1'-(Toluene-4-sulfonyl)-1'H-[2,4']biindolyl-1-carboxylic acid tert-butyl ester | 188185-73-1

• 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: 1'-(Toluene-4-sulfonyl)-1'H-[2,4']biindolyl-1-carboxylic acid tert-butyl ester
• 英文别名: Tert-butyl 2-[1-(4-methylphenyl)sulfonylindol-4-yl]indole-1-carboxylate
• CAS: 188185-73-1
• 化学式: C₂₈H₂₆N₂O₄S
• 分子量: 486.591
• InChiKey: FNUIFEFYEDNGHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  78.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1'-(Toluene-4-sulfonyl)-1'H-[2,4']biindolyl-1-carboxylic acid tert-butyl ester 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以68%的产率得到2,4'-bi-1H-indole
  参考文献：
  名称：

  Total syntheses of the slime mold alkaloid arcyriacyanin A

  摘要：

  AbstractArcyriacyanin A (1) has been synthesized by three different routes. In the first synthesis the bisbromomagnesium salt of 2,4′‐biindole (5) was treated with dibromomaleimide (6) to yield arcyriacyanin A (1). The second approach used an intramolecular Heck reaction for the cyclization of a 4‐(triflyloxy)arcyriarubin 8 to N‐methylarcyriacyanin A (2). Thirdly, compound 2 was obtained by a domino Heck reaction between 3‐bromo‐4‐[1‐(tert‐butoxycarbonyl)indol‐3‐yl]‐1‐methylmaleimide (9) and 4‐bromoindole (10). The N‐methyl derivative 2 could be transformed into arcyriacyanin A (1) by standard methods.

  DOI：

  10.1002/chem.19970030112
• 作为产物：
  描述：

  4-bromo-1-tosyl-1H-indole 、 1-(tert-butoxycarbonyl)-2-(trimethylstannyl)indole 在 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 反应 20.0h， 以75%的产率得到1'-(Toluene-4-sulfonyl)-1'H-[2,4']biindolyl-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Total syntheses of the slime mold alkaloid arcyriacyanin A

  摘要：

  AbstractArcyriacyanin A (1) has been synthesized by three different routes. In the first synthesis the bisbromomagnesium salt of 2,4′‐biindole (5) was treated with dibromomaleimide (6) to yield arcyriacyanin A (1). The second approach used an intramolecular Heck reaction for the cyclization of a 4‐(triflyloxy)arcyriarubin 8 to N‐methylarcyriacyanin A (2). Thirdly, compound 2 was obtained by a domino Heck reaction between 3‐bromo‐4‐[1‐(tert‐butoxycarbonyl)indol‐3‐yl]‐1‐methylmaleimide (9) and 4‐bromoindole (10). The N‐methyl derivative 2 could be transformed into arcyriacyanin A (1) by standard methods.

  DOI：

  10.1002/chem.19970030112

文献信息

• Total syntheses of the slime mold alkaloid arcyriacyanin A
  作者：Michael Brenner、Guido Mayer、Andreas Terpin、Wolfgang Steglich

  DOI：10.1002/chem.19970030112

  日期：1997.1

  AbstractArcyriacyanin A (1) has been synthesized by three different routes. In the first synthesis the bisbromomagnesium salt of 2,4′‐biindole (5) was treated with dibromomaleimide (6) to yield arcyriacyanin A (1). The second approach used an intramolecular Heck reaction for the cyclization of a 4‐(triflyloxy)arcyriarubin 8 to N‐methylarcyriacyanin A (2). Thirdly, compound 2 was obtained by a domino Heck reaction between 3‐bromo‐4‐[1‐(tert‐butoxycarbonyl)indol‐3‐yl]‐1‐methylmaleimide (9) and 4‐bromoindole (10). The N‐methyl derivative 2 could be transformed into arcyriacyanin A (1) by standard methods.