tert-butyl 2-iodo-5-(trifluoromethyl)phenylcarbamate | 1448535-57-6

• 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 2-iodo-5-(trifluoromethyl)phenylcarbamate
• 英文别名: t-butyl (2-iodo-5-(trifluoromethyl)phenyl)carbamate；tert-Butyl (2-iodo-5-(trifluoromethyl)phenyl)carbamate；tert-butyl N-[2-iodo-5-(trifluoromethyl)phenyl]carbamate
• CAS: 1448535-57-6
• 化学式: C₁₂H₁₃F₃INO₂
• 分子量: 387.14
• InChiKey: PVGSKBYUPGYKOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-iodo-5-(trifluoromethyl)phenylcarbamate 在 三氟化硼乙醚 、 四乙基氯化铵 、 potassium acetate 、 palladium diacetate 、 二异丁基氢化铝 、 N,N-二异丙基乙胺 、 三苯基膦 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 9.01h， 生成 tert-butyl 3-methyl-6-(trifluoromethyl)-1H-indole-1-carboxylate
  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
• 作为产物：
  描述：

  3-氨基-4-碘三氟甲苯 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 2-iodo-5-(trifluoromethyl)phenylcarbamate
  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

• Carbolithiation of Chloro-Substituted Alkynes: A New Access to Vinyl Carbenoids
  作者：Rudy Lhermet、Maha Ahmad、Catherine Fressigné、Bernard Silvi、Muriel Durandetti、Jacques Maddaluno

  DOI：10.1002/chem.201403605

  日期：2014.8.11

  The intramolecular carbolithiation of a series of chloro‐substituted alkynes leads to exocyclic alkylidene carbenoids of which both nucleophilic and electrophilic characters can be drove. A sole stereoselective 5‐exo‐dig addition takes place, probably because of a strong and persisting Li–Cl interaction arising before the transition state.

  一系列氯取代炔烃的分子内碳烷化作用会导致环外亚烷基类胡萝卜素，其亲核和亲电特性均可被驱动。发生唯一的立体选择性5 exo-dig加成反应，可能是由于在过渡态之前发生了强烈且持久的Li-Cl相互作用。