(2-bromo-4,6-difluorophenyl)-carbamic acid tert-butyl ester | 384793-23-1

• 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-bromo-4,6-difluorophenyl)-carbamic acid tert-butyl ester
• 英文别名: N-(tert-Butoxycarbonyl)-2-bromo-4,6-difluoroaniline；tert-butyl N-(2-bromo-4,6-difluorophenyl)carbamate
• CAS: 384793-23-1
• 化学式: C₁₁H₁₂BrF₂NO₂
• 分子量: 308.123
• InChiKey: RXMHLCZOGUHSIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 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：
  4

反应信息

• 作为反应物：
  描述：

  (2-bromo-4,6-difluorophenyl)-carbamic acid tert-butyl ester 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 sodium ethanolate 、 三乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 5,7-二氟吲哚
  参考文献：
  名称：

  [EN] INDOLE AHR INHIBITORS AND USES THEREOF
  [FR] INHIBITEURS D'INDOLE AHR ET LEURS UTILISATIONS

  摘要：

  公开号：

  WO2018195397A3
• 作为产物：
  描述：

  2-溴-4,6-二氟苯胺 在 4-二甲氨基吡啶 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 42.0h， 生成 (2-bromo-4,6-difluorophenyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Indole Synthesis by Controlled Carbolithiation of o-Aminostyrenes

  摘要：

  An effective synthesis of the functionalized indole ring system has been developed from substituted o-aminostyrene starting material. Our methodology involves a novel cascade reaction sequence of alkyllithium addition to the styrene double bond and subsequent trapping of the intermediate organolithium with a suitable electrophile, followed by an in situ ring closure and dehydration to generate the indole ring. This new reaction sequence allows for the introduction of molecular diversity at all positions on the indole scaffold. The procedure was shown to be successful with a range of both C and N substituents on the o-aminostyrenes. The reaction sequence was tolerant to the reactivity range of alkyllithiums such as tert-, sec-, and n-butyllithium. The electrophiles used were DMF, which generated indole products with C-2 unsubstituted, and nitriles, which incorporated the nitrile substituent at C-2. The o-aminostyrene starting materials were generated by a Pd-catalyzed cross-coupling reaction of a vinyl boronic acid equivalent with the readily available substituted o-bromoanilines.

  DOI：

  10.1021/jo048723e

文献信息

• A Sequential Transition Metal and Organocatalytic Approach to the Enantioselective Synthesis of C2-Spiroindoline Systems
  作者：Pooja Sah、Aakash Kumar Gond、Gaurav Saini、Manmohan Kapur

  DOI：10.1021/acs.orglett.3c03716

  日期：2023.12.29

  We report herein an organocatalyzed enantioselective spirocyclization strategy to access valuable C2-spiroindoline scaffolds bearing a quaternary stereocenter via an aza-Michael addition reaction, wherein the acid additive plays the role of dual functionality. The substrates for this key step were put together by an exo-selective, Pd-catalyzed γ-arylation of silyldienol ethers of the corresponding

  我们在此报道了一种有机催化的对映选择性螺环化策略，通过氮杂-迈克尔加成反应获得有价值的带有四元立构中心的C2-螺吲哚啉支架，其中酸添加剂起到双重功能的作用。该关键步骤的底物是通过相应环己烯酮的甲硅烷基二烯醇醚的外选择性、Pd 催化的 γ-芳基化而组合在一起的。低催化剂负载量和慢反应速率之间的紧密结合产生了具有良好对映选择性的C2-螺吲哚啉。
• [EN] SUBSTITUTED HYDROXYETHYLAMINE ASPARTYL PROTEASE INHIBITORS<br/>[FR] ASPARTYLE A BASE D'HYDROXYETHYLAMINE INHIBITEURS DE LA PROTEASE
  申请人：ELAN PHARM INC

  公开号：WO2005087752A3

  公开（公告）日：2006-04-13
• AN IMPROVED SYNTHESIS OF<i>N</i>-BOC PROTECTED ARYL AMINES
  作者：Shelley Darnbrough、Miljenko Mervic、Stephen M. Condon、Christopher J. Burns

  DOI：10.1081/scc-100106036

  日期：2001.1

  There are several known methods of protecting amines as their Boc derivatives. For less nucleophilic amines such as aryl amines these methods often give poor yields and are generally not satisfactory. Here, Boc aryl amines are obtained by first introducing two Boc groups followed by selective removal of one of them. This procedure works well for a number highly sterically hindered substrates as well as electron deficient and electron rich aryl amines.
• INDOLE AHR INHIBITORS AND USES THEREOF
  申请人：Kyn Therapeutics

  公开号：EP3612030A2

  公开（公告）日：2020-02-26
• Indole Synthesis by Controlled Carbolithiation of <i>o</i>-Aminostyrenes
  作者：Albane Kessler、Claire M. Coleman、Patchanee Charoenying、Donal F. O'Shea

  DOI：10.1021/jo048723e

  日期：2004.11.1

  An effective synthesis of the functionalized indole ring system has been developed from substituted o-aminostyrene starting material. Our methodology involves a novel cascade reaction sequence of alkyllithium addition to the styrene double bond and subsequent trapping of the intermediate organolithium with a suitable electrophile, followed by an in situ ring closure and dehydration to generate the indole ring. This new reaction sequence allows for the introduction of molecular diversity at all positions on the indole scaffold. The procedure was shown to be successful with a range of both C and N substituents on the o-aminostyrenes. The reaction sequence was tolerant to the reactivity range of alkyllithiums such as tert-, sec-, and n-butyllithium. The electrophiles used were DMF, which generated indole products with C-2 unsubstituted, and nitriles, which incorporated the nitrile substituent at C-2. The o-aminostyrene starting materials were generated by a Pd-catalyzed cross-coupling reaction of a vinyl boronic acid equivalent with the readily available substituted o-bromoanilines.