cis-1,2-bis(4-acetylphenyl)cyclopropane | 97974-87-3

• 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: cis-1,2-bis(4-acetylphenyl)cyclopropane
• 英文别名: 1-[4-[(1S,2R)-2-(4-acetylphenyl)cyclopropyl]phenyl]ethanone
• CAS: 97974-87-3
• 化学式: C₁₉H₁₈O₂
• 分子量: 278.351
• InChiKey: NPJAVQIKKFJGLQ-KDURUIRLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cis-1,2-bis(4-acetylphenyl)cyclopropane 以 二乙二醇 为溶剂， 反应 2.0h， 生成 trans-1,2-bis(4-acetylphenyl)cyclopropane
  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：

  1,2-二苯基环丙烷 在 bis-triphenylphosphine-palladium(II) chloride N-溴代丁二酰亚胺(NBS) 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 71.0h， 生成 cis-1,2-bis(4-acetylphenyl)cyclopropane
  参考文献：
  名称：

  [EN] HEPATITIS C VIRUS INHIBITORS
  [FR] INHIBITEURS DU VIRUS DE L'HÉPATITE C

  摘要：

  这项披露涉及到规范中定义的Formula (I)的新化合物以及包含这些新化合物的组合物。这些化合物是有用的抗病毒剂，特别是在抑制由丙型肝炎病毒（HCV）编码的NS5A蛋白的功能方面。因此，该披露还涉及通过使用这些新化合物或包含这些新化合物的组合物来治疗HCV相关疾病或症状的方法。

  公开号：

  WO2012039717A1

文献信息

• [EN] HEPATITIS C VIRUS INHIBITORS<br/>[FR] INHIBITEURS DU VIRUS DE L'HÉPATITE C
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2012039717A1

  公开（公告）日：2012-03-29

  This disclosure concerns novel compounds of Formula (I) as defined in the specification and compositions comprising such novel compounds. These compounds are useful antiviral agents, especially in inhibiting the function of the NS5A protein encoded by Hepatitis C virus (HCV). Thus, the disclosure also concerns a method of treating HCV related diseases or conditions by use of these novel compounds or a composition comprising such novel compounds.

  这项披露涉及到规范中定义的Formula (I)的新化合物以及包含这些新化合物的组合物。这些化合物是有用的抗病毒剂，特别是在抑制由丙型肝炎病毒（HCV）编码的NS5A蛋白的功能方面。因此，该披露还涉及通过使用这些新化合物或包含这些新化合物的组合物来治疗HCV相关疾病或症状的方法。
• 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
• Shabarov,Yu.S. et al., Journal of Organic Chemistry USSR (English Translation), 1966, vol. 2, p. 2111 - 2115
  作者：Shabarov,Yu.S. et al.

  DOI：——

  日期：——
• 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.