11b-(trifluoromethyl)-5,6,11,11b-tetrahydro-1H-indolizino[8,7-b]indol-3(2H)-one | 187928-15-0

• 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: 11b-(trifluoromethyl)-5,6,11,11b-tetrahydro-1H-indolizino[8,7-b]indol-3(2H)-one
• 英文别名: 1,5,6,9b-tetrahydro-9b-trifluoromethylindolizino[8,7-b]indol-3(2H)-one；11b-(trifluoromethyl)-2,5,6,11-tetrahydro-1H-indolizino[8,7-b]indol-3-one
• CAS: 187928-15-0
• 化学式: C₁₅H₁₃F₃N₂O
• 分子量: 294.276
• InChiKey: PSCIYMWAXQULBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  36.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  11b-(trifluoromethyl)-5,6,11,11b-tetrahydro-1H-indolizino[8,7-b]indol-3(2H)-one 在 三氟化硼四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 以98%的产率得到11b-(trifluoromethyl)-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole
  参考文献：
  名称：

  Synthesis of Indolizidine Derivatives Trifluoromethylated at Bridgehead Position via Acyl Iminium Ion Intermediates Derived from Ring-Chain Tautomerism of 5,5,5-Trifluoro-4-oxopentanoyl Arylethylamides

  摘要：

  DOI：

  10.3987/com-96-s12
• 作为产物：
  描述：

  5-hydroxy-1-[2-(1H-indol-3-yl)ethyl]-5-(trifluoromethyl)pyrrolidin-2-one 在 甲烷磺酸 作用下， 以 1,2-二氯乙烷 为溶剂， 以38 mg的产率得到11b-(trifluoromethyl)-5,6,11,11b-tetrahydro-1H-indolizino[8,7-b]indol-3(2H)-one
  参考文献：
  名称：

  One-Pot Cascade Trifluoromethylation/Cyclization of Imides: Synthesis of α-Trifluoromethylated Amine Derivatives

  摘要：

  Tryptamine- and phenethylamine-derived imides were selectively monotrifluoromethylated using CF3TMS. Subsequent methanesulfonic acid mediated cyclization of the intermediate hemiaminals afforded the alpha-trifluoromethylated amine derivatives via the formation of trifluoromethylated acyliminium ions, in one pot. The strategy was applicable to the both inter- and intramolecular versions. Furthermore, the utility of the present method was demonstrated through the synthesis of trifluoromethylated analogues of harmicine and crispine A.

  DOI：

  10.1021/jo5002998

文献信息

• Diverse synthesis of natural product inspired fused and spiro-heterocyclic scaffolds via ring distortion and ring construction strategies
  作者：Chandramohan Bathula、Poonam Dangi、Santanu Hati、Rahul Agarwal、Parthapratim Munshi、Ashutosh Singh、Shailja Singh、Subhabrata Sen

  DOI：10.1039/c5nj01858g

  日期：——

  A toolkit of indole scaffolds inspired from natural products.

  一种受自然产物启发的吲哚骨架工具包。