1-叔丁氧羰基-6-(4-甲氧基苯基)吲哚 | 147621-14-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 中文名称: 1-叔丁氧羰基-6-(4-甲氧基苯基)吲哚
• 英文名称: 1-tert-butoxycarbonyl-6-(4-methoxyphenyl)indole
• 英文别名: 6-(4-methoxyphenyl)-1-tert-butoxycarbonylindole；tert-butyl 6-(4-methoxyphenyl)indole-1-carboxylate
• CAS: 147621-14-5
• 化学式: C₂₀H₂₁NO₃
• 分子量: 323.392
• InChiKey: MDLWBFDCHOGELO-UHFFFAOYSA-N

物化性质

• 沸点：
  470.5±47.0 °C(predicted)
• 密度：
  1.10±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  40.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-叔丁氧羰基-6-(4-甲氧基苯基)吲哚 、 sodium hydroxide 、 二氯甲烷 、 水 在 Brine 、 silica gel 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 2.5h， 以Flash chromatography on silica gel (100 g, 25% ethyl acetate, hexanes) afforded 6-(4-methoxyphenyl)indole as white flakes (2.2 g, 81%)的产率得到6-(4-methoxyphenyl)-1H-indole
  参考文献：
  名称：

  Platelet activating factor antagonists

  摘要：

  在3位取代的吲哚化合物中，通过7-羰基(pyridin-3-基)吡咯[1,2-c]噻唑，7-羰基(pyridin-3-基)吡咯[1,2-c]噁唑或7-羰基(pyridin-3-基)吡咯[1,2-c]吡咯基团的化合物是PAF的有效拮抗剂，并可用于治疗与PAF相关的疾病，包括哮喘、休克、呼吸窘迫综合征、急性炎症、移植器官排斥、胃肠溃疡、过敏性皮肤病、迟缓的细胞免疫、分娩、胎儿肺成熟和细胞分化。

  公开号：

  US05459152A1
• 作为产物：
  描述：

  6-溴吲哚 在 4-二甲氨基吡啶 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium phosphate 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 51.0h， 生成 1-叔丁氧羰基-6-(4-甲氧基苯基)吲哚
  参考文献：
  名称：

  Arylboronic Acids and Arylpinacolboronate Esters in Suzuki Coupling Reactions Involving Indoles. Partner Role Swapping and Heterocycle Protection

  摘要：

  Yields of Suzuki couplings involving indoles depended upon (i) whether arylboronic acids or arylpinacolboronate esters were used, (ii) whether the heterocycle was the aryl halide or the arylboron coupling partner, and (iii) whether the heterocycle was protected or not. Highest yields, which were unaffected by incorporating Boc or Tos protection at the heterocyclic nitrogen, were obtained when indole bromides were reacted with phenylboronic acids. When indolylboronic acids were reacted with phenyl bromides, yields were somewhat lower and depended on the nitrogen substituent, being highest in the absence of protection, lower in the presence of the Boc group, and lowest of all with the Tos group. Arylpinacolboronate esters were less reactive than arylboronic acids. They required considerably longer reaction times and furnished generally lower yields of biaryl. Furthermore, irrespective of whether the heterocycle was the aryl bromide or the arylpinacolboronate ester, these yields were highest when it was protected with the Tos group. Yields were lower with the Boc group, and unprotected heterocycles gave only traces of biaryl. Careful selection of arylboron reagent, of coupling partner roles, and of protecting groups are essential to ensuring optimum results in these Suzuki couplings. These results may also be relevant to couplings involving other substrates.

  DOI：

  10.1021/jo0491612

文献信息

• PLATELET ACTIVATING FACTOR ANTAGONISTS
  申请人：ABBOTT LABORATORIES

  公开号：EP0595924B1

  公开（公告）日：1999-04-14
• US5459152A
  申请人：——

  公开号：US5459152A

  公开（公告）日：1995-10-17