N-Methylarcyriacyanin | 188185-69-5

• 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: N-Methylarcyriacyanin
• 英文别名: 13-methyl-3,13,18-triazahexacyclo[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: 188185-69-5
• 化学式: C₂₁H₁₃N₃O₂
• 分子量: 339.353
• InChiKey: ZCLTZFYDOLQCAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.54
• 重原子数：
  26.0
• 可旋转键数：
  0.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  68.96
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  N-Methylarcyriacyanin 在 氢氧化钾 、 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 12.33h， 生成 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：

  (2-(2-methyl-3-nitrophenoxy)tetrahydro-2H-pyran) 在 palladium diacetate 、 palladium on activated charcoal 四氢吡咯 、 4-二甲氨基吡啶 、 Amberlite 、 1,3-双(二苯基膦)丙烷 、 乙基溴化镁 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 51.0h， 生成 N-Methylarcyriacyanin
  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

• Unexpected Formation of the Arcyriacyanin System by Condensation of a 3-Bromo-4-(indol-3-yl)maleimide with (2-Nitrophenyl)acetates
  作者：Guido Mayer、Claudia Hinze、Kurt Polborn、Wolfgang Steglich

  DOI：10.1071/ch04043

  日期：——

  The reaction of an N-protected 3-bromo-4-(indol-3-yl)maleimide with methyl (2-nitrophenyl)acetates in the presence of base affords condensed cycloheptatriene derivatives which can be transformed into arcyriacyanin-type alkaloids. The unusual reaction sequence implies a heptatrienyl–cycloheptadienyl anion rearrangement followed by a 1,5-sigmatropic shift to yield the thermodynamically more stable cycloheptatriene derivative.

  在碱存在下，N-保护的 3-溴-4-(吲哚-3-基)马来酰亚胺与(2-硝基苯基)乙酸甲酯反应生成缩合环庚三烯衍生物，这些衍生物可转化为arcyriacyanin类生物碱。不寻常的反应顺序意味着庚三烯-环庚二烯阴离子重排，然后发生 1,5-sigmatropic 转变，生成热力学上更稳定的环庚三烯衍生物。
• 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.