tert-butyl (5-chloro-2-iodophenyl)carbamate | 153042-33-2

• 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: tert-butyl (5-chloro-2-iodophenyl)carbamate
• 英文别名: Tert-butyl 5-chloro-2-iodophenylcarbamate；tert-butyl N-(5-chloro-2-iodophenyl)carbamate
• CAS: 153042-33-2
• 化学式: C₁₁H₁₃ClINO₂
• 分子量: 353.587
• InChiKey: SMWZWURJQZQFEO-UHFFFAOYSA-N

物化性质

• 沸点：
  318.8±32.0 °C(Predicted)
• 密度：
  1.664±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 储存条件：
  存储温度应保持在2-8°C，并请避免光照。

反应信息

• 作为反应物：
  描述：

  tert-butyl (5-chloro-2-iodophenyl)carbamate 以66的产率得到tert-butyl N-(5-chloro-2-trimethylstannylphenyl)carbamate
  参考文献：
  名称：

  J. Med. Chem. 1994, 37, 334-336

  摘要：

  DOI：
• 作为产物：
  描述：

  5-氯-2-碘苯胺 在 甲醇 、 4-二甲氨基吡啶 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 tert-butyl (5-chloro-2-iodophenyl)carbamate
  参考文献：
  名称：

  Microwave-assisted synthesis of 3-substituted indoles via intramolecular arene–alkene coupling of o-iodoanilino enamines

  摘要：

  A generally applicable and high-yielding protocol for the synthesis of 3-substituted indole derivatives is described. Key features include microwave-assisted intramolecular arene alkene coupling of o-iodoanilino enamines, and expedient synthesis of o-iodoanilino enamine substrates employing N,O-acetal TMS ethers, which could be conveniently derived from the corresponding amides. Our unique procedure seems quite efficient and provides an easy access to a variety of 3-substituted indoles as privileged structure for a wide range of biological targets. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.06.101

文献信息

• [EN] INHIBITORS OF CYTOMEGALOVIRUS<br/>[FR] INHIBITEURS DE CYTOMÉGALOVIRUS
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2014070976A1

  公开（公告）日：2014-05-08

  Compounds of Formula (I) wherein R1, R2, R3A, R3B, Y, Z1 and Z2 are defined herein, are useful for the treatment of cytomegalovirus disease and/or infection.

  式（I）中R1、R2、R3A、R3B、Y、Z1和Z2所定义的化合物对巨细胞病毒疾病和/或感染的治疗具有用处。
• Convenient synthesis of 2-substituted indoles from 2-ethynylanilines with tetrabutylammonium fluoride
  作者：Akito Yasuhara、Yuichi Kanamori、Masashi Kaneko、Atsushi Numata、Yoshinori Kondo、Takao Sakamoto

  DOI：10.1039/a808842j

  日期：——

  The cyclization reaction of various 2-ethynylanilines, which were easily synthesized from 2-haloanilines by the palladium-catalyzed reaction with terminal alkynes, with tetrabutylammonium fluoride (TBAF) to yield 2-substituted indoles proceeded at refluxing or room temperature in THF in excellent yields without affecting the bromo, chloro, cyano, ethoxycarbonyl, and ethynyl groups.

  通过钯催化的末端炔烃与2-卤代苯胺的反应，易于合成的各种2-乙炔基苯胺，在四丁基氟化铵（TBAF）的作用下，以优异的产率在回流或室温下的四氢呋喃中进行环化反应，生成2-取代的吲哚，且不影响溴、氯、氰基、乙氧羰基和乙炔基团。
• Highly Enantioselective Cross-Electrophile Aryl-Alkenylation of Unactivated Alkenes
  作者：Zhi-Xiong Tian、Jin-Bao Qiao、Guang-Li Xu、Xiaobo Pang、Liangliang Qi、Wei-Yuan Ma、Zhen-Zhen Zhao、Jicheng Duan、Yun-Fei Du、Peifeng Su、Xue-Yuan Liu、Xing-Zhong Shu

  DOI：10.1021/jacs.9b03863

  日期：2019.5.8

  respect to data, studies have mainly focused on stereoconvergent reactions of racemic alkyl electrophiles. Here, we report an enantioselective cross-electrophile aryl-alkenylation reaction of unactivated alkenes. This method provides access to a number of biologically important chiral molecules such as dihydrobenzofurans, indolines, and indanes. The incorporated alkenyl group is suitable for further

  对映选择性交叉亲电试剂反应仍然是金属催化中的一个具有挑战性的课题，在数据方面，研究主要集中在外消旋烷基亲电试剂的立体会聚反应上。在这里，我们报告了未活化烯烃的对映选择性交叉亲电子芳基-烯基化反应。该方法提供了获得许多生物学上重要的手性分子的途径，例如二氢苯并呋喃、二氢吲哚和茚满。引入的烯基适用于可导致分子多样性和复杂性增加的进一步反应。该反应在室温下温和条件下进行，并且易于获得的手性辉石配体用于提供具有高对映选择性的产物。
• Diversely Substituted Quinolines via Rhodium-Catalyzed Alkyne Hydroacylation
  作者：James D. Neuhaus、Sarah M. Morrow、Michael Brunavs、Michael C. Willis

  DOI：10.1021/acs.orglett.6b00390

  日期：2016.4.1

  hydroacylative union of aldehydes and o-alkynyl anilines leads to 2-aminophenyl enones, and onward to substituted quinolines. The mild reaction conditions employed in this chemistry result in a process that displays broad functional group tolerance, allowing the preparation of diversely substituted quinolines in high yields. Extension to the use of o-alkynyl nitro arenes as substrates leads to 2-nitrochalcones

  醛和邻炔基苯胺的Rh催化的氢酰基联合产生2-氨基苯基烯酮，并进一步生成取代的喹啉。在该化学反应中使用的温和反应条件导致显示出宽泛的官能团耐受性的过程，从而可以高收率制备各种取代的喹啉。扩展使用邻炔基硝基芳烃作为底物会产生2-硝基查耳酮，从中可以得到喹啉和喹啉N-氧化物。
• A new synthetic approach to pyrrolo[3,2- b ]indoles via regioselective formation of pyrrole and intramolecular C N coupling
  作者：Manjusha V. Karkhelikar、Vijay V. Rao、Sundar S. Shinde、Pravin R. Likhar

  DOI：10.1016/j.tetlet.2016.09.044

  日期：2016.10

  A new synthetic approach for the synthesis of pyrrolo[3,2-b]indoles has been developed in two steps. First step involves electrophilic iodocyclization of protected 2-alkynylanilines to regioselective formation of pyrroles followed by copper catalyzed intramolecular CN coupling.

  分两个步骤开发了一种合成吡咯并[3,2- b ]吲哚的新合成方法。第一步涉及被保护的2-炔基苯胺的亲电碘环化，以形成吡咯的区域选择性，然后进行铜催化的分子内C N偶联。