2-Jodo-4-chloro-thiophenol | 62835-70-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚类
• 英文名称: 2-Jodo-4-chloro-thiophenol
• 英文别名: 4-chloro-2-iodothiophenol；4-Chloro-2-iodobenzenethiol
• CAS: 62835-70-5
• 化学式: C₆H₄ClIS
• 分子量: 270.521
• InChiKey: IVGUVBBHSNYGHA-UHFFFAOYSA-N

物化性质

• 沸点：
  286.5±25.0 °C(Predicted)
• 密度：
  1.988±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 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：
  1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-Jodo-4-chloro-thiophenol 在 sodium hydroxide 、 氢溴酸 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 生成 2'-Jodo-4'-chloro-2-nitro-4,5-dihydroxy-diphenylsulfid
  参考文献：
  名称：

  Lee,F.G.H. et al., Journal of Heterocyclic Chemistry, 1972, vol. 9, p. 387 - 392

  摘要：

  DOI：
• 作为产物：
  描述：

  2-碘-4-氯苯胺 在 盐酸 、 氢氧化钾 、 sodium nitrite 作用下， 以 乙醇 为溶剂， 反应 11.0h， 生成 2-Jodo-4-chloro-thiophenol
  参考文献：
  名称：

  Regioselective Carbonylative Heteroannulation of o-Iodothiophenols with Allenes and Carbon Monoxide Catalyzed by a Palladium Complex:  A Novel and Efficient Access to Thiochroman-4-one Derivatives

  摘要：

  The palladium-catalyzed carbonylative ring-forming reactions of 2-iodothiophenol, and the corresponding substituted derivatives, with allenes and carbon monoxide are described. The reactions afford thiochroman-4-ones in good to excellent isolated yields with quite high regioselectivity. The catalytic heteroannulation may involve regioselective addition of the sulfur moiety of the reactants on the more positive end of the allene, arylpalladium formation, CO insertion, subsequent intramolecular cyclization, and then reductive elimination. The regioselectivity is probably governed by electronic effects.

  DOI：

  10.1021/jo9913098

文献信息

• Synthesis of 2-substituted benzo[b]thiophene via a Pd-catalyzed coupling of 2-iodothiophenol with phenylacetylene
  作者：Jingwen Chen、Haifeng Xiang、Li Yang、Xiangge Zhou

  DOI：10.1039/c6ra26611h

  日期：——

  2-iodothiophenol and phenylacetylene has been developed. A series of 2-substituted benzo[b]thiophenes were obtained in moderate to good yield (up to 87%). The application of this method was demonstrated by the synthesis of 2-(4-(tert-butyl)phenyl)benzo[b]thiophene 1,1-dioxide and (4-methoxyphenyl)(2-(4-methoxyphenyl)benzo[b]thiophen-3-yl)methanone, which exhibit a fluorescence quantum yield of up to 1 and

  已经开发了Pd（II）催化的2-碘硫代苯酚和苯乙炔之间的Sonogashira型交叉偶联反应。以中等至良好的产率（高达87％）获得了一系列2-取代的苯并[ b ]噻吩。该方法的应用程序是由2-（4-（合成证明叔丁基）苯基）苯并[ b ]噻吩-1,1-二氧化物和（4-甲氧基苯基）（2-（4-甲氧基苯基）苯并[ b ]噻吩-3-基）甲酮，其荧光量子产率最高为1，可以分别用作大麻素受体配体。
• The synthesis of possible hydroxylated metabolites of 2-chlorophenothiazine derivatives
  作者：Aija Zirnis、Joseph K. Suzuki、Donald E. Dickson、Robert A. Laitar、Albert A. Manian

  DOI：10.1002/jhet.5570140121

  日期：1977.2

  The synthesis of 7-hydroxy, 8-hydroxy and 7,8-dihydroxy prochlorperazines (3a) and per-phenazines (3b) is reported. The parent ehlorophenothiazines were prepared analogously to previously reported chlorpromazine (3e) metabolite syntheses. The prochlorperazine side chain was introduced in one step using 1-(3-chloropropyl)-4-methylpiperazine and the perphenazine side chain in two steps, first reaction

  报道了7-羟基，8-羟基和7,8-二羟基丙氯嗪（3a）和过吩嗪（3b）的合成。与先前报道的氯丙嗪（3e）代谢产物合成类似地制备母体埃洛洛吩噻嗪。使用1-（3-氯丙基）-4-甲基哌嗪和二氮杂吩嗪侧链分两步引入氯丙嗪侧链，首先与1-溴-3-氯丙烷反应，然后与1-哌嗪乙醇反应。在温和条件下，使用甲醇氯化氢除去甲氧基亚甲氧基的O-保护基。还报道了7-羟基去甲基丙氯嗪和7-羟基氯丙嗪季甲基碘的制备。
• Palladium-Catalyzed Domino Ring-Opening/Carboxamidation Reactions of <i>N</i>-Tosyl Aziridines and 2-Iodothiophenols: A Facile and Efficient Approach to 1,4-Benzothiazepin-5-ones
  作者：Fanlong Zeng、Howard Alper

  DOI：10.1021/ol102394h

  日期：2010.12.3

  A novel and efficient domino procedure has been developed for the synthesis of 1,4-benzothiazepin-5-ones from simple and readily accessible N-tosyl aziridines and o-iodothiophenols. This process involves aziridines ring-opening with o-iodothiophenols, followed by palladium-catalyzed intramolecular carboxamidation. The scope and limitation of this transformation have been investigated in detail by using

  已经开发了新颖且有效的多米诺方法，用于从简单且容易获得的N-甲苯磺酰基氮丙啶和邻碘硫代苯酚合成1,4-苯并噻唑啉-5-酮。该过程涉及用邻碘碘苯酚使氮丙啶开环，然后进行钯催化的分子内羧酰胺化。已经通过使用各种氮丙啶和邻碘硫代苯酚详细研究了这种转化的范围和局限性。
• [bmIm]OH catalyzed coupling: Green and efficient synthesis of 2,8 dioxacyclopenta [ a ] inden-3-one derivatives in an aqua media
  作者：Malik A Waseem、Shireen、Khursheed Ansari、Farah Ibad、Afshan Ibad、Jagdamba Singh、I.R. Siddiqui

  DOI：10.1016/j.tetlet.2017.09.039

  日期：2017.11

  protocol has documented the notable advances and the applications of ionic liquid in heterocyclic synthesis. The chosen strategy illustrates important issues regarding scope, reactivity, product yield, reaction time, reuse and recyclability that will help in designing new synthetic routes for other heterocyclic synthesis.

  一种有效的可循环利用的[bmIm] OH催化和水介导的生物通用2,8二氧杂环戊环[ a ] inden-3-one衍生物的水相容性生态相容性合成。离子液体和水的结合已成为构建C–C，C–S和C–O键的强大合成工具。在碱性离子液体中以可预见的高产率引入广泛的2-碘苯酚，2-碘硫代苯酚和tetronic酸的公开方法将引起合成化学家的关注。该方案记录了离子液体在杂环合成中的显着进展和应用。选择的策略说明了有关范围，反应性，产物收率，反应时间，再利用和可回收性的重要问题，这将有助于设计用于其他杂环合成的新合成路线。