3,5-Dibromo-4-iodobiphenyl | 135990-00-0

• 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: 3,5-Dibromo-4-iodobiphenyl
• 英文别名: 1,1'-Biphenyl, 3,5-dibromo-4-iodo-；1,3-dibromo-2-iodo-5-phenylbenzene
• CAS: 135990-00-0
• 化学式: C₁₂H₇Br₂I
• 分子量: 437.9
• InChiKey: KHSXOXKSILOGKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  3,5-Dibromo-4-iodobiphenyl 在 乙烯基溴化镁 、 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 3.08h， 生成 3,5-Bis<2-(bromomethyl)-6-methylphenyl>biphenyl
  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
• 作为产物：
  描述：

  4-氨基-3,5-二溴-1,1'-联苯 在 盐酸 、 potassium iodide 、 sodium nitrite 作用下， 生成 3,5-Dibromo-4-iodobiphenyl
  参考文献：
  名称：

  Synthesis of self-filled, vaulted, and intracavity functionalized cappedophanes

  摘要：

  Two approaches to the synthesis of vaulted cappedophanes 3v are described. In the first, the walls and ceiling were prefabricated as in tetrathiol 5 (10a and 10b, Scheme II, are specific examples), which was then coupled with a m-terphenyl tetrabromide such as 4. This route was most successful when the m-terphenyl base carried a large substituent (Ph, Br) in the 5' position. Thus tetrathiol 10a and tetrabromide 25 gave vaulted cappedophane 27v in good yield (Scheme VIII). In the absence of a 5' substituent, the major product was the self-filled conformer. For example, 10a and 4 gave mainly 11sf (62%) and only 2% of its vaulted conformer 11v (Scheme III), and tetrathiol 10b reacted with 4 to give (79%) only the self-filled conformer 15sf (Scheme IV). In the second approach, a cuppedophane with suitably functionalized walls was first constructed, and the cap was attached in a second step. For example, bisphenol 29, when coupled with p-xylylene dibromide, gave mainly vaulted conformer 11v (51%) and only a trace of 11sf (Scheme IX). Extension of this method to several other dihalides, however, gave mainly self-filled conformers (Schemes XI and XII) and even p-xylylene dibromide gave only self-filled product 33sf when the bisphenol contained a substituent at C2' of the m-terphenyl base (Scheme XIII). The reasons for the predominant formation of self-filled vis-a-vis vaulted cappedophane conformers are discussed. These studies open the way for the synthesis of vaulted cappedophanes containing functionality within the molecular cavity.

  DOI：

  10.1021/jo00019a032

文献信息

• Triplet Diphenylcarbenes Protected by <i>o</i>-Aryl Groups
  作者：Kyoko Monguchi、Tetsuji Itoh、Katsuyki Hirai、Hideo Tomioka

  DOI：10.1021/ja047738r

  日期：2004.9.1

  2a-N(2) in a 2-methyltetrahydrofuran (2-MTHF) matrix at 77 K gave ESR signals ascribable to triplet carbenes ((3)2a). UV/vis spectra of (3)2a were obtained by irradiating 2a-N(2) under identical conditions. However, laser flash photolysis (LFP) of 2a-N(2) in degassed benzene at room temperature showed transient absorption bands completely different from those observed in photolysis in the 2-MTHF matrix

  制备了在邻位具有苯基的二苯基重氮甲烷 (2a-N(2)) 并且从它们光解产生的相应二苯基卡宾 (2a) 不仅通过传统的产品分析方法而且通过 ESR 和紫外/可见光谱在一个低温下的刚性有机基质和室温下溶液中的激光闪光光解。产物分析表明芴4a 几乎完全形成。芴最有可能通过单线态卡宾 (1)2a 攻击苯基取代基的邻位碳生成异芴，然后发生 1,5-H 位移。2a-N(2) 在 2-甲基四氢呋喃 (2-MTHF) 矩阵中在 77 K 的辐照给 ESR 信号归因于三线态卡宾 ((3)2a)。(3)2a 的紫外/可见光谱是通过在相同条件下照射 2a-N(2) 获得的。然而，室温下脱气苯中 2a-N(2) 的激光闪光光解 (LFP) 显示瞬态吸收带与在 77 K 的 2-MTHF 基质中的光解中观察到的完全不同。瞬态吸收带在一阶衰减速率常数为 7.6 x 10(4) s(-1)，这不会因邻苯基氢的氘取代而延迟。在芴4a
• Synthesis of self-filled, vaulted, and intracavity functionalized cappedophanes
  作者：Thottumkara K. Vinod、Harold Hart

  DOI：10.1021/jo00019a032

  日期：1991.9

  Two approaches to the synthesis of vaulted cappedophanes 3v are described. In the first, the walls and ceiling were prefabricated as in tetrathiol 5 (10a and 10b, Scheme II, are specific examples), which was then coupled with a m-terphenyl tetrabromide such as 4. This route was most successful when the m-terphenyl base carried a large substituent (Ph, Br) in the 5' position. Thus tetrathiol 10a and tetrabromide 25 gave vaulted cappedophane 27v in good yield (Scheme VIII). In the absence of a 5' substituent, the major product was the self-filled conformer. For example, 10a and 4 gave mainly 11sf (62%) and only 2% of its vaulted conformer 11v (Scheme III), and tetrathiol 10b reacted with 4 to give (79%) only the self-filled conformer 15sf (Scheme IV). In the second approach, a cuppedophane with suitably functionalized walls was first constructed, and the cap was attached in a second step. For example, bisphenol 29, when coupled with p-xylylene dibromide, gave mainly vaulted conformer 11v (51%) and only a trace of 11sf (Scheme IX). Extension of this method to several other dihalides, however, gave mainly self-filled conformers (Schemes XI and XII) and even p-xylylene dibromide gave only self-filled product 33sf when the bisphenol contained a substituent at C2' of the m-terphenyl base (Scheme XIII). The reasons for the predominant formation of self-filled vis-a-vis vaulted cappedophane conformers are discussed. These studies open the way for the synthesis of vaulted cappedophanes containing functionality within the molecular cavity.
• 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.