(4S,12bS)-12-tosyl-4-(4-(trifluoromethyl)phenyl)-1,3,4,6,7,12b-hexahydroindolo[2,3-a]quinolizin-2(12H)-one | 1421697-05-3

• 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: (4S,12bS)-12-tosyl-4-(4-(trifluoromethyl)phenyl)-1,3,4,6,7,12b-hexahydroindolo[2,3-a]quinolizin-2(12H)-one
• 英文别名: (4S,12bS)-12-(4-methylphenyl)sulfonyl-4-[4-(trifluoromethyl)phenyl]-1,3,4,6,7,12b-hexahydroindolo[2,3-a]quinolizin-2-one
• CAS: 1421697-05-3
• 化学式: C₂₉H₂₅F₃N₂O₃S
• 分子量: 538.59
• InChiKey: KSTIGVSMPSDWPJ-SVBPBHIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  38
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  67.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  N-[2-(1H-吲哚-3-基)乙基]甲酰胺 在 （2S）-2-[[[[[[（（1R，2R）-2-氨基环己基]氨基]硫代甲基]氨基]-N-（二苯甲基）-N，3,3-三甲基丁酰胺 、 caesium carbonate 、 溶剂黄146 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 、 乙腈 为溶剂， 反应 81.0h， 生成 (4S,12bS)-12-tosyl-4-(4-(trifluoromethyl)phenyl)-1,3,4,6,7,12b-hexahydroindolo[2,3-a]quinolizin-2(12H)-one 、 (4R,12bS)-12-tosyl-4-(4-(trifluoromethyl)phenyl)-1,3,4,6,7,12b-hexahydroindolo[2,3-a]quinolizin-2(12H)-one
  参考文献：
  名称：

  Enantioselective Formal Aza-Diels–Alder Reactions of Enones with Cyclic Imines Catalyzed by Primary Aminothioureas

  摘要：

  A highly enantio- and diastereoselective synthesis of indolo- and benzoquinolizidine compounds has been developed through the formal aza-Diels-Alder reaction of enones with cyclic imines. This transformation is catalyzed by a new bifunctional primary aminothiourea that achieves simultaneous activation of both the enone and imine reaction components.

  DOI：

  10.1021/ja310718f

文献信息

• Oxidative Asymmetric Formal Aza-Diels–Alder Reactions of Tetrahydro-β-carboline with Enones in the Synthesis of Indoloquinolizidine-2-ones
  作者：Xiang Wu、Shi-Bao Zhao、Lang-Lang Zheng、You-Gui Li

  DOI：10.3390/molecules23092228

  日期：——

  Ru-catalyzed tandem amine oxidative dehydrogenation/formal aza-Diels⁻Alder reaction for enantio- and diastereoselective synthesis of indoloquinolizidine-2-ones from tetrahydro-β-carbolines and α,β-unsaturated ketones is described. The reaction proceeds via tandem ruthenium-catalyzed amine dehydrogenation using tert-butyl hydroperoxide (TBHP) as the oxidant and a chiral thiourea-catalyzed formal aza-[4

  描述了Ru催化的串联胺氧化脱氢/形式的氮杂-Diels⁻Alder反应，用于从四氢-β-咔啉和α，β-不饱和酮的对映体和非对映体选择性合成吲哚并喹喔啉-2-酮。该反应通过叔丁基过氧化氢（TBHP）作为氧化剂和手性硫脲催化的正式氮杂-[4 + 2]环加成反应，通过串联钌催化的胺脱氢进行，为合成这些有价值的杂环化合物提供了分步经济的策略产品。
• Enantioselective Formal Aza-Diels–Alder Reactions of Enones with Cyclic Imines Catalyzed by Primary Aminothioureas
  作者：Mathieu P. Lalonde、Meredeth A. McGowan、Naomi S. Rajapaksa、Eric N. Jacobsen

  DOI：10.1021/ja310718f

  日期：2013.2.6

  A highly enantio- and diastereoselective synthesis of indolo- and benzoquinolizidine compounds has been developed through the formal aza-Diels-Alder reaction of enones with cyclic imines. This transformation is catalyzed by a new bifunctional primary aminothiourea that achieves simultaneous activation of both the enone and imine reaction components.