(5-(2-bromovinyl)-1H-indol-1-yl)(phenyl)methanone | 1393689-99-0

• 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
• 英文名称: (5-(2-bromovinyl)-1H-indol-1-yl)(phenyl)methanone
• 英文别名: (Z)-(5-(2-bromovinyl)-1H-indol-1-yl)(phenyl)methanone；[5-[(Z)-2-bromoethenyl]indol-1-yl]-phenylmethanone
• CAS: 1393689-99-0
• 化学式: C₁₇H₁₂BrNO
• 分子量: 326.192
• InChiKey: SOHVWZKABUQEHJ-NTMALXAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (5-(2-bromovinyl)-1H-indol-1-yl)(phenyl)methanone 在 dipotassium peroxodisulfate 、 copper(l) iodide 、 烟酸乙酯 、 四丁基溴化铵 、 potassium carbonate 、 copper(ll) bromide 、 N,N'-二甲基乙二胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 42.0h， 生成 phenyl(5-(2-(thiophen-3-yl)oxazol-5-yl)-1H-indol-1-yl)-methanone
  参考文献：
  名称：

  Room Temperature Copper(II)-Catalyzed Oxidative Cyclization of Enamides to 2,5-Disubstituted Oxazoles via Vinylic C–H Functionalization

  摘要：

  A copper(11)-catalyzed oxidative cyclization of enamides to oxazoles via vinylic C-H bond functionalization at room temperature is described. Various 2,5-disubstituted oxazoles bearing aryl, vinyl, alkyl, and heteroaryl substituents could be synthesized in moderate to high yields. This reaction protocol is complementary to our previously reported iodine-mediated cyclization of enamides to afford 2,4,5-trisubstituted oxazoles.

  DOI：

  10.1021/jo301332s
• 作为产物：
  描述：

  1-benzoyl-1H-indole-5-carbaldehyde 、 溴甲基三苯基溴化磷 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以63%的产率得到(5-(2-bromovinyl)-1H-indol-1-yl)(phenyl)methanone
  参考文献：
  名称：

  Room Temperature Copper(II)-Catalyzed Oxidative Cyclization of Enamides to 2,5-Disubstituted Oxazoles via Vinylic C–H Functionalization

  摘要：

  A copper(11)-catalyzed oxidative cyclization of enamides to oxazoles via vinylic C-H bond functionalization at room temperature is described. Various 2,5-disubstituted oxazoles bearing aryl, vinyl, alkyl, and heteroaryl substituents could be synthesized in moderate to high yields. This reaction protocol is complementary to our previously reported iodine-mediated cyclization of enamides to afford 2,4,5-trisubstituted oxazoles.

  DOI：

  10.1021/jo301332s

文献信息

• Mild and General Conditions for Negishi Cross-Coupling Enabled by the Use of Palladacycle Precatalysts
  作者：Yang Yang、Nathan J. Oldenhuis、Stephen L. Buchwald

  DOI：10.1002/anie.201207750

  日期：2013.1.7

  A wide range of biaryls were synthesized by palladium‐catalyzed Negishi cross‐couplings at ambient temperature or with low catalyst loading. This protocol features the use of a recently reported aminobiphenyl palladacycle precatalyst to generate the catalytically active XPhosPd0 species. Significantly, a wide range of challenging heterocyclic and polyfluorinated aromatic substrates can be employed

  在环境温度或低催化剂负载量下，通过钯催化的根岸交叉偶联合成了多种联芳基化合物。该协议的特点是使用最近报道的氨基联苯钯环预催化剂来生成具有催化活性的 XPhosPd 0物质。值得注意的是，可以采用各种具有挑战性的杂环和多氟化芳香族底物来获得高产率的产品。
• Room Temperature Copper(II)-Catalyzed Oxidative Cyclization of Enamides to 2,5-Disubstituted Oxazoles via Vinylic C–H Functionalization
  作者：Chi Wai Cheung、Stephen L. Buchwald

  DOI：10.1021/jo301332s

  日期：2012.9.7

  A copper(11)-catalyzed oxidative cyclization of enamides to oxazoles via vinylic C-H bond functionalization at room temperature is described. Various 2,5-disubstituted oxazoles bearing aryl, vinyl, alkyl, and heteroaryl substituents could be synthesized in moderate to high yields. This reaction protocol is complementary to our previously reported iodine-mediated cyclization of enamides to afford 2,4,5-trisubstituted oxazoles.