(E)-4,4'-(prop-1-ene-1,3-diyl)bis(acetophenone)

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-4,4'-(prop-1-ene-1,3-diyl)bis(acetophenone)
• 英文别名: (E)-1,3-bis(4-acetylphenyl)propene；1-[4-[(E)-3-(4-acetylphenyl)prop-2-enyl]phenyl]ethanone
• 化学式: C₁₉H₁₈O₂
• 分子量: 278.351
• InChiKey: CUPGGWIXVZZEMI-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,2-二苯基环丙烷 在 三氯化铝 作用下， 以 二硫化碳 、 苯 为溶剂， 反应 56.0h， 生成 (E)-4,4'-(prop-1-ene-1,3-diyl)bis(acetophenone)
  参考文献：
  名称：

  Photochemical C−C Bond Cleavage of 1,2-Diarylcyclopropanes Bearing an Acetylphenyl Group. Generation and Observation of Triplet 1,3-Biradicals

  摘要：

  The photochemical properties of 1,2-diarylcyclopropanes bearing an acetylphenyl group were studied by product analysis and laser flash photolysis. All cyclopropanes showed efficient cis-trans photoisomerization followed by inefficient isomerization to 1,3-diarylpropenes. All the products were unquenched by the addition of triplet quencher, 2-methyl-1,3-butadiene (E-T similar or equal to 60 kcal mol(-1)), whereas molecular dioxygen gave oxygenated products. Triplet 1,3-biradicals generated from a short-lived acetophenone-like triplet (less than or similar to 1 ns) were observed as intermediates in these reactions through nanosecond laser flash photolysis. Polar substituent effects on the lifetime of the 1,3-biradicals were small, except for a heavy atom effect in the case of Br. Spin-orbit coupling calculations on model 1,3-biradicals show a negligible effect on polar substituent and thus predict a negligible effect on the intersystem crossing rate. Conjugated biradicals in general now seem unlikely to show the "ionic character effect" on intersystem crossing suggested by the work of Salem and Rowland.

  DOI：

  10.1021/jo971111s

文献信息

• Palladium-Catalyzed Heck-Type Reactions of Allylic Esters with Arylboronic Acids or Potassium Aryltrifluoroborates
  作者：Bo Yao、Yan Liu、Meng-Ke Wang、Jin-Heng Li、Ri-Yuan Tang、Xing-Guo Zhang、Chen-Liang Deng

  DOI：10.1002/adsc.201100889

  日期：2012.4.16

  A selective and general route to (E)‐1,3‐diaryl‐prop‐1‐enes and (E)‐3‐arylallyl acetates has been developed by palladium‐catalyzed Heck‐type reactions of allylic esters with arylboronic acids or potassium aryltrifluoroborates. The present method selectively proceeds including β‐OAc elimination or β‐H elimination on the basis of the boronic acids. Whereas a variety of allylic esters were reacted with

  通过钯催化的烯丙基酯与芳基硼酸或芳基三氟硼酸钾的Heck型反应，已经开发出一种选择性的通用路线来制备（E）-1,3-二芳基丙-1-烯和（E）-3-芳基乙酸烯丙酯。本方法选择性地进行，包括基于硼酸的β-OAc消除或β-H消除。各种烯丙基酯与芳基硼酸，乙酸钯（II）[Pd（OAc）2 ]，四正丁基氯化铵[（n -Bu）4 NCl]和磷酸二氢钾（KH 2 PO）反应4）以中等至良好的产率得到相应的二芳基化产物，用芳基三氟硼酸钾处理烯丙基酯得到相应的单芳基化产物。
• Palladium-Catalyzed Selective Heck-Type Diarylation of Allylic Esters with Aryl Halides Involving a β-OAc Elimination Process
  作者：Yan Liu、Bo Yao、Chen-Liang Deng、Ri-Yuan Tang、Xing-Guo Zhang、Jin-Heng Li

  DOI：10.1021/ol1031552

  日期：2011.3.4

  Palladium-catalyzed selective Heck-type diarylation of allylic esters with aryl halides has been developed. Allylic esters are reacted with aryl iodides to provide the corresponding 1,3-diaryl propenes through a β-OAc elimination process. It is noteworthy that the methodology can be applied in constructing the indole and benzofuran skeletons.

  已经开发了钯催化的烯丙基酯与芳基卤化物的选择性Heck型二芳基化。使烯丙酸酯与芳基碘化物通过β-OAc消除过程提供相应的1，3-二芳基丙烯。值得注意的是，该方法可用于构建吲哚和苯并呋喃的骨架。
• Direct observation of a 1,3-biradical
  作者：K. Mizuno、N. Ichinose、Y. Otsuji

  DOI：10.1021/ja00306a034

  日期：1985.10

  Observation d'un diradical diaryl-1,3 propanediyle au cours de la photolyse du trans-bis-(acetyl-4' phenyl)-1,2cyclopropane et du trans-[acetyl-4' phenyl]-1 phenyl-2 cyclopropane

  Observation d'un diradical diaryl-1,3 propanediyle au cours de la photolyse du trans-bis-(acetyl-4' phenyl)-1,2cyclopropane et du trans-[acetyl-4' phenyl]-1 phenyl-2 cyclopropane
• Photochemical C−C Bond Cleavage of 1,2-Diarylcyclopropanes Bearing an Acetylphenyl Group. Generation and Observation of Triplet 1,3-Biradicals
  作者：Nobuyuki Ichinose、Kazuhiko Mizuno、Yoshio Otsuji、Richard A. Caldwell、Anna M. Helms

  DOI：10.1021/jo971111s

  日期：1998.5.1

  The photochemical properties of 1,2-diarylcyclopropanes bearing an acetylphenyl group were studied by product analysis and laser flash photolysis. All cyclopropanes showed efficient cis-trans photoisomerization followed by inefficient isomerization to 1,3-diarylpropenes. All the products were unquenched by the addition of triplet quencher, 2-methyl-1,3-butadiene (E-T similar or equal to 60 kcal mol(-1)), whereas molecular dioxygen gave oxygenated products. Triplet 1,3-biradicals generated from a short-lived acetophenone-like triplet (less than or similar to 1 ns) were observed as intermediates in these reactions through nanosecond laser flash photolysis. Polar substituent effects on the lifetime of the 1,3-biradicals were small, except for a heavy atom effect in the case of Br. Spin-orbit coupling calculations on model 1,3-biradicals show a negligible effect on polar substituent and thus predict a negligible effect on the intersystem crossing rate. Conjugated biradicals in general now seem unlikely to show the "ionic character effect" on intersystem crossing suggested by the work of Salem and Rowland.