5-cyano-2-methylindan-1-one | 98709-84-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 5-cyano-2-methylindan-1-one
• 英文别名: 2-methyl-1-oxo-2,3-dihydro-1H-indene-5-carbonitrile；5-cyano-2-methyl-1-indanone；2-methyl-1-oxo-2,3-dihydroindene-5-carbonitrile
• CAS: 98709-84-3
• 化学式: C₁₁H₉NO
• 分子量: 171.199
• InChiKey: ZQDXQHNPTXNWQI-UHFFFAOYSA-N

物化性质

• 熔点：
  90-91 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  324.6±31.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-cyano-2-methylindan-1-one 在 sodium hydride 、 一水合肼 作用下， 以 溶剂黄146 为溶剂， 反应 24.67h， 生成 7-cyano-4,4a-dihydro-4a-methyl-5H-indeno<1,2-c>pyridazin-3(2H)-one
  参考文献：
  名称：

  Inotropic, vasodilator and low Km, cAMP-selective, cGMP-inhibited phosphodiesterase (PDE III) inhibitory activities of 4a-methyl-4,4a-dihydro-5H-indeno[1,2-c]pyridazin-3(2H)-ones and 4a-methyl-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3(2H)-ones

  摘要：

  Novel 7-substituted-4,4a-dihydro-4a-methyl-5H-indenol[1,2-c]pyridazin-3[2H]-ones and 8-substituted-4a-methylbenzo[h]cinnolin-3[2H]-ones have been synthesized and their PDE III inhibitory, inotropic and vasodilator potencies compared with those of their normethyl analogues and their bicyclic 4,5-dihydro-6-phenylpyridazinone analogues. The structure-activity relationships of the tricyclic pyridazinones differ from those of bicyclic pyridazinones mainly in respect of the effect of introducing the methyl group into the pyridazinone ring. Whilst in the 4,5-dihydro-6-phenylpyridazin-3(2H)-ones, introduction of a 5-methyl group has been widely reported to lead to compounds of significantly greater potency, the novel tricyclic 4a-methylpyridazinones showed similar levels of inotropic, vasodilator and PDE III inhibitory potency to their normethyl analogues. Possible reasons for this difference in behaviour are discussed.

  DOI：

  10.1016/0223-5234(90)90196-a
• 作为产物：
  描述：

  4-acetyl-3-vinylbenzonitrile 在 磷酸二苯酯 、 chlorobis(ethylene)rhodium(I) dimer 、 3-methyl-5-(p-methylphenyl)pyridin-2-amine 、 三苯基膦 作用下， 以 氯苯 为溶剂， 反应 48.0h， 以60%的产率得到5-cyano-2-methylindan-1-one
  参考文献：
  名称：

  通过 C–C 激活启用烯烃的 1,1-插入无应变酮的分子内单碳同系化

  摘要：

  在这里，我们描述了通过烯烃的正式 1,1-插入过程，通过临时导向基团 (TDG) 辅助的 C-C 活化实现的 Rh 催化的无应变芳基酮的分子内单碳同系化的发展。该反应提供了一种独特的方法来获得各种取代的 1-茚满酮。计算机理研究表明，正式的 1,1-插入是通过选择性 C(sp 2 )–C(sp 3 ) 激活和限制 2,1-插入烯烃的转换来实现的，然后是轻松的 β-H 消除和重新插入过程。

  DOI：

  10.1021/acs.orglett.2c00716

文献信息

• Tricyclic pyridazinone compounds
  申请人：Smith Kline & French Laboratories Limited

  公开号：US04755511A1

  公开（公告）日：1988-07-05

  This invention relates to tricyclic pyridazinone compounds, pharmaceutical compositions containing the compounds, and a method of stimulating cardiac activity in a mammal by administering an effective amount of the compound. A compound of the invention is 7-carboxamido-4,4a-dihydro-4a-methyl-[5H]-indeno[1,2-c]-pyridazin-3[2H]-on e.

  这项发明涉及三环吡啶啉酮化合物，含有这些化合物的药物组合物，以及通过给哺乳动物施用有效量的化合物来刺激心脏活动的方法。该发明的一种化合物是7-羧胺基-4,4a-二氢-4a-甲基-[5H]-茚蒽[1,2-c]-吡啶啉-3[2H]-酮。
• Substituted indenyl acetic acids
  申请人：Merck & Co., Inc.

  公开号：US03956363A1

  公开（公告）日：1976-05-11

  New substituted indenyl acetic acids and nontoxic pharmaceutically acceptable amides, esters and salts derived therefrom. The substituted indenyl acetic acids disclosed herein have anit-inflammatory, anti-pyretic and analgesic activity.

  新的取代基茚基乙酸和由此衍生的无毒药学上可接受的酰胺、酯和盐。本文所披露的取代基茚基乙酸具有抗炎、退热和镇痛活性。
• Fused thiadiazines
  申请人：Smith Kline & French Laboratories Limited

  公开号：US04616013A1

  公开（公告）日：1986-10-07

  This invention relates to thiadiazinone derivatives which have inotropic and vasodilator activity. A specific compound of this invention is 7-acetamido-9,9a-dihydroindeno[1,2-e][1,3,4]thiadiazine-2(3H)-one.

  本发明涉及一种具有肌力增强和血管扩张作用的噻二嗪酮衍生物。本发明的一种特定化合物为7-乙酰氨基-9,9a-二氢吲哚[1,2-e][1,3,4]噻二嗪-2(3H)-酮。
• Thiadiazinone compounds, process for their preparation, and pharmaceutical compositions containing them
  申请人：SMITH KLINE & FRENCH LABORATORIES LIMITED

  公开号：EP0145236A2

  公开（公告）日：1985-06-19

  Compounds of the formula (I):- and salts thereof, wherein R' is hydrogen, C1-6 alkyl, halo, cyano, nitro, amino, a group -NHCOR4, a group -COR5, or a group -NHC(NCN)NHR6; wherein R4 is hydrogen, C1-6 alkoxy, C1-6alkyl optionally substituted by phenyl, or R4 is a group NR7R8 wherein R7 and R8 are independently hydrogen, C1-6salkyl or benzyl; R5 is hydroxy, hydrogen, C1-6alkyl, C1-6alkoxy, or a group -NR7R8; and R6 is hydrogen or C1-6alkyl; R2 is hydrogen or C1-4alkyl; R3 is hydrogen or C1-4alkyl; and n is one, and when R3 is hydrogen n can also be two. Processes and intermediates for their preparation are described. Pharmaceutical compositions containing them are described, as is their use as inotropic agents.

  式(I)化合物 及其盐类，其中 R'是氢、C1-6烷基、卤代、氰基、硝基、氨基、基团-NHCOR4、基团-COR5 或基团-NHC(NCN)NHR6；其中 R4 是氢、C1-6烷氧基、任选被苯基取代的 C1-6 烷基，或 R4 是基团 NR7R8，其中 R7 和 R8 独立地是氢、C1-6烷基或苄基；R5是羟基、氢、C1-6烷基、C1-6烷氧基或基团-NR7R8；R6是氢或C1-6烷基；R2是氢或C1-4烷基；R3是氢或C1-4烷基；n是1，当R3是氢时，n也可以是2。 介绍了制备它们的工艺和中间体。描述了含有它们的药物组合物，以及它们作为肌张力剂的用途。
• BAKEWELL, S. J.;COATES, W. J.;COMER, M. B.;REEVES, M. L.;WARRINGTON, B. H+, EUR. J. MED. CHEM., 25,(1990) N, C. 765-774
  作者：BAKEWELL, S. J.、COATES, W. J.、COMER, M. B.、REEVES, M. L.、WARRINGTON, B. H+

  DOI：——

  日期：——