2-iodo-1,1':4',1''-terphenyl | 76129-24-3

• 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: 2-iodo-1,1':4',1''-terphenyl
• 英文别名: 2-Iodo-1,1a(2):4a(2),1a(2)a(2)-terphenyl；1-iodo-2-(4-phenylphenyl)benzene
• CAS: 76129-24-3
• 化学式: C₁₈H₁₃I
• 分子量: 356.206
• InChiKey: UCVPLJBRQBRGRL-UHFFFAOYSA-N

物化性质

• 熔点：
  100 °C(Solv: ligroine (8032-32-4))
• 沸点：
  217-218 °C(Press: 5 Torr)
• 密度：
  1.471±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• 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：

  2-iodo-1,1':4',1''-terphenyl 在 三氟甲磺酸 、 copper diacetate 、 sodium carbonate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 乙二醇 、 异丙醇 为溶剂， 反应 17.0h， 生成 2-phenyl-9-tosyl-9H-carbazole
  参考文献：
  名称：

  Discovery of novel N-substituted carbazoles as neuroprotective agents with potent anti-oxidative activity

  摘要：

  Carbazole moiety is an important scaffold with a variety of biological applications, for example, anti-oxidative stress. Our previous synthesized carbazoles were screened for their neuroprotective properties against two individual oxidative stresses. Some of the new carbazole derivatives were observed with modest to good neuroprotective effects on neuronal cells HT22 against cell injury induced by glutamate or homocysteic acid (HCA). Substituents introduced to the carbazole ring system play crucial roles in their biological activities. In particular, a bulky group favors the neuroprotective activity of the compounds. One of the new compounds, 6, showed the best neuroprotective effects, which might result from its anti-oxidative activity with a GSH-independent mechanism. These findings might provide an alternative strategy for the development of novel carbazole derivatives for the treatment of CNS diseases such as Alzheimer's disease. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.07.029
• 作为产物：
  描述：

  4-联苯硼酸 在 盐酸 、 palladium diacetate 、 potassium carbonate 、 sodium nitrite 作用下， 以 水 、 丙酮 为溶剂， 反应 1.0h， 生成 2-iodo-1,1':4',1''-terphenyl
  参考文献：
  名称：

  钯催化双CC键形成2-碘代联苯和CH 2 Br 2的芴合成

  摘要：

  开发了一种简便有效的方法来合成芴及其衍生自2-碘联苯和CH 2 Br 2的衍生物。可以在相对温和的条件下合成一系列芴衍生物。反应是通过关键的二苯并钯铝环戊二烯中间体，通过串联的钯催化的双C–C键形成序列进行的，该中间体是通过钯催化的C–H活化作用从2-碘代联苯中获得的。

  DOI：

  10.1021/acs.orglett.6b01300

文献信息

• Palladium-Catalyzed C−H Silylation through Palladacycles Generated from Aryl Halides
  作者：Ailan Lu、Xiaoming Ji、Bo Zhou、Zhuo Wu、Yanghui Zhang

  DOI：10.1002/anie.201800330

  日期：2018.3.12

  A highly efficient palladium‐catalyzed disilylation reaction of aryl halides through C−H activation has been developed for the first time. The reaction has broad substrate scope. A variety of aryl halides can be disilylated by three types of C−H activation, including C(sp2)−H, C(sp3)−H, and remote C−H activation. In particular, the reactions are also unusually efficient. The yields are essentially

  首次开发了通过CH活化的高效钯催化的芳基卤化物的二甲硅烷基化反应。该反应具有广泛的底物范围。多种芳基卤化物可通过三种类型的CH活化来二芳基化，包括C（sp 2）-H，C（sp 3）-H和远程CHH活化。特别地，反应也异常有效。在许多情况下，即使在相对温和的条件下，即使存在少于1摩尔％的催化剂和1当量的甲硅烷基化试剂，收率也基本上是定量的。可以将二甲硅烷基化的联苯转化为二硅氧烷桥联的联苯。
• Synthesis of 9-Fluorenylidenes via Pd-Catalyzed C–H Vinylation with Vinyl Bromides
  作者：Shuai Yang、Yanghui Zhang

  DOI：10.1021/acs.orglett.1c02722

  日期：2021.10.15

  A facile and efficient approach for the synthesis of 9-fluorenylidenes has been developed via the palladium-catalyzed cross-coupling of 2-iodobiphenyls and vinyl bromides. The reaction involves the C–H activation of 2-iodobiphenyls and dual C–C bond formations. A range of 9-fluorenylidene derivatives, including diphenyldibenzofulvenes, can be synthesized with the reaction.

  通过钯催化的 2-碘联苯和乙烯基溴的交叉偶联，开发了一种简便有效的合成 9-芴基的方法。该反应涉及 2-碘联苯的 C-H 活化和双 C-C 键的形成。通过该反应可以合成一系列 9-芴基衍生物，包括二苯基二苯并富烯。
• Palladium-catalyzed coupling reaction of 2-iodobiphenyls with alkenyl bromides for the construction of 9-(diorganomethylidene)fluorenes
  作者：Ya-Heng Zhao、Jian-Long Wang、Yun-Bing Zhou、Miao-Chang Liu、Hua-Yue Wu

  DOI：10.1039/d1ob01547h

  日期：——

  protocol for the construction of 9-(diorganomethylidene)fluorenes through palladium-catalyzed coupling reactions of 2-iodobiphenyls with alkenyl bromides has been reported. The reaction proceeds through the C–H activation/oxidative addition/reduction elimination/intramolecular Heck coupling reaction to afford a series of 9-(diorganomethylidene)fluorenes with good yields. Control experiments demonstrate that

  已经报道了通过钯催化的 2-碘联苯与烯基溴的偶联反应构建 9-（二有机亚甲基）芴的原子经济协议。该反应通过C-H活化/氧化加成/还原消除/分子内Heck偶联反应进行，以良好的收率得到一系列9-(二有机亚甲基)芴。对照实验表明，五元钯环作为关键中间体，β-H 消除作为限速步骤。
• Palladium-Catalyzed C–H Amination/[2 + 3] or [2 + 4] Cyclization via C(sp³ or sp²)–H Activation
  作者：Yang An、Yuke Li、Xiao-Yan Zhang、Zhe Zhang、Xue-Ya Gou、Ya-Nan Ding、Qiao Li、Yong-Min Liang

  DOI：10.1021/acs.orglett.1c02964

  日期：2021.10.15

  This report describes a palladium-catalyzed Catellani reaction consisting of amination/[2 + 3] or [2 + 4] cyclization via a carboxylate ligand-exchange strategy. This method effectively activates ortho-substituents that avoid a second C–H palladation. The scope of substrates was broad, o-methyl-substituted iodoarenes were applied to the reaction smoothly, and o-phenyl-substituted iodoarenes can also

  本报告描述了钯催化的 Catellani 反应，该反应由通过羧酸盐配体交换策略的胺化/[2 + 3] 或 [2 + 4] 环化组成。这种方法有效地激活了避免第二次 C–H 钯化的邻位取代基。底物范围广，邻甲基取代的碘芳烃适用于反应顺利，该方法也可以得到邻苯基取代的碘芳烃。在机理方面，密度泛函理论计算证明了关键的五元芳基-降冰片烯-钯环中间体形成和C(sp 3或sp 2 )-H活化的顺序。
• Conversion of 2-Iodobiaryls into 2,2′-Diiodobiaryls via Oxidation-Iodination Sequences: A Versatile Route to Ladder-Type Heterofluorenes
  作者：Bin Wu、Naohiko Yoshikai

  DOI：10.1002/anie.201503134

  日期：2015.7.20

  heterofluorenes and other extended π‐conjugated systems, their preparation still remains nontrivial when structural diversity of the biaryl backbone is required. Herein, we report a convenient method for the preparation of various 2,2′‐diiodobiaryls from 2‐iodobiaryls via cyclic diaryliodonium intermediates. An iodinative ring‐opening of the diaryliodonium salts, mediated by a copper/diamine catalyst

  尽管2,2'-二碘代和2,2'-二溴代双芳基代表了杂芴和其他扩展的π-共轭体系的成功前体，但是当需要联芳基骨架的结构多样性时，它们的制备仍然很重要。在这里，我们报告了一种方便的方法，可以通过环二芳基碘鎓中间体从2-碘二联芳基制备各种2,2'-二碘联二芳基。在铜/二胺催化剂体系的介导下，二芳基碘鎓盐的碘化开环能够在温和的条件下提供相应的2,2'-二碘二联芳基。迄今未开发的四碘杂芳基化合物的制备及其转化为梯型π共轭体系证明了这种两步法的多功能性。