5,9-Dihydro-furo[3',4';6,7]cyclohepta[2,1-b;5,4,3-c',d']diindole-1,3-dione | 188185-76-4

• 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: 5,9-Dihydro-furo[3',4';6,7]cyclohepta[2,1-b;5,4,3-c',d']diindole-1,3-dione
• 英文别名: 13-oxa-3,18-diazahexacyclo[14.6.1.02,10.04,9.011,15.019,23]tricosa-1(23),2(10),4,6,8,11(15),16,19,21-nonaene-12,14-dione
• CAS: 188185-76-4
• 化学式: C₂₀H₁₀N₂O₃
• 分子量: 326.311
• InChiKey: MITAOCVGTVBCFL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.62
• 重原子数：
  25.0
• 可旋转键数：
  0.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.95
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5,9-Dihydro-furo[3',4';6,7]cyclohepta[2,1-b;5,4,3-c',d']diindole-1,3-dione 在 六甲基二硅氮烷 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以67%的产率得到Arcyriacyanin
  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：

  N-Methylarcyriacyanin 在 氢氧化钾 作用下， 反应 0.33h， 以78%的产率得到5,9-Dihydro-furo[3',4';6,7]cyclohepta[2,1-b;5,4,3-c',d']diindole-1,3-dione
  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.