9,10-Dihydro-5,14-dimethyl2-2phenyltribenzocyclooctene | 137300-39-1

• 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: 9,10-Dihydro-5,14-dimethyl2-2phenyltribenzocyclooctene
• 英文别名: 9,20-Dimethyl-4-phenyltetracyclo[14.4.0.02,7.08,13]icosa-1(20),2(7),3,5,8,10,12,16,18-nonaene
• CAS: 137300-39-1
• 化学式: C₂₈H₂₄
• 分子量: 360.499
• InChiKey: RLVJHLLNZALOMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  4-氨基-3,5-二溴-1,1'-联苯 在 硫酸 、 乙烯基溴化镁 、 三溴化硼 、 苯基锂 、 potassium iodide 、 sodium nitrite 作用下， 以 乙醚 、 二氯甲烷 、 环己烷 为溶剂， 反应 25.83h， 生成 9,10-Dihydro-5,14-dimethyl2-2phenyltribenzocyclooctene
  参考文献：
  名称：

  Photoisomerization of 2,2''-ethano-bridged m-terphenyl derivatives: ring constraint activates an unreactive chromophore

  摘要：

  The photochemistry of 2,2''-ethano-bridged m-terphenyl derivatives 4, 8, and 9 was investigated. These compounds are chiral and may be suitable photoresolvable additives to discotic liquid crystals. Unlike their unbridged analogues, 4, 8, and 9 rearrange rapidly when irradiated with UV light to the o-terphenyl compounds 10, 11, and 12, respectively. This rearrangement is likely to proceed through an intermediate benzvalene valence-bond isomer. The high reactivity of the 2,2''-ethano-bridged compounds is attributed to distortion in their lowest excited singlet states and to the relief of strain when the ortho isomers are formed.

  DOI：

  10.1021/jo00027a059

文献信息

• Photoisomerization of 2,2''-ethano-bridged m-terphenyl derivatives: ring constraint activates an unreactive chromophore
  作者：B. S. Udayakumar、Gary B. Schuster

  DOI：10.1021/jo00027a059

  日期：1992.1

  The photochemistry of 2,2''-ethano-bridged m-terphenyl derivatives 4, 8, and 9 was investigated. These compounds are chiral and may be suitable photoresolvable additives to discotic liquid crystals. Unlike their unbridged analogues, 4, 8, and 9 rearrange rapidly when irradiated with UV light to the o-terphenyl compounds 10, 11, and 12, respectively. This rearrangement is likely to proceed through an intermediate benzvalene valence-bond isomer. The high reactivity of the 2,2''-ethano-bridged compounds is attributed to distortion in their lowest excited singlet states and to the relief of strain when the ortho isomers are formed.