4-氯-1,2-二碘苯 | 1608-45-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-氯-1,2-二碘苯
• 英文名称: 4-chloro-1,2-diiodobenzene
• CAS: 1608-45-3
• 化学式: C₆H₃ClI₂
• 分子量: 364.352
• InChiKey: WOTDERBDCYWTRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• 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

安全信息

• 海关编码：
  2903999090

反应信息

• 作为反应物：
  描述：

  4-氯-1,2-二碘苯 在 sodium azide 、 碘 、 异丙基氯化镁 、 次磷酸 、 溶剂黄146 、 间氯过氧苯甲酸 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基乙酰胺 、 水 为溶剂， 反应 50.0h， 生成 7-chloro-1-methylacridine
  参考文献：
  名称：

  Nitrogen–Iodine Exchange of Diaryliodonium Salts: Access to Acridine and Carbazole

  摘要：

  A nitrogen iodine exchange protocol of diaryliodonium salts with sodium azide salt is developed for general construction of significant functional acridines and carbazoles, in which introduction of nitrogen at a late stage was successfully established avoiding heteroatom incompatibility. Inorganic sodium azide served as the sole nitrogen atom source in this transformation. The diversiform functional acridines and carbazoles were comprehensively achieved through annulated diaryliodonium salts, respectively. Notably, Acridine orange (a fluorescent indicator for cell lysosomal dye) and Carprofen (a non steroidal anti-inflammatory drug) were efficiently established through this protocol.

  DOI：

  10.1021/acs.orglett.7b03564
• 作为产物：
  描述：

  2-氨基-5-氯苯甲酸 在 碘 、 亚硝酸异戊酯 作用下， 以 1,4-二氧六环 、 氘代氯仿 为溶剂， 反应 18.0h， 生成 4-氯-1,2-二碘苯
  参考文献：
  名称：

  Preparation of N-substituted phthalimides by the palladium-catalyzed carbonylation and coupling of o-dihalo aromatics and primary amines

  摘要：

  A novel method for the formation of N-substituted phthalimides is described which is based on the palladium-catalyzed carbonylation and coupling of o-dihalo aromatics and primary amines. Optimal conditions established for the reaction using o-diiodobenzene and aniline were DMAc (0.2 M), 115-degrees-C, 90 psi of CO, 3% PdCl2L2, and 2.4 equiv of DBU. This process is tolerant of a wide variety of functional groups and gives good yields of the desired products. Variables such as temperature, catalyst type and loading, CO pressure, solvent, and base were examined to optimize this reaction. The reaction of aniline with 1,2-dibromocyclopentene under similar conditions gave a variety of products.

  DOI：

  10.1021/jo00023a023

文献信息

• Efficient and Regioselective Synthesis of Phenothiazine via Ferric Citrate Catalyzed C-S/C-N Cross-Coupling
  作者：Tonmoy Chitta Das、Syed Aziz Imam Quadri、Mazahar Farooqui

  DOI：10.2174/1570178615666180806114523

  日期：2018.12.4

  Efficient C-S and C-N cross-coupling reactions have been developed for regioselective, scalable and environmentally benign synthesis of substituted phenothiazine derivatives. Cross-coupling reactions were demonstrated on various challenging substrates using non-toxic, highly economical, readily available ferric citrate as a catalyst to get desired product with high regioselectivity. Atom economy is

  已经开发出有效的CS和CN交叉偶联反应，用于取代的吩噻嗪衍生物的区域选择性，可扩展性和环境友好的合成。使用无毒，经济性强，易得的柠檬酸铁作为催化剂，可以在各种具有挑战性的底物上进行交叉偶联反应，从而获得具有高区域选择性的所需产物。原子经济性是该协议的另一个优点，因为不需要在耦合之前进行额外的N保护步骤以及最终对其进行脱保护以获得所需产品的步骤。据我们所知，这是关于使用廉价的柠檬酸铁作为催化剂而不涉及任何配体来合成区域选择性取代的吩噻嗪的报道。
• Method for the Synthesis of Phenothiazines via a Domino Iron-Catalyzed C–S/C–N Cross-Coupling Reaction
  作者：Weiye Hu、Songlin Zhang

  DOI：10.1021/acs.joc.5b00568

  日期：2015.6.19

  An environmentally benign and efficient method has been developed for the synthesis of phenothiazines via a tandem iron-catalyzed C–S/C-N cross-coupling reaction. Some of the issues typically encountered during the synthesis of phenothiazines in the presence of palladium and copper catalysts, including poor substrate scope, long reaction times and poor regioselectivity, have been addressed using this

  通过串联铁催化的C-S / CN交叉偶联反应，已开发出一种环境友好，高效的方法来合成吩噻嗪。使用这种新开发的铁催化方法已经解决了在存在钯和铜催化剂的情况下吩噻嗪合成过程中通常遇到的一些问题，包括较差的底物范围，较长的反应时间和较差的区域选择性。
• Improved Synthesis of 1,2-Bis(trimethylsilyl)benzenes using Rieke-Magnesium or the Entrainment Method
  作者：Andreas Lorbach、Christian Reus、Michael Bolte、Hans-Wolfram Lerner、Matthias Wagner

  DOI：10.1002/adsc.201000560

  日期：2010.12.17

  that the cancerogenic solvent hexamethylphosphoramide is avoided. Moreover, the improved protocols are also applicable for the high-yield synthesis of 1,2,4,5-tetrakis(trimethylsilyl)benzene, 4-fluoro-1,2-bis(trimethylsilyl)benzene, 4-chloro-1,2-bis(trimethylsilyl)benzene, and 4,5-dichloro-1,2-bis(trimethylsilyl)benzene.

  1,2-双（三甲基甲硅烷基）苯是合成高效苯炔前体和某些发光的π共轭材料的关键原料。我们现在报道，它可以在1,2-二溴乙烷作为夹带剂（Mg e）的情况下，方便地在四氢呋喃中由1,2-二溴苯，三甲基氯硅烷和Rieke-镁（Mg R）或镁车削制备。这些新方法相对于目前最完善的方法（1,2-二氯苯，氯三甲基硅烷，镁屑，六甲基磷酰胺）的最重要优势在于反应条件温和（Mg R：0°C，2 h； Mg e：室温温度，相对于30分钟100°C，2天），并且应避免使用致癌溶剂六甲基磷酰胺。而且，改进的方案也适用于高产率合成1,2,4,5-四（三甲基甲硅烷基）苯，4-氟-1,2-双（三甲基甲硅烷基）苯，4-氯-1,2 -双（三甲基甲硅烷基）苯和4,5-二氯-1,2-双（三甲基甲硅烷基）苯。
• C1−C5 Photochemical Cyclization of Enediynes
  作者：Igor V. Alabugin、Serguei V. Kovalenko

  DOI：10.1021/ja026630d

  日期：2002.8.1

  This study reports a new photochemical cyclization of tetrafluoropyridinyl (TFP)-substituted enediynes that is accompanied with four formal hydrogen-atom abstractions from organic substrates and is mechanistically different from the Bergman cyclization.

  这项研究报告了四氟吡啶基 (TFP) 取代的烯二炔的一种新的光化学环化，伴随着从有机底物的四个正式的氢原子提取，并且在机械上与伯格曼环化不同。
• Synthesis of benzoxazoles <i>via</i> an iron-catalyzed domino C–N/C–O cross-coupling reaction
  作者：Bo Yang、Weiye Hu、Songlin Zhang

  DOI：10.1039/c7ra13080e

  日期：——

  An eco-friendly and efficient method has been developed for the synthesis of 2-arylbenzoxazoles via a domino iron-catalyzed C–N/C–O cross-coupling reaction. Some of the issues typically encountered during the synthesis of 2-arylbenzoxazoles in the presence of palladium and copper catalysts, including poor substrate scope and long reaction times have been addressed using this newly developed iron-catalyzed

  开发了一种通过多米诺铁催化的 C-N/C-O 交叉偶联反应合成 2-芳基苯并恶唑的环保高效方法。使用这种新开发的铁催化方法已经解决了在钯和铜催化剂存在下合成 2-芳基苯并恶唑的过程中通常遇到的一些问题，包括底物范围差和反应时间长。