1,3-diphenyl-4-methyl-1H-2,1-benzoxaphosphinine 1-oxide | 1443465-33-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1,3-diphenyl-4-methyl-1H-2,1-benzoxaphosphinine 1-oxide
• 英文别名: 1,3-diphenyl-4-methyl-1H-2,1-benzoxaphosphorin-1-oxide；4-Methyl-1,3-diphenyl-2,1lambda5-benzoxaphosphinine 1-oxide；4-methyl-1,3-diphenyl-2,1λ5-benzoxaphosphinine 1-oxide
• CAS: 1443465-33-5
• 化学式: C₂₁H₁₇O₂P
• 分子量: 332.339
• InChiKey: PCAYVNUWLIVEEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-苯基-1-丁炔 、 二苯基磷酸 在 tris(acetonitrile)(η5-pentamethylcyclopentadienyl)rhodium(III) hexafluoroantimonate 、 silver(I) acetate 作用下， 以 二乙二醇二甲醚 为溶剂， 反应 2.0h， 以66%的产率得到1,3-diphenyl-4-methyl-1H-2,1-benzoxaphosphinine 1-oxide
  参考文献：
  名称：

  Rhodium(III)-catalyzed Oxidative Coupling through C–H Bond Cleavage Directed by Phosphinoxy Groups

  摘要：

  A straightforward synthesis of phosphaisocoumarins is achieved by the rhodium-catalyzed oxidative coupling of diarylphosphinic and phenylphosphonic acid derivatives with alkynes. The P-OH groups effectively act as the key function for the regioselective C-H bond cleavage. Related oxidative coupling of phenylphosphine oxides with alkenes can also be conducted smoothly under similar conditions.

  DOI：

  10.1021/ol4012794

文献信息

• Rhodium-Catalyzed Oxidative C-H Activation/Cyclization for the Synthesis of Phosphaisocoumarins and Phosphorous 2-Pyrones
  作者：Youngchul Park、Jungmin Seo、Sangjune Park、Eun Jeong Yoo、Phil Ho Lee

  DOI：10.1002/chem.201302652

  日期：2013.11.25

  Rhodium‐catalyzed cyclization of phosphinic acids and phosphonic monoesters with alkynes has been developed. The oxidative annulation proceeds with complete conversion of phosphinic acid derivatives and allowed the atom‐economic preparation of useful phosphaisocoumarins with high yield and selectivity. The reaction is tolerant of extensive substitution on the phosphinic acid, phosphonic monoester and alkyne, including

  已经开发了炔烃对次膦酸和膦酸单酯进行铑催化的环化反应。氧化环化反应可进行次膦酸衍生物的完全转化，从而可以经济高效地制备有用的磷化异香豆素，并实现了原子经济的制备。该反应耐受在次膦酸，膦酸单酯和炔烃上的广泛取代，包括卤化物，酮和羟基作为取代基。此外，我们发现烯基膦酸单酯通过与炔烃的氧化环化作用继续生成各种磷2-吡喃酮。机理研究表明，CH键金属化是限速步骤。
• NOVEL PHOSPHININE OXIDE DERIVATIVE AND PREPARATION METHOD THEREOF
  申请人：KNU-INDUSTRY COOPERATION FOUNDATION

  公开号：US20150344506A1

  公开（公告）日：2015-12-03

  Provided are a novel phosphinine oxide derivative and a preparation method thereof, and more specifically, the phosphinine oxide derivative includes an oxaphosphinine oxide derivative and an azaphosphinine oxide derivative. The phosphinine oxide derivative according to the present invention may have a pharmacological activity and a physiological activity, and may be used as a basic framework of a natural product and may be used for development of new drug and synthesis of various medical supplies. In addition, according to the preparation method of the phosphinine oxide derivative according to the present invention, various phosphinine oxide derivatives with a high yield may be prepared by a simple synthesis process using an intramolecular annulation between a phosphinic derivative and an alkyne derivative in the presence of a rhodium (Rh) catalyst or a ruthenium (Ru) catalyst and an oxidant.

  提供了一种新型的膦氧衍生物及其制备方法，更具体地说，该膦氧衍生物包括氧代膦环氧衍生物和氮代膦环氧衍生物。根据本发明的膦氧衍生物可能具有药理活性和生理活性，并可用作天然产物的基本框架，可用于新药的开发和各种医疗用品的合成。此外，根据本发明的膦氧衍生物的制备方法，可以通过在铑（Rh）催化剂或钌（Ru）催化剂和氧化剂存在下使用磷酸衍生物和炔烃衍生物之间的分子内环化的简单合成过程来制备各种收率高的膦氧衍生物。
• US9493494B2
  申请人：——

  公开号：US9493494B2

  公开（公告）日：2016-11-15