4-(4-methoxyphenyl)-2-phenyl-1-tosyl-1H-indole | 1599442-34-8

• 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: 4-(4-methoxyphenyl)-2-phenyl-1-tosyl-1H-indole
• 英文别名: 4-(4-Methoxyphenyl)-1-(4-methylphenyl)sulfonyl-2-phenylindole；4-(4-methoxyphenyl)-1-(4-methylphenyl)sulfonyl-2-phenylindole
• CAS: 1599442-34-8
• 化学式: C₂₈H₂₃NO₃S
• 分子量: 453.562
• InChiKey: KAYZBEDJRBPSMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  56.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,3-二氯苯胺 在 吡啶 、 双(乙腈)氯化钯(II) 、 potassium phosphate 、 Cy-DHTP*HBF₄ 、 lithium tert-butoxide 作用下， 以 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 12.67h， 生成 4-(4-methoxyphenyl)-2-phenyl-1-tosyl-1H-indole
  参考文献：
  名称：

  One-Pot Synthesis of 2,4-Disubstituted Indoles fromN-Tosyl-2,3-dichloroaniline Using Palladium–Dihydroxyterphenylphosphine Catalyst

  摘要：

  4-Chloroindoles were synthesized from readily available 2,3-dichloroaniline derivatives and terminal alkynes. The catalyst composed of palladium and dicyclohexyl(dihydroxyterphenyl)phosphine (Cy-DHTP) enabled ortho-selective Sonogashira coupling, and subsequent cyclization afforded 4-chloroindoles in high yields. This transformation was successfully applied to the one-pot synthesis of 2,4-disubstituted indoles via Suzuki-Miyaura coupling after indole formation.

  DOI：

  10.1021/ol500711z

文献信息

• One-Pot Synthesis of Substituted Benzo[<i>b</i>]furans and Indoles from Dichlorophenols/Dichloroanilines Using a Palladium–Dihydroxyterphenylphosphine Catalyst
  作者：Miyuki Yamaguchi、Tomoyo Akiyama、Hirohisa Sasou、Haruka Katsumata、Kei Manabe

  DOI：10.1021/acs.joc.6b00824

  日期：2016.7.1

  Sonogashira coupling of dichlorophenols and terminal alkynes, followed by cyclization and Suzuki–Miyaura coupling in one pot, using a palladium–dihydroxyterphenylphosphine (Cy-DHTP) catalyst. The use of substoichiometric amounts of tetrabutylammonium chloride was effective in accelerating the Suzuki–Miyaura coupling. This protocol was also successfully applied to the one-pot synthesis of disubstituted

  二取代的苯并[ b ]呋喃是通过二氯苯酚和末端炔的邻位选择性Sonogashira偶联反应，然后使用钯-二羟基叔苯基膦（Cy-DHTP）催化剂在一个罐中进行环化和Suzuki-Miyaura偶联反应而合成的。亚化学计量的四丁基氯化铵的使用有效地加速了Suzuki-Miyaura偶联。该方案也成功地用于从二氯苯胺衍生物的一锅法合成二取代的吲哚。
• One-Pot Synthesis of 2,4-Disubstituted Indoles from<i>N</i>-Tosyl-2,3-dichloroaniline Using Palladium–Dihydroxyterphenylphosphine Catalyst
  作者：Miyuki Yamaguchi、Kei Manabe

  DOI：10.1021/ol500711z

  日期：2014.5.2

  4-Chloroindoles were synthesized from readily available 2,3-dichloroaniline derivatives and terminal alkynes. The catalyst composed of palladium and dicyclohexyl(dihydroxyterphenyl)phosphine (Cy-DHTP) enabled ortho-selective Sonogashira coupling, and subsequent cyclization afforded 4-chloroindoles in high yields. This transformation was successfully applied to the one-pot synthesis of 2,4-disubstituted indoles via Suzuki-Miyaura coupling after indole formation.