6-methoxy-8-(2-nitro-propenyl)-2,3-dihydro-1H-3a-aza-cyclopenta[a]indene | 260267-18-3

• 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: 6-methoxy-8-(2-nitro-propenyl)-2,3-dihydro-1H-3a-aza-cyclopenta[a]indene
• 英文别名: 1-(7-methoxy-2,3-dihydro-1H-pyrrolo[1,2-a]indol-9-yl)-2-nitro-1-propene；6-methoxy-4-(2-nitroprop-1-enyl)-2,3-dihydro-1H-pyrrolo[1,2-a]indole
• CAS: 260267-18-3
• 化学式: C₁₅H₁₆N₂O₃
• 分子量: 272.304
• InChiKey: BTEPTHPAEAIDPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  60
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-methoxy-8-(2-nitro-propenyl)-2,3-dihydro-1H-3a-aza-cyclopenta[a]indene 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 2-(6-methoxy-2,3-dihydro-1H-3a-aza-cyclopenta[a]inden-8-yl)-1-methyl-ethylamine
  参考文献：
  名称：

  Enantioselective Synthesis of a PKC Inhibitor via Catalytic C−H Bond Activation

  摘要：

  The syntheses of two biologically active molecules possessing dihydropyrroloindole cores (1 and 2) were completed using rhodium-catalyzed imine-directed CA bond functionalization, with the second of these molecules containing a stereocenter that can be set with 90% ee during cyclization using chiral nonracemic phosphoramidite ligands. Catalytic decarbonylation and direct indole/maleimide coupling provide efficient access to 2.

  DOI：

  10.1021/ol060485h
• 作为产物：
  描述：

  5-甲氧基吲哚-3-甲醛 在 RhCl(PPh₃)3 乙酸铵 、 silica gel 、 potassium carbonate 作用下， 以 正己烷 、 乙酸乙酯 、 丙酮 、 甲苯 、 苯 为溶剂， 反应 20.5h， 生成 6-methoxy-8-(2-nitro-propenyl)-2,3-dihydro-1H-3a-aza-cyclopenta[a]indene
  参考文献：
  名称：

  Enantioselective Synthesis of a PKC Inhibitor via Catalytic C−H Bond Activation

  摘要：

  The syntheses of two biologically active molecules possessing dihydropyrroloindole cores (1 and 2) were completed using rhodium-catalyzed imine-directed CA bond functionalization, with the second of these molecules containing a stereocenter that can be set with 90% ee during cyclization using chiral nonracemic phosphoramidite ligands. Catalytic decarbonylation and direct indole/maleimide coupling provide efficient access to 2.

  DOI：

  10.1021/ol060485h

文献信息

• Pyrroloindoles, pyridoindoles and azepinoindoles as 5-ht2c agonists
  申请人：Vernalis Research Limited

  公开号：US06433175B1

  公开（公告）日：2002-08-13

  A chemical compound of formula (I), wherein n is 1, 2 or 3; R1 and R2 are independently selected from hydrogen and alkyl; R3 is alkyl; R4 to R7 are independently selected from hydrogen, halogen, hydroxy, alkyl, aryl, alkoxy, aryloxy, alkylthio, arylthio, alkylsulfoxyl, alkylsulfonyl, arylsulfoxyl, arylsulfonyl, amino, monoalkylamino, dialkylamino, nitro, cyano, carboxaldehyde, alkylcarbonyl, arylcarbonyl, aminocarbonyl, monoalkylaminocarbonyl, dialkylaminocarbonyl, alkoxycarbonylamino, aminocarbonyloxy, monoalkylaminocarbonyloxy, dialkylaminocarbonyloxy, monoalkylaminocarbonylamino and dialkylaminocarbonylamino, or R5 and R6 together form a carbocyclic or heterocyclic ring, and pharmaceutically acceptable salts and prodrugs thereof, and the use thereof in therapy, particularly for the treatment of disorders of the central nervous system; damage to the central nervous system; cardiovascular disorders; gastrointestinal disorders, diabetes insipidus, and sleep apnea, and particularly for the treatment of obesity

  化学式为（I）的化合物，其中n为1，2或3；R1和R2分别选择氢和烷基；R3为烷基；R4至R7分别选择氢、卤素、羟基、烷基、芳基、烷氧基、芳氧基、烷硫基、芳硫基、烷基亚氧基、烷基磺酰氧基、芳基磺酰氧基、芳基磺酰氧基、氨基、单烷基氨基、双烷基氨基、硝基、氰基、羧醛基、烷基羰基、芳基羰基、氨基羰基、单烷基氨基羰基、双烷基氨基羰基、烷氧羰基氨基、氨基羧酸酯、单烷基氨基羧酸酯、双烷基氨基羧酸酯、单烷基氨基羧酸氧酯、双烷基氨基羧酸氧酯，或R5和R6共同形成一个碳环或杂环，以及其药学上可接受的盐和前药，以及在治疗中的使用，特别是用于治疗中枢神经系统疾病；中枢神经系统损伤；心血管疾病；胃肠道疾病、尿崩症和睡眠呼吸暂停症，特别是用于治疗肥胖症。
• Enantioselective Synthesis of a PKC Inhibitor via Catalytic C−H Bond Activation
  作者：Rebecca M. Wilson、Reema K. Thalji、Robert G. Bergman、Jonathan A. Ellman

  DOI：10.1021/ol060485h

  日期：2006.4.1

  The syntheses of two biologically active molecules possessing dihydropyrroloindole cores (1 and 2) were completed using rhodium-catalyzed imine-directed CA bond functionalization, with the second of these molecules containing a stereocenter that can be set with 90% ee during cyclization using chiral nonracemic phosphoramidite ligands. Catalytic decarbonylation and direct indole/maleimide coupling provide efficient access to 2.