(3,3-diphenylpropa-1,2-dien-1-yl)diphenylphosphine oxide | 15729-20-1

• 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: (3,3-diphenylpropa-1,2-dien-1-yl)diphenylphosphine oxide
• 英文别名: (3-Diphenylphosphoryl-1-phenylpropa-1,2-dienyl)benzene
• CAS: 15729-20-1
• 化学式: C₂₇H₂₁OP
• 分子量: 392.437
• InChiKey: XAWSFKOBZWHXLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  (3,3-diphenylpropa-1,2-dien-1-yl)diphenylphosphine oxide 在 叔丁基过氧化氢 、 copper(ll) bromide 作用下， 以 四氢呋喃 、 癸烷 为溶剂， 反应 24.0h， 以85%的产率得到[(E)-2-bromo-3-hydroxy-3,3-diphenylprop-1-en-1-yl]diphenylphosphine oxide
  参考文献：
  名称：

  CuBr2 / TBHP促进（Diphenylphosphoryl）Allenes的选择性二溴化和溴羟基化

  摘要：

  协作的CuBr 2和叔丁基过氧化氢（TBHP）系统允许在温和条件下进行（diphenylphosphoryl）alenes的高度立体选择性二溴化和溴羟化反应。

  DOI：

  10.1002/ejoc.201700187
• 作为产物：
  描述：

  1,1-二苯基-2-丙炔-1-醇 在 4-二甲氨基吡啶 、 copper(l) iodide 、 四甲基乙二胺 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (3,3-diphenylpropa-1,2-dien-1-yl)diphenylphosphine oxide
  参考文献：
  名称：

  铜催化P（O）H化合物与乙酸炔丙酯的铜偶联反应，可轻松合成烯基磷酰基化合物

  摘要：

  开发了一种新的Cu催化的炔丙基乙酸酯与P（O）H化合物的铜催化取代反应，可通过CP键偶联在温和的条件下以高收率得到烯丙基磷酰基化合物。一个合理的机制...

  DOI：

  10.1039/c6cc02563c

文献信息

• I ₂ /TBHP Mediated Divergent C(sp ² )‐P Cleavage of Allenylphosphine Oxides: Substituent‐Controlled Regioselectivity
  作者：Teng Liu、Jie Zhu、Xue Sun、Liang Cheng、Lei Wu

  DOI：10.1002/adsc.201900334

  日期：2019.8.5

  regioselective C(sp2)‐P(O) cleavage of allenylphosphine oxides mediated by I2/TBHP is achieved for the first time. The divergent pathway via cleavage of (Ph)C−P(O) or (allene)C−P(O) modulated by substituents, renders the formation of 4‐iodo‐2‐phenyl‐5H‐1,2‐oxa‐phosphole 2‐oxide and α‐iodoenone derivatives, respectively. A plausible mechanism through radical pathways, along with the cleavage of phenyl and diphenylphosphine

  首次实现了由I 2 / TBHP介导的烯丙基膦氧化物的高区域选择性C（sp 2）-P（O）裂解。通过取代基调节的（Ph）C-P（O）或（丙二烯）C-P（O）裂解的发散途径导致形成4-碘-2--2-苯基-5 H -1,2-氧杂-分别是2-氧化物和α-碘烯酮衍生物。捕获实验和18个O同位素标记研究证实了通过自由基途径以及裂解苯基和二苯基膦氧化物部分的合理机制。
• Cumulated Trienephosphine Oxides. Bimolecular Trapping of an Alkylidenecyclopropylidene
  作者：Christiane Santelli-Rouvier、Loïc Toupet、Maurice Santelli

  DOI：10.1021/jo970771u

  日期：1997.12.1

  Dihalocarbene addition to allenic phosphine oxides occurs mainly at the allylic double bond. Treatment of dibromocarbene adducts with BuLi leads to cumulated trienephosphine oxides. In some cases, the intermediate alkylidenecyclopropylidene (or its precursor) is exceptionally stabilized, and this carbene (or carbenoid) is trapped by the corresponding cumulated trienephosphine oxide in a bimolecular process. The resultant spiropentane is formed in a regio- and stereoselective manner.
• A new method for the synthesis of [3]-cumulenes and eneynecumulenes related to neocarzinostatin chromophore
  作者：Isao Saito、Kazuhiro Yamaguchi、Ryu Nagata、Eiji Murahashi

  DOI：10.1016/s0040-4039(00)88518-4

  日期：1990.1

  A convenient method for the synthesis of [3]-cumulenes based on a Horner-Emmons type reaction of allenyldiphenylphosphine oxides with aldehydes or ketones has been described. A facile two-step synthesis of eneynecumulenes has been accomplished by this method.
• Studies on highly regio- and stereoselective fluorohydroxylation reaction of 3-aryl-1,2-allenyl phosphine oxides with Selectfluor
  作者：Guangke He、Chunling Fu、Shengming Ma

  DOI：10.1016/j.tet.2009.07.009

  日期：2009.9

  The fluorohydroxylation of allenyl phosphine oxides with Selectfluor in commercial MeCN without prior treatment or a mixed solvent of anhydrous MeCN (refluxed over CaH2 and distilled before use) and 7.0 equiv of H2O or MeNO2/H2O=10/1 afforded 2-fluoro-3-hydroxy-1(E)-alkenyl diphenyl phosphine oxides in moderate yields with very high regio- and stereoselectivities. The E-stereoselectivity is believed to be controlled by the phosphine oxide functionality. In the reaction of 3-(4-methoxyphenyl)-1,2-propadienyl diphenyl phosphine oxide, further fluorination on the electron-rich phenyl ring was also observed. (C) 2009 Elsevier Ltd. All rights reserved.
• Cumulated trienephosphine oxides. Trapping of an alkylidenecyclopropylidene
  作者：Christiane Santelli-Rouvier、Maurice Santelli

  DOI：10.1016/s0040-4039(00)74758-7

  日期：1992.12

  Treatment by BuLi of dibromocarbene adducts on allenic phosphine oxides leads to alkylidenecyclopropylidene that, in one case, is an exceptional stabilized cyclopropylidene: this carbene is trapped by the corresponding cumulated trienephosphine oxide in a bimolecular process.