(S)-1-(1H-indol-3-yl)-1,2,3,4-tetrahydro-isoquinolin | 1123754-96-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: (S)-1-(1H-indol-3-yl)-1,2,3,4-tetrahydro-isoquinolin
• 英文别名: (1S)-1-(1H-indol-3-yl)-1,2,3,4-tetrahydroisoquinoline
• CAS: 1123754-96-0
• 化学式: C₁₇H₁₆N₂
• 分子量: 248.327
• InChiKey: OVZZYKLLIUWFKD-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  27.8
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-1-(1H-indol-3-yl)-1,2,3,4-tetrahydro-isoquinolin 、 苄磺酰氯 在 4-二甲氨基吡啶 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到(S)-1-(1H-indol-3-yl)-2-phenylmethanesulfonyl-1,2,3,4-tetrahydro-isoquinolin
  参考文献：
  名称：

  Stereoselective Synthesis of Chiral IBR2 Analogues

  摘要：

  Two stereoselective routes were developed to synthesize optically pure IBR2 analogues 1-16. The first features addition of N-Boc-3-bromoindole 26 to the sulfinamide 25, providing a 1: 1 ratio of the separable diasteroisomers 27 and 28 in good yield. In a straightforward fashion, the sulfinamides 27 and 28 were conveniently converted into the key amines 39 and 47 over 8 steps, respectively, from which a series of 3,4-dihydroisoquinolinyl IBR2 analogues 1-14 containing fluorinated and trifluoromethylated benzyl groups were prepared. Another route highlights the highly enantioselective addition of indole to the sulfonyl amide 50 with bifunctional aminothioureas 57 and 58 as catalysts. After the reaction conditions were optimized, the desired sulfonyl amides (R)-55 and (S)-55 were obtained in 99% ee and 98% ee, respectively. Acylation of (R)-55 and (S)-55 separately and subsequent allylation gave compounds 60 and 63, respectively, which were further subjected to RCM to furnish compounds 61 and 64 and, after removal of the Boc groups, the desired IBR2 analogues 15 and 16.

  DOI：

  10.1021/jo802607f
• 作为产物：
  描述：

  2-甲基-2-丙基1-[(2-甲基-2-丙基)氧基]-2(1H)-异喹啉羧酸酯 在 三甲基氯硅烷 、 (S)-3,3'-bis(9-anthracenyl)-1,1′-binaphthyl-2,2′-diyl hydrogenphosphate 、 四丁基氟化铵 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 对二甲苯 为溶剂， 反应 1.0h， 生成 (S)-1-(1H-indol-3-yl)-1,2,3,4-tetrahydro-isoquinolin
  参考文献：
  名称：

  异喹啉的对映选择性脱芳香化

  摘要：

  C 1取代的四氢异喹啉和1,2-二氢异喹啉构成一个重要的基团，并且是在许多天然产物和药物中发现的有趣的结构基序。在此情况下，实现了磷酸催化的异喹啉对映选择性脱芳芳基化，为手性二氢异喹啉在C1位上带有吲哚取代基提供了良好的结果（产率高达99％和ee达97％）。该反应具有温和的反应条件和操作简便性，这使其成为发现生物学上有趣的α-吲哚异喹啉的一种有吸引力的方法。

  DOI：

  10.1021/acscatal.6b01693

文献信息

• Enantioselective Dearomative Arylation of Isoquinolines
  作者：Ming Zhang、Wangsheng Sun、Gongming Zhu、Guangjun Bao、Bangzhi Zhang、Liang Hong、Min Li、Rui Wang

  DOI：10.1021/acscatal.6b01693

  日期：2016.8.5

  important group and are interesting structural motifs found in many natural products and pharmaceuticals. In this context, a phosphoric-acid-catalyzed enantioselective dearomative arylation of isoquinolines was realized, providing the chiral dihydroisoquinolines with indole substituents at the C1-position in good results (up to >99% yield and 97% ee). The reaction features mild reaction conditions

  C 1取代的四氢异喹啉和1,2-二氢异喹啉构成一个重要的基团，并且是在许多天然产物和药物中发现的有趣的结构基序。在此情况下，实现了磷酸催化的异喹啉对映选择性脱芳芳基化，为手性二氢异喹啉在C1位上带有吲哚取代基提供了良好的结果（产率高达99％和ee达97％）。该反应具有温和的反应条件和操作简便性，这使其成为发现生物学上有趣的α-吲哚异喹啉的一种有吸引力的方法。
• Stereoselective Synthesis of Chiral IBR2 Analogues
  作者：Xiao-Long Qiu、Jiewen Zhu、Guikai Wu、Wen-Hwa Lee、A. Richard Chamberlin

  DOI：10.1021/jo802607f

  日期：2009.3.6

  Two stereoselective routes were developed to synthesize optically pure IBR2 analogues 1-16. The first features addition of N-Boc-3-bromoindole 26 to the sulfinamide 25, providing a 1: 1 ratio of the separable diasteroisomers 27 and 28 in good yield. In a straightforward fashion, the sulfinamides 27 and 28 were conveniently converted into the key amines 39 and 47 over 8 steps, respectively, from which a series of 3,4-dihydroisoquinolinyl IBR2 analogues 1-14 containing fluorinated and trifluoromethylated benzyl groups were prepared. Another route highlights the highly enantioselective addition of indole to the sulfonyl amide 50 with bifunctional aminothioureas 57 and 58 as catalysts. After the reaction conditions were optimized, the desired sulfonyl amides (R)-55 and (S)-55 were obtained in 99% ee and 98% ee, respectively. Acylation of (R)-55 and (S)-55 separately and subsequent allylation gave compounds 60 and 63, respectively, which were further subjected to RCM to furnish compounds 61 and 64 and, after removal of the Boc groups, the desired IBR2 analogues 15 and 16.