12b-methyl-2,3,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizin-4-one | 959979-09-0

• 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: 12b-methyl-2,3,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizin-4-one
• 英文别名: (R)-12b-methyl-2,3,6,7,12,12b-hexahydroindolo[2,3-a]quinolizin-4(1H)-one；(12bR)-12b-methyl-1,2,3,6,7,12-hexahydroindolo[2,3-a]quinolizin-4-one
• CAS: 959979-09-0
• 化学式: C₁₆H₁₈N₂O
• 分子量: 254.332
• InChiKey: LWDBHYFCXDXNBF-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  36.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  5-己炔酸 在 R-3,3'-二(三苯基硅基)联萘酚膦酸酯 、 4-二甲氨基吡啶 、 (乙腈)[(2-联苯)二叔丁基膦]六氟锑酸金(I) 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 12.08h， 生成 (S)-12b-methyl-2,3,6,7,12,12b-hexahydroindolo[2,3-a]quinolizin-4(1H)-one 、 12b-methyl-2,3,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizin-4-one
  参考文献：
  名称：

  Gold and BINOL-Phosphoric Acid Catalyzed Enantioselective Hydroamination/N-Sulfonyliminium Cyclization Cascade

  摘要：

  A highly enantioselective hydroamination/N-sulfonyliminium cyclization cascade is reported using a combination of gold(I) and chiral phosphoric acid catalysts. An initial 5-exo-dig hydroamination and a subsequent phosphoric acid catalyzed cyclization process provide access to complex sulfonamide scaffolds in excellent yield and high enantiocontrol. The method can be extended to lactam derivatives, with excellent yields and enantiomeric excesses of up to 93% ee.

  DOI：

  10.1021/ol401784h

文献信息

• Enantioselective Pictet−Spengler-Type Cyclizations of Hydroxylactams:  H-Bond Donor Catalysis by Anion Binding
  作者：Izzat T. Raheem、Parvinder S. Thiara、Emily A. Peterson、Eric N. Jacobsen

  DOI：10.1021/ja076179w

  日期：2007.11.1

  indolizinone and quinolizinone products are obtained in the thiourea-catalyzed cyclization of tryptamine-derived hydroxylactams. Substituent and counterion effect studies point to a novel mechanism of catalysis involving rate-limiting anion abstraction and binding by the thiourea.

  在硫脲催化的色胺衍生的羟基内酰胺的环化中获得高度对映体富集的吲哚嗪酮和喹嗪酮产物。取代基和反离子效应研究指出了一种新的催化机制，涉及限速阴离子提取和硫脲结合。
• Gold and BINOL-Phosphoric Acid Catalyzed Enantioselective Hydroamination/<i>N</i>-Sulfonyliminium Cyclization Cascade
  作者：Alex W. Gregory、Pavol Jakubec、Paul Turner、Darren J. Dixon

  DOI：10.1021/ol401784h

  日期：2013.9.6

  A highly enantioselective hydroamination/N-sulfonyliminium cyclization cascade is reported using a combination of gold(I) and chiral phosphoric acid catalysts. An initial 5-exo-dig hydroamination and a subsequent phosphoric acid catalyzed cyclization process provide access to complex sulfonamide scaffolds in excellent yield and high enantiocontrol. The method can be extended to lactam derivatives, with excellent yields and enantiomeric excesses of up to 93% ee.