1-(1H-indol-3-yl)-2-phenylmethanesulfonyl-1,2,3,4-tetrahydroisoquinoline | 1123754-78-8

• 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: 1-(1H-indol-3-yl)-2-phenylmethanesulfonyl-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 2-benzylsulfonyl-1-(1H-indol-3-yl)-3,4-dihydro-1H-isoquinoline
• CAS: 1123754-78-8
• 化学式: C₂₄H₂₂N₂O₂S
• 分子量: 402.517
• InChiKey: FCZMDDWDVXBQKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-((R)-2-phenylmethanesulfonyl-1,2,3,4-tetrahydroisoquinolin-1-yl)indole-1-carboxylic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以56%的产率得到1-(1H-indol-3-yl)-2-phenylmethanesulfonyl-1,2,3,4-tetrahydroisoquinoline
  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

文献信息

• Copper-catalyzed aerobic decarboxylative coupling between cyclic α-amino acids and diverse C–H nucleophiles with low catalyst loading
  作者：Jing Guo、Ying Xie、Qiao-Lei Wu、Wen-Tian Zeng、Albert S. C. Chan、Jiang Weng、Gui Lu

  DOI：10.1039/c8ra02340a

  日期：——

  An aerobic decarboxylative cross-coupling of α-amino acids with diverse C–H nucleophiles has been realized using Cu2(OH)2CO3 (1 mol%) as the catalyst under air. This protocol enables highly efficient formation of various C(sp3)–C(sp3), C(sp3)–C(sp2) and C(sp3)–C(sp) bonds under simple conditions without the use of any ligand or extra oxidant, providing a practical approach to numerous nitrogen-containing

  使用Cu 2 (OH) 2 CO 3 (1 mol%)作为催化剂在空气下实现了α-氨基酸与多种C-H亲核试剂的需氧脱羧交叉偶联。该协议能够在简单的条件下高效形成各种 C(sp 3 )–C(sp 3 )、C(sp 3 )–C(sp 2 ) 和 C(sp 3 )–C(sp) 键，而无需使用任何配体或额外的氧化剂，为许多含氮化合物提供了一种实用的方法，产率从良好到极好。克级实验和 Rad51 抑制剂的三步合成也证明了效率和实用性。
• DISULFONATE STILBENES FOR USE IN THE TREATMENT OF PROLIFERATIVE DISEASES
  申请人：UNIVERSITÉ DE NANTES

  公开号：US20220016068A1

  公开（公告）日：2022-01-20

  Compounds of general formula: wherein R 0A and R 0B are independently selected from hydrogen and pharmaceutically acceptable cations; and R A and R B are identical and selected from amide, carbamate, sulphonamide, azido, cyano and halide. Also, a pharmaceutical composition including one of the compounds. The composition may also include another active ingredient, especially an antineoplastic agent. Further a compound or a composition for use as a medicament, especially a compound or a composition for use in the treatment of a proliferative disease such as for example cancer.