3-cyclohexylidene-2-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]acrylic acid methyl ester | 952527-38-7

• 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: 3-cyclohexylidene-2-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]acrylic acid methyl ester
• CAS: 952527-38-7
• 化学式: C₂₅H₂₅NO₄S
• 分子量: 435.544
• InChiKey: SIYTVAUEJMIFCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.23
• 重原子数：
  31.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  65.37
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-cyclohexylidene-2-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]acrylic acid methyl ester 在 氨 、 zinc trifluoromethanesulfonate 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 30.0h， 生成 3-cyclohex-1-enyl-4-(1-tosyl-1H-indol-3-yl)-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  Efficient Synthesis of Maleimides and Carbazoles via Zn(OTf)₂-Catalyzed Tandem Annulations of Isonitriles and Allenic Esters

  摘要：

  Lewis acid Zn(OTf)(2)-catalyzed tandem annulations of isonitriles and allenic esters which lead to efficient and flexible syntheses of a range of biologically significant maleimides and carbazoles and related compounds are reported. A mechanistic rationale is proposed to account for the observed reactivity.

  DOI：

  10.1021/ol7018086
• 作为产物：
  描述：

  1-tosyl-3-((trimethylsilyl)ethynyl)-1H-indole 在 四(三苯基膦)钯 正丁基锂 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 正己烷 、 苯 为溶剂， 反应 28.25h， 生成 3-cyclohexylidene-2-[1-(toluene-4-sulfonyl)-1H-indol-3-yl]acrylic acid methyl ester
  参考文献：
  名称：

  Efficient Synthesis of Maleimides and Carbazoles via Zn(OTf)₂-Catalyzed Tandem Annulations of Isonitriles and Allenic Esters

  摘要：

  Lewis acid Zn(OTf)(2)-catalyzed tandem annulations of isonitriles and allenic esters which lead to efficient and flexible syntheses of a range of biologically significant maleimides and carbazoles and related compounds are reported. A mechanistic rationale is proposed to account for the observed reactivity.

  DOI：

  10.1021/ol7018086

文献信息

• Electronic Effect Directed Au(I)-Catalyzed Cyclic C2–H Bond Functionalization of 3-Allenylindoles
  作者：Bo Chen、Wu Fan、Guobi Chai、Shengming Ma

  DOI：10.1021/ol301408g

  日期：2012.7.20

  Gold-catalyzed cyclization reactions of indoles with an electron-deficient allene at the 3-position led to formation of dihydrocyclopenta[b]indole derivatives in moderate to excellent yields via C2-H bond functionalization of the indole unit. The presence of the electron-withdrawing alkoxycarbonyl, dialkoxyphosphono, or phenyl is crutial for this transformation. The potential synthetic dihydrocyclopenta[b]indole with the electron-withdrawing group has been demonstrated by applying a [3 + 2] cycloaddition reaction to construct the tretracycloskeleton.