the facile preparation of diethyl α-bromo, α-iodo and α-azidophosphonates from diethyl α-hydroxyphosphonates
  作者：Habib Firouzabadi、Nasser Iranpoor、Sara Sobhani

  DOI：10.1016/j.tet.2003.10.058

  日期：2004.1

  The mixture of triphenylphosphine (PPh3) and 2,3-dichloro-5,6-dicyanobenzquinone (DDQ) as a neutral system has been used for the preparation of various types of diethyl α-bromo, α-iodo and α-azidophosphonates from their corresponding diethyl α-hydroxyphosphonates in the presence of n-Bu4NBr, n-Bu4NI and NaN3 in good to high yields.

  三苯膦（PPh 3）和2,3-二氯-5,6-二氰基苯并醌（DDQ）的混合物已用作中性体系，用于从中制备各种类型的二乙基α-溴，α-碘和α-叠氮膦酸酯在n -Bu 4 NBr，n -Bu 4 NI和NaN 3的存在下，它们相应的α-羟基膦酸二乙酯的产率高到高。
• Controlled monohalogenation of phosphonates: A new route to pure α-monohalogenated diethyl benzylphosphonates
  作者：Bogdan Iorga、Frédéric Eymery、Philippe Savignac

  DOI：10.1016/s0040-4020(99)00037-x

  日期：1999.2

  Starting from diethyl benzylphosphonates, a wide variety of diethyl α-monofluoro, chloro, bromo and iodobenzylphosphonates have been obtained in pure form by a one-pot procedure. This high yielding method implies the intermediate protection of the benzyl anion with TMSCl followed by halogenation with an electrophilic halogenating reagent.

  从二乙基苄基膦酸酯开始，已经通过一锅法以纯净形式获得了多种α-单氟二乙基氯，氯代，溴代和碘代苄基膦酸酯。这种高产率的方法意味着用TMSC1对苄基阴离子进行中间保护，然后用亲电卤化试剂进行卤化。
• Preparation of styryl cyclopropane insecticide intermediates
  申请人：Bayer Aktiengesellschaft

  公开号：US04358409A1

  公开（公告）日：1982-11-09

  Styryl-cyclopropane derivatives of the formula ##STR1## in which R.sup.9 represents independently of one another when n=2, halogen, cyano, nitro, or an optionally halogen-substituted alkyl, alkoxy, alkylthio or alkylenedioxy radical, n represents zero, 1, 2, 3, 4 or 5, R.sup.10 represents hydrogen or halogen and Y represents acetyl, cyano or carbamoyl, are produced by reacting a benzylphosphonic acid ester of the formula ##STR2## in which R.sup.4 each independently represents alkyl or phenyl or together represent alkylene, with a formylcyclopropane derivative of the formula ##STR3## or by reacting an .alpha.-hydroxyphosphonic acid ester of the formula ##STR4## with an olefinating agent of the formula ##STR5## in which Z' represents a phosphorus-containing radical ##STR6## wherein R.sup.5 and R.sup.6 are identical or different and individually represent alkyl, phenyl, alkoxy or pehnoxy or R.sup.5 and R.sup.6 together represent alkanedioxy, R.sup.7 represents alkyl or phenyl and X represents halogen, in the presence of a base at a temperature between about -70.degree. and +150.degree. C. Other olefins can be similarly prepared. Many intermediates are new and the end products are themselves intermediates for insecticides.

  通过将具有以下结构的苯基磷酸酯与具有以下结构的酰基环丙烷衍生物反应，可以制备公式的苯基环丙烷衍生物： 其中R.sup.9表示独立的卤素，氰基，硝基或者一个可选择地取代卤素的烷基，烷氧基，烷基硫基或烷基二氧基基团时，当n=2时，n表示零，1，2，3，4或5，R.sup.10表示氢或卤素，Y表示乙酰基，氰基或者羰基。 或者通过将具有以下结构的α-羟基磷酸酯与具有以下结构的烯化试剂反应，也可以制备这些环丙烷衍生物： 其中Z'表示一个含磷基团，R.sup.5和R.sup.6相同或不同，分别表示烷基，苯基，烷氧基或苯氧基，或者R.sup.5和R.sup.6一起表示烷二氧基，R.sup.7表示烷基或苯基，X表示卤素，在碱存在下，在大约-70℃至+150℃的温度下进行反应。其他烯烃也可以类似地制备。许多中间体是新的，最终产物本身也是杀虫剂的中间体。