2-甲基-2,4,6,7-四氢-5H-吲唑-5-酮 | 904664-22-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-甲基-2,4,6,7-四氢-5H-吲唑-5-酮
• 英文名称: 2-methyl-2,4,6,7-tetrahydro-5H-indazol-5-one
• 英文别名: 2-methyl-2,4,6,7-tetrahydro-indazol-5-one；2-methyl-6,7-dihydro-2H-indazol-5(4H)-one；2-methyl-6,7-dihydro-4H-indazol-5-one
• CAS: 904664-22-8
• 化学式: C₈H₁₀N₂O
• 分子量: 150.18
• InChiKey: UWFKGBFHSNIJOS-UHFFFAOYSA-N

物化性质

• 熔点：
  87-90 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  313.5±42.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-甲基-2,4,6,7-四氢-5H-吲唑-5-酮 、 吲哚 在 正丁基锂 、 二氧化碳 、 叔丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 正戊烷 为溶剂， 反应 4.75h， 以58%的产率得到5-(1H-indol-2-yl)-2-methyl-6,7-dihydro-1H-indazo-5-ol
  参考文献：
  名称：

  区域选择性合成2-甲基-2-5,6,11,12,13-六氢4H吲哚并[5,4-a]吡咯并[3,4-c]咔唑-4-

  摘要：

  2-甲基-2-5,6,11,12,13-六氢4H吲哚并[5,4-a]吡咯并[3,4-c]咔唑-4-酮是利用区域选择性Diels-Alder反应与5合成的-（1H-吲哚-2-基）-2-甲基-6,7-二氢-2H-吲唑和顺式-β-氰基丙烯酸乙酯。乙酸和YtBr 3是区域选择性Diels-Alder反应的最佳溶剂和催化剂。该化学方法用于合成新型8-嘧啶氧基-2,5,6,11,12,13-六氢4H吲哚并[5,4-a]吡咯并[3,4-c]咔唑-4-。被发现是DLK的有效抑制剂。J.杂环化​​学，（2009）。

  DOI：

  10.1002/jhet.200
• 作为产物：
  描述：

  1,4-环己二酮单乙二醇缩酮 在 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 反应 4.0h， 生成 2-甲基-2,4,6,7-四氢-5H-吲唑-5-酮
  参考文献：
  名称：

  Structure determination ofN-methyl-tetrahydro-5H-indazol-5-ones

  摘要：

  Abstractmagnified imageThis paper communicates the (regio) synthesis and a convenient NMR structural assignment method for N‐methyl‐tetrahydro‐5H‐indazol‐5‐one isomers. The cyclization reaction of 7‐(hydroxymethylene)‐1,4‐dioxaspiro[4,5]decan‐8‐one (3) with methylhydrazine yields, after de‐protection predominately the N‐2 methyl isomer 2. Analysis of the product ratio and structural assignments are based on NMR data including NOE difference experiments and subsequently confirmed with X‐ray crystallography. These findings are in sharp contrast with the literature. The experimental conditions used to optimize the synthesis of the individual isomers are discussed.

  DOI：

  10.1002/jhet.5570430328

文献信息

• [EN] PYRAZOLO-TRIAZINE AND/OR PYRAZOLO-PYRIMIDINE DERIVATIVES AS SELECTIVE INHIBITOR OF CYCLIN DEPENDENT KINASE<br/>[FR] DÉRIVÉS DE PYRAZOLO-TRIAZINE ET/OU DE PYRAZOLO-PYRIMIDINE EN TANT QU'INHIBITEURS SÉLECTIFS DE KINASE DÉPENDANTE DE LA CYCLINE
  申请人：QURIENT CO LTD

  公开号：WO2019197549A1

  公开（公告）日：2019-10-17

  The present invention relates to pyrazolo[1,5-a][1,3,5]triazine and pyrazolo[l,5-a]pyrimidine derivatives and/or pharmaceutically acceptable salts thereof, the use of these derivatives as pharmaceutically active agents, especially for the prophylaxis and/or treatment of cell proliferative diseases, inflammatory diseases, immunological diseases, cardiovascular diseases and infectious diseases. Furthermore, the present invention is directed towards pharmaceutical compositions containing at least one of the pyrazolo[1,5-a][1,3,5]triazine and pyrazolo[1,5-a]pyrimidine derivatives and/or pharmaceutically acceptable salts thereof.

  本发明涉及吡唑并[1,5-a][1,3,5]三嗪和吡唑[1,5-a]嘧啶衍生物和/或其药用可接受盐，以及这些衍生物作为药用活性剂的用途，特别是用于预防和/或治疗细胞增殖性疾病、炎症性疾病、免疫性疾病、心血管疾病和传染病。此外，本发明还涉及含有至少一种吡唑并[1,5-a][1,3,5]三嗪和吡唑[1,5-a]嘧啶衍生物和/或其药用可接受盐的药物组合物。
• Regiospecific synthesis of 5-(1<i>H</i>-indol-2-yl)-1- and 2-methyl-6,7-dihydro-2<i>H</i>-indazole isomers
  作者：Reddeppareddy Dandu、Ming Tao、Kurt A. Josef、Edward R. Bacon、Robert L. Hudkins

  DOI：10.1002/jhet.5570440225

  日期：2007.3

  A regiospecific approach to each N-methyl-5-(1H-indol-2-yl)-6,7-dihydro-2H-indazole isomer is reported. The 1-methyl isomer 1 was prepared from 5-bromo-1-methyl-6,7-dihydro-1H-indazole 3 and indole-2-boronate 5 by palladium catalyzed Suzuki coupling. The 2-methyl regioisomer 2 was synthesized via addition of lithium (1-carboxylato-1H-indole-2-yl)lithium 6 with 2-methyl-2,4,6,7-tetrahydro-indazol-5-one

  报道了对每种N-甲基-5-（1 H-吲哚-2-基）-6,7-二氢-2 H-吲唑异构体的区域特异性方法。1-甲基异构体1，从5-溴-1-甲基-6,7-二氢制备ħ -吲唑3和吲哚-2-硼酸酯5通过钯催化的Suzuki偶联。2-甲基区域异构体2的合成是通过添加（1-羧基-lato- 1 H-吲哚-2-基）锂6与2-甲基-2,4,6,7-四氢吲哚-5-酮8，然后由酸催化脱水。
• Regioselective synthesis of 2-methyl-2,5,6,11,12,13-hexahydro 4H indazolo[5,4-a]pyrrolo[3,4-c]carbazole-4-ones
  作者：Ming Tao、Chung Ho Park、Kurt Josef、Robert L. Hudkins

  DOI：10.1002/jhet.200

  日期：2009.11

  13‐hexahydro 4H indazolo[5,4‐a]pyrrolo[3,4‐c]carbazole‐4‐one was synthesized utilizing a regioselective Diels‐Alder reaction with 5‐(1H‐indol‐2‐yl)‐2‐methyl‐6,7‐dihydro‐2H‐indazole and ethyl cis‐β‐cyanoacrylate. Acetic acid and YtBr3 were the best solvent and catalyst for the regioselective Diels‐Alder reaction. The chemistry was used to synthesize novel 8‐pyrimidinyloxy‐2,5,6,11,12,13‐hexahydro 4H

  2-甲基-2-5,6,11,12,13-六氢4H吲哚并[5,4-a]吡咯并[3,4-c]咔唑-4-酮是利用区域选择性Diels-Alder反应与5合成的-（1H-吲哚-2-基）-2-甲基-6,7-二氢-2H-吲唑和顺式-β-氰基丙烯酸乙酯。乙酸和YtBr 3是区域选择性Diels-Alder反应的最佳溶剂和催化剂。该化学方法用于合成新型8-嘧啶氧基-2,5,6,11,12,13-六氢4H吲哚并[5,4-a]吡咯并[3,4-c]咔唑-4-。被发现是DLK的有效抑制剂。J.杂环化​​学，（2009）。
• Structure determination of<i>N</i>-methyl-tetrahydro-5<i>H</i>-indazol-5-ones
  作者：Kurt A. Josef、Reddeppareddy Dandu、Ming Tao、Robert L. Hudkins

  DOI：10.1002/jhet.5570430328

  日期：2006.5

  Abstractmagnified imageThis paper communicates the (regio) synthesis and a convenient NMR structural assignment method for N‐methyl‐tetrahydro‐5H‐indazol‐5‐one isomers. The cyclization reaction of 7‐(hydroxymethylene)‐1,4‐dioxaspiro[4,5]decan‐8‐one (3) with methylhydrazine yields, after de‐protection predominately the N‐2 methyl isomer 2. Analysis of the product ratio and structural assignments are based on NMR data including NOE difference experiments and subsequently confirmed with X‐ray crystallography. These findings are in sharp contrast with the literature. The experimental conditions used to optimize the synthesis of the individual isomers are discussed.