1-Phenyl-2,3-dihydrophosphindole | 86901-22-6

• 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: 1-Phenyl-2,3-dihydrophosphindole
• 英文别名: 1-phenyl-2,3-dihydrobenzo[b]phosphole
• CAS: 86901-22-6
• 化学式: C₁₄H₁₃P
• 分子量: 212.231
• InChiKey: YHCQAOQKUDPICR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-Phenyl-2,3-dihydrophosphindole 、 Phenyl-cis-2-styrylphosphine 在 双氧水 作用下， 以 苯 为溶剂， 反应 18.0h， 以0.2 g的产率得到1-phenyl-2,3-dihydrobenzo[b]phosphole-1-oxide
  参考文献：
  名称：

  1-Phenyl-cis-3a,7a-dihydrophosphindole and its properties

  摘要：

  DOI：

  10.1021/jo00169a029
• 作为产物：
  描述：

  邻溴苯乙酸 在 sodium tetrahydroborate 、 草酰氯 、 三氟化硼乙醚 、 叔丁基锂 、 三溴化磷 作用下， 以 四氢呋喃 、 二氯甲烷 、 正戊烷 为溶剂， 反应 41.75h， 生成 1-Phenyl-2,3-dihydrophosphindole
  参考文献：
  名称：

  Synthesis of 2,3-Dihydro-1-phenylbenzo[b]phosphole (1-Phenylphosphindane) and Its Use as a Mechanistic Test in the Asymmetric Appel Reaction: Decisive Evidence against Involvement of Pseudorotation in the Stereoselecting Step

  摘要：

  Racemic 2,3-dihydro-1-phenylbenzo[b]-phosphole was obtained by reduction of 1-phenylbenzo[b]-phosphole-1-oxide, itself derived by ring-dosing metathesis of phenylstyrylvinylphosphine oxide. The title compound was then reoxidized under asymmetric Appel conditions. Comparison of the sense and degree of the stereoselectivity to those obtained with an open-chain analogue indicated that the ring system does not affect the selectivity of the process. This in turn strongly suggests that the stereoselection is not related to pseudorotamer preferences in putative phosphorane intermediates.

  DOI：

  10.1021/jo401318g

文献信息

• Enantioselective Synthesis of P-Stereogenic Benzophospholanes via Palladium-Catalyzed Intramolecular Cyclization
  作者：Tim J. Brunker、Brian J. Anderson、Natalia F. Blank、David S. Glueck、Arnold L. Rheingold

  DOI：10.1021/ol0700512

  日期：2007.3.1

  Enantioselective or diastereoselective intramolecular cyclization of functionalized secondary phosphines or their borane adducts catalyzed by chiral Pd(diphosphine) complexes gave P-stereogenic benzophospholanes in up to 70% ee. These results provide a new method for the synthesis of chiral phospholanes, which are valuable ligands in asymmetric catalysis. [reaction: see text]

  对映体选择性或非对映体选择性分子内环化的功能化的二级膦或其手性Pd（二膦）配合物催化的硼烷加合物，在高达70％ee的条件下生成了P-立体异构苯并膦酸酯。这些结果提供了一种合成手性膦酸酯的新方法，手性膦酸酯是不对称催化中有价值的配体。[反应：看文字]
• QUIN, L. D.;RAO, N. S., J. ORG. CHEM., 1983, 48, N 21, 3754-3759
  作者：QUIN, L. D.、RAO, N. S.

  DOI：——

  日期：——
• Synthesis of 2,3-Dihydro-1-phenylbenzo[<i>b</i>]phosphole (1-Phenylphosphindane) and Its Use as a Mechanistic Test in the Asymmetric Appel Reaction: Decisive Evidence against Involvement of Pseudorotation in the Stereoselecting Step
  作者：Damien J. Carr、Jaya Satyanarayana Kudavalli、Katherine S. Dunne、Helge Müller-Bunz、Declan G. Gilheany

  DOI：10.1021/jo401318g

  日期：2013.10.18

  Racemic 2,3-dihydro-1-phenylbenzo[b]-phosphole was obtained by reduction of 1-phenylbenzo[b]-phosphole-1-oxide, itself derived by ring-dosing metathesis of phenylstyrylvinylphosphine oxide. The title compound was then reoxidized under asymmetric Appel conditions. Comparison of the sense and degree of the stereoselectivity to those obtained with an open-chain analogue indicated that the ring system does not affect the selectivity of the process. This in turn strongly suggests that the stereoselection is not related to pseudorotamer preferences in putative phosphorane intermediates.
• 1-Phenyl-cis-3a,7a-dihydrophosphindole and its properties
  作者：Louis D. Quin、Nandakumar S. Rao

  DOI：10.1021/jo00169a029

  日期：1983.10