1-(2-bromophenyl)-2-phenylcyclopropane | 206345-97-3

• 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-(2-bromophenyl)-2-phenylcyclopropane
• 英文别名: 1-Bromo-2-(2-phenylcyclopropyl)benzene；1-bromo-2-(2-phenylcyclopropyl)benzene
• CAS: 206345-97-3
• 化学式: C₁₅H₁₃Br
• 分子量: 273.172
• InChiKey: WBJPGFUNRRQHTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 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-(2-bromophenyl)-2-phenylcyclopropane 在 N-甲基吡咯烷酮 、 溶剂黄146 作用下， 反应 24.0h， 生成
  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
• 作为产物：
  描述：

  苯乙酮 、 邻溴苯甲醛 生成 1-(2-bromophenyl)-2-phenylcyclopropane
  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

• Asymmetric Radical Cyclopropanation of Alkenes with In Situ-Generated Donor-Substituted Diazo Reagents via Co(II)-Based Metalloradical Catalysis
  作者：Yong Wang、Xin Wen、Xin Cui、Lukasz Wojtas、X. Peter Zhang

  DOI：10.1021/jacs.6b11336

  日期：2017.1.25

  Donor-substituted diazo reagents, generated in situ from sulfonyl hydrazones in the presence of base, can serve as suitable radical precursors for Co(II)-based metalloradical catalysis (MRC). The cobalt(II) complex of D2-symmetric chiral porphyrin [Co(3,5-DitBu-Xu(2'-Naph)Phyrin)] is an efficient metalloradical catalyst that is capable of activating different N-arylsulfonyl hydrazones for asymmetric radical

  在碱存在下由磺酰腙原位生成的供体取代的重氮试剂可以作为 Co(II) 基金属自由基催化 (MRC) 的合适自由基前体。 D2-对称手性卟啉的钴(II)络合物[Co(3,5-DitBu-Xu(2'-Naph)Phyrin)]是一种有效的金属自由基催化剂，能够活化不同的N-芳基磺酰腙进行不对称自由基环丙烷化广泛的烯烃，以高产率提供相应的环丙烷，并有效控制非对映选择性和对映选择性。这种基于 Co(II) 的金属自由基体系代表了第一个可以有效利用供体型重氮试剂进行不对称烯烃环丙烷化的催化方案。
• 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.