1,3,3-trimethyl-2-(2-phenylethynyl)-3H-indolium triflate

• 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: 1,3,3-trimethyl-2-(2-phenylethynyl)-3H-indolium triflate
• 英文别名: Trifluoromethanesulfonate;1,3,3-trimethyl-2-(2-phenylethynyl)indol-1-ium
• 化学式: CF₃O₃S*C₁₉H₁₈N
• 分子量: 409.429
• InChiKey: HKJFTJOPASWSJZ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  68.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,3,3-trimethyl-2-(2-phenylethynyl)-3H-indolium triflate 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 12.0h， 生成 (2,3-dihydro-7-phenyl-5H-cyclopenta-1,4-dioxin)-5-spiro-2'-(2',3'-dihydro-1,3,3-trimethyl-1H-indole)
  参考文献：
  名称：

  5-Aminocyclopentadienes by intramolecular addition of enolether to aminoallene functionalities

  摘要：

  3-(1-Alkoxyvinyl)-1-aminoallenes 6 were generated by conjugate addition of acyclic and cyclic (1-alkoxyvinyl)cuprates with the semicyclic propyne iminium salt 4. They isomerized smoothly into spiroannellated cyclopentadienes 7 through a 1,5-cyclization that in some cases occurred already at less than or equal to20degreesC. (1-Methoxyallenyl)cuprates reacted with salt 4 in a 2:1 ratio to give the 5,5-dimethoxy-4-methylenepentalene-1-spiro-2'-dihydroindole derivative 10. The thermal isomerization of morpholinoallene 12 into cyclopentadiene 13 indicates that the novel 1,5-cyclization can be extended to other 3-(1-alkoxyvinyl)-1-aminoallenes as well. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01427-8
• 作为产物：
  描述：

  1,3,3-trimethyl-2-phenacylidenindoline 以 二氯甲烷 为溶剂， 反应 0.33h， 生成 1,3,3-trimethyl-2-(2-phenylethynyl)-3H-indolium triflate
  参考文献：
  名称：

  Reinhard, Robert; Maas, Gerhard; Bohrisch, Joerg, Liebigs Annalen der Chemie, 1994, # 4, p. 429 - 432

  摘要：

  DOI：

文献信息

• Tri- and Tetracyclic Azepine Derivatives by Thermally Induced Cyclization of Aminoallenes and Semicyclic 2-Dienamines
  作者：Robert Reinhard、Martina Glaser、Ralf Neumann、Gerhard Maas

  DOI：10.1021/jo9710036

  日期：1997.10.1

  The 3,3-dimethylindoline-derived allenes 5 are conveniently prepared by organocuprate addition to 2-(phenylethynyl)-3,3-dimethyl-1-methylindolium triflate 4. Their thermal isomerization affords tetracyclic azepine derivatives 6. The semicyclic 2-amino 1,3-dienes 11, formed by spontaneous tautomerization of the corresponding aminoallenes, are transformed by thermal reaction into either tricyclic azepine derivatives 13 or benzothiophene-annelated azaheterocycles 14 and 15, depending on the ring size of the enamine moiety and the (hetero)aryl group at C-4 of the 2-dienamine.
• Reinhard, Robert; Maas, Gerhard; Bohrisch, Joerg, Liebigs Annalen der Chemie, 1994, # 4, p. 429 - 432
  作者：Reinhard, Robert、Maas, Gerhard、Bohrisch, Joerg、Liebscher, Juergen

  DOI：——

  日期：——
• 5-Aminocyclopentadienes by intramolecular addition of enolether to aminoallene functionalities
  作者：Robert Reinhard、Jens Schlegel、Gerhard Maas

  DOI：10.1016/s0040-4020(02)01427-8

  日期：2002.12

  3-(1-Alkoxyvinyl)-1-aminoallenes 6 were generated by conjugate addition of acyclic and cyclic (1-alkoxyvinyl)cuprates with the semicyclic propyne iminium salt 4. They isomerized smoothly into spiroannellated cyclopentadienes 7 through a 1,5-cyclization that in some cases occurred already at less than or equal to20degreesC. (1-Methoxyallenyl)cuprates reacted with salt 4 in a 2:1 ratio to give the 5,5-dimethoxy-4-methylenepentalene-1-spiro-2'-dihydroindole derivative 10. The thermal isomerization of morpholinoallene 12 into cyclopentadiene 13 indicates that the novel 1,5-cyclization can be extended to other 3-(1-alkoxyvinyl)-1-aminoallenes as well. (C) 2002 Elsevier Science Ltd. All rights reserved.