diphenyl(3-phenylbuta-1,2-dien-1-yl)phosphine oxide | 1190882-59-7

• 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: diphenyl(3-phenylbuta-1,2-dien-1-yl)phosphine oxide
• 英文别名: 3-phenyl-1-(diphenylphosphoryl)buta-1,2-diene；3-phenylbuta-1,2-dienyl diphenyl phosphine oxide
• CAS: 1190882-59-7
• 化学式: C₂₂H₁₉OP
• 分子量: 330.366
• InChiKey: PNQYUDQFOQYLDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 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：

  diphenyl(3-phenylbuta-1,2-dien-1-yl)phosphine oxide 在 水 、 Selectfluor 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以66%的产率得到2-fluoro-3-hydroxy-3-phenyl-1(E)-butenyl diphenyl phosphine oxide
  参考文献：
  名称：

  Studies on highly regio- and stereoselective fluorohydroxylation reaction of 3-aryl-1,2-allenyl phosphine oxides with Selectfluor

  摘要：

  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.

  DOI：

  10.1016/j.tet.2009.07.009
• 作为产物：
  描述：

  2-苯基-3-丁炔-2-醇 、 二苯基氯化膦 在 吡啶 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 diphenyl(3-phenylbuta-1,2-dien-1-yl)phosphine oxide
  参考文献：
  名称：

  I2 / TBHP介导的烯丙基膦氧化物的C（sp2）-P发散裂解：取代基控制的区域选择性

  摘要：

  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。

  DOI：

  10.1002/adsc.201900334

文献信息

• Visible‐Light‐Promoted Regio‐ and Stereoselective Oxyalkenyl‐ation of Phosphinyl Allenes
  作者：Xue Sun、Teng Liu、Yan‐Tong Yang、Yue‐Jie Gu、Yu‐Wei Liu、Yi‐Gang Ji、Kai Luo、Jie Zhu、Lei Wu

  DOI：10.1002/adsc.202000214

  日期：2020.7.16

  time. This protocol, merging visible light photoredox and palladium catalysis, provides a direct approach to conjugated tertiary allylic alcohol derivatives with broad functional group tolerance in moderate to excellent yields. Mechanistic studies suggest that, although two possible pathways exist in the transformation, radical oxyalkenylation promoted by visible light photoredox takes over the major

  首次揭示了次膦基烯丙基的高度区域和立体选择性的氧烯基化。该协议，结合了可见光的光氧化还原和钯催化作用，提供了一种直接的方法，以中等到极好的收率，具有宽泛的官能团耐受性的共轭叔烯丙基醇衍生物。机理研究表明，尽管转化中存在两个可能的途径，但可见光光氧化还原促进的自由基氧烯基化作用占据了主要途径。
• Convenient synthesis of allenylphosphoryl compounds via Cu-catalysed couplings of P(O)H compounds with propargyl acetates
  作者：Ruwei Shen、Bing Luo、Jianlin Yang、Lixiong Zhang、Li-Biao Han

  DOI：10.1039/c6cc02563c

  日期：——

  A novel Cu-catalysed substitution reaction of propargyl acetates with P(O)H compounds is developed to afford allenylphosphoryl compounds via C-P bond coupling in high yields under mild conditions. A plausible mechanism...

  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...
• CuBr₂ /TBHP-Promoted Selective Dibromination and Bromohydroxylation of (Diphenylphosphoryl)allenes
  作者：Tian Liu、Jing Sun、Qiang Wang、Lei Li、Ming-Dong Zhou

  DOI：10.1002/ejoc.201700187

  日期：2017.4.10

  A cooperative CuBr2 and tert‐butyl hydroperoxide (TBHP) system allowed for the highly stereoselective dibromination and bromohydroxylation reactions of (diphenylphosphoryl)allenes under mild conditions.

  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。
• Acid-promoted transformations of aryl substituted diphenylphosphoryl allenes
  作者：Stanislav V. Lozovskiy、Alexander S. Bogachenkov、Albina V. Dogadina、Aleksander V. Vasilyev

  DOI：10.1016/j.tetlet.2016.06.026

  日期：2016.7

  1-(Diphenylphosphoryl)alka-1,2-dienes, bearing aryl substituents at the allene system, under the action of Brønsted (TfOH, H2SO4) or Lewis (AlCl3) acids gave rise to 3-hydroxyalk-2-en-1-yl-diphenylphosphine oxides (diphenylphosphoryl allyl alcohols) in yields of 57–98%. In some cases, the formation of (diphenylphosphoryl)indenes and phosphaheterobicyclic structures was observed.

  在布朗斯台德（TfOH，H 2 SO 4）或路易斯（AlCl 3）酸的作用下，在丙二烯体系上带有芳基取代基的1-（二苯基磷酰基）烷基-1,2-二烯生成3-羟基烷-2-烯-1-基二苯基膦氧化物（二苯基磷酰基烯丙醇），产率为57–98％。在某些情况下，观察到了（二苯基磷酰基）茚和磷杂双环结构的形成。
• Zn(OTf)2 catalyzed addition–cyclization reaction of allenylphosphine oxides with propargyl alcohol-unexpected formation of 2,5-dimethylenetetrahydrofurans and 2-substituted furans
  作者：Venu Srinivas、K.V. Sajna、K.C. Kumara Swamy

  DOI：10.1016/j.tetlet.2011.08.020

  日期：2011.10

  A novel synthesis of 2,5-dimethylenetetrahydrofurans, 2-substituted furans and a beta,omega-diketophosphonate in good to excellent yields has been achieved by the reaction of allenylphosphine oxides/allenylphosphonate with propargyl alcohol using zinc triflate/triethylamine combination. (C) 2011 Elsevier Ltd. All rights reserved.