phenyl(1-phenylethyl)phosphinic chloride | 140458-23-7

• 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: phenyl(1-phenylethyl)phosphinic chloride
• 英文别名: Phosphinic chloride, phenyl(1-phenylethyl)-；1-[chloro(phenyl)phosphoryl]ethylbenzene
• CAS: 140458-23-7
• 化学式: C₁₄H₁₄ClOP
• 分子量: 264.691
• InChiKey: CMPOCRKFXWWFOG-UHFFFAOYSA-N

物化性质

• 沸点：
  422.2±28.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  phenyl(1-phenylethyl)phosphinic chloride 以57%的产率得到
  参考文献：
  名称：

  Harger Martin J. P., Sreedharan-Menon Ramesh, J. Chem. Soc. Perkin Trans. 1, (1994) N 22, S 3261-3267

  摘要：

  DOI：
• 作为产物：
  描述：

  ethyl benzyl(phenyl)phosphinate 在 盐酸 、 正丁基锂 、 草酰氯 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 14.5h， 生成 phenyl(1-phenylethyl)phosphinic chloride
  参考文献：
  名称：

  立体定向性在的重排反应Ñ -phosphinoyl- ö -sulfonylhydroxylamine用甲胺和叔丁基胺：在磷作为初步形成一个phosphonamidic磺酸混合酸酐的证据配置的保持

  摘要：

  所述的反应Ñ -phosphinoyl- Ô（PH）（O）-sulfonylhydroxylamine PhMeCH P NHOMs 10与RNH 2（R = Me或卜吨）导致从磷的苯基的迁移到氮这导致重排产物PhMeCHP（ O）（NHPh）NHR。使用富含一种非对映异构体（80:20）或另一种（3:97）的10种样品，与纯净RNH 2的反应具有高度立体特异性，从而排除了游离的偏亚膦酸酯中间体的可能性。对于MeNH 2反应中，从底物和产物的X射线晶体结构推断出其相对构型，显示出立体特异性的感觉，即保留了磷的构型。为卜牛逼NH 2反应，间接证据导致了同样的结论。构型的保留被认为是由于最初的碱基诱导的重排导致了膦酰胺磺酸混合酸酐PhMeCHP（O）（NHPh）OMs的转变，而磷的构型却发生了反转。然后用RNH 2进行亲核取代，得到所观察到的产物。亲核取代可具有缔合的S N2（P）机理（磷的构

  DOI：

  10.1039/p19940003261

文献信息

• Lossen-like rearrangement of N-[α-methylbenzyl(phenyl)phosphinoyl]-O-methylsulfonylhydroxylamine with methylamine: retention of configuration at phosphorus as revealed by X-ray crystallography
  作者：John Fawcett、Martin J. P. Harger、Ramesh Sreedharan Menon

  DOI：10.1039/c39920000227

  日期：——

  The diastereoisomers of the title compound 6 rearrange with high stereospecificity on treatment with MeNH2, giving PhMeCHP(O)(NHMe)NHPh in which the migrating phenyl group has been replaced by MeNH2 with retention of configuration at phosphorus.

  标题化合物6的非对映异构体在与MeNH2反应时以高立体特异性重排，生成PhMeCHP(O)(NHMe)NHPh，其中迁移的苯基被MeNH2替换，同时保持了磷的构型。
• Diastereoselective and Intramolecular Cycloadditions of Asymmetric <i>P-</i>Nitroso Phosphine Oxides
  作者：Roy W. Ware、Cynthia S. Day、S. Bruce King

  DOI：10.1021/jo0202839

  日期：2002.8.1

  Benzyl phenyl P-nitroso phosphine oxide (5) reacts as an N-O heterodienophile with 1,3-cyclopentadiene to give the diastereomeric cycloadducts 6a,b in a ratio of 1.5:1 (6a:6b). The same reaction in the presence of tin tetrachloride produces 6a,b in a ratio of 2.9:1 (6a:6b). Cycloaddition of the structurally modified P-nitroso phosphine oxide (18) with 1,3-cyclopentadiene forms the diastereomeric cycloadducts 16a,b in a ratio of 3.1:1 (16a:16b). These results suggest the reactions of these P-nitroso phosphine oxides and 1,3-cyclopentadiene occur through a transition state where the heterodienophile adopts an s-cis conformation and approaches the diene in an exo fashion syn to the phenyl group. This model resembles those proposed for the cycloadditions of the structurally similar asymmetric vinyl phosphine oxides. Reaction of 18 with 1,3-cyclopentadiene in the presence of a Lewis acid produces cycloadducts 16ab in a ratio of 7:1 (16a:16b), which approaches synthetic utility. Similar experiments show that 1,3-cyclohexadiene likely reacts with P-nitroso phosphine oxides through a different transition state, limiting current predictions regarding the diastereoselectivity of these reactions. The intramolecular cycloaddition of an asymmetric P-nitroso phosphine oxide (19) for the first time produces a unique phosphorus-containing heterocyclic compound (20).
• Harger, Martin J. P.; Sreedharan-Menon, Ramesh, Journal of the Chemical Society. Perkin Transactions 2 (2001), 1999, # 2, p. 159 - 163
  作者：Harger, Martin J. P.、Sreedharan-Menon, Ramesh

  DOI：——

  日期：——