1-methyl-5-vinyl-1H-indazole | 1430235-17-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 英文名称: 1-methyl-5-vinyl-1H-indazole
• 英文别名: 5-Ethenyl-1-methylindazole
• CAS: 1430235-17-8
• 化学式: C₁₀H₁₀N₂
• 分子量: 158.203
• InChiKey: SELIONDMQXPLEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-methyl-5-vinyl-1H-indazole 、 二苯基硅烷 在 bis(1,5-cyclooctadiene)nickel (0) 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以84%的产率得到5-(2-(diphenylsilyl)ethyl)-1-methyl-1H-indazole
  参考文献：
  名称：

  Fused Heteroaromatic Dihydrosiloles: Synthesis and Double-Fold Modification

  摘要：

  An efficient method for the synthesis of fused heteroaromatic dihydrosiloles via Ni-catalyzed hydrosilylation/intramolecular Ir-catalyzed dehydrogenative coupling of the Si-H bond with the heteroaromatic C-H bond has been developed. The method is efficient for both electron-deficient and -rich heterocycles. It exhibits high functional group tolerance and good regioselectivity. Fused heteroaromatic dihydrosiloles can be smoothly halogenated and then oxidized or arylated. Application of these transformations allows obtaining highly functionallzed heteroaromatic structures. A gram-scale synthesis of dihydropyridinosilole has also been accomplished using reduced amounts of Ni- and Ir-catalysts.

  DOI：

  10.1021/ol400977r
• 作为产物：
  描述：

  5-溴吲唑 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 sodium hydride 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.17h， 生成 1-methyl-5-vinyl-1H-indazole
  参考文献：
  名称：

  通过1,3-偶极环加成反应合成衍生自乙烯基吲哚/吲唑的螺吡咯烷类似物。

  摘要：

  通过一锅多组分合成已经完成了一系列新的含有吡咯/吲唑部分作为侧链的螺并吡咯烷化合物。该方法使用了N-烷基乙烯基吲哚/吲唑与由环/无环氨基酸原位制备的偶氮甲亚胺之间的1,3-偶极环加成反应。1,3-偶极环加成反应在热条件下有效进行，从而提供区域和立体有规的环状加合物。

  DOI：

  10.3762/bjoc.12.288

文献信息

• Nickel-catalyzed anti-Markovnikov hydroarylation of alkenes
  作者：Julia Nguyen、Andrea Chong、Gojko Lalic

  DOI：10.1039/c8sc05445b

  日期：——

  We have developed a nickel-catalyzed hydroarylation of alkenes using aryl halides as coupling partners. Excellent anti-Markovnikov selectivity is achieved with aryl-substituted alkenes and enol ethers. We also show that hydroarylation occurs with alkyl substituted alkenes to yield linear products. Preliminary examination of the reaction mechanism suggests irreversible hydrometallation as the selectivity

  我们开发了一种镍催化的烯烃加氢芳基化方法，使用芳基卤化物作为偶联伙伴。使用芳基取代的烯烃和烯醇醚可实现出色的抗马可夫尼科夫选择性。我们还表明，烷基取代的烯烃发生加氢芳基化，产生线性产物。反应机理的初步研究表明不可逆的加氢金属化是加氢芳基化的选择性决定步骤。
• Asymmetric Copper Hydride-Catalyzed Markovnikov Hydrosilylation of Vinylarenes and Vinyl Heterocycles
  作者：Michael W. Gribble、Michael T. Pirnot、Jeffrey S. Bandar、Richard Y. Liu、Stephen L. Buchwald

  DOI：10.1021/jacs.6b13029

  日期：2017.2.15

  We report a highly enantioselective CuH-catalyzed Markovnikov hydrosilylation of vinylarenes and vinyl heterocycles. This method has a broad scope and enables both the synthesis of isolable silanes and the conversion of crude products to chiral alcohols. Density functional theory calculations support a mechanism proceeding by hydrocupration followed by sigma-bond metathesis with a hydrosilane.
• METHOD FOR PREDICTING THERAPEUTIC EFFECT OF LSD1 INHIBITOR BASED ON EXPRESSION OF INSM1
  申请人：TAIHO PHARMACEUTICAL CO., LTD.

  公开号：US20200190175A1

  公开（公告）日：2020-06-18

  A method for predicting a therapeutic effect of a chemotherapy using an antitumor agent comprising an LSD1 inhibitor in a cancer patient based on an expression level of INSM1 in a sample containing tumor cells isolated from the cancer patient.
• NOVEL BIPHENYL COMPOUND OR SALT THEREOF
  申请人：TAIHO PHARMACEUTICAL CO., LTD.

  公开号：US20210179634A1

  公开（公告）日：2021-06-17

  The present invention provides a compound represented by Formula (I) or a salt thereof; an LSD1 inhibitor that contains the compound or a salt thereof as an active ingredient; a pharmaceutical composition that contains the compound or a salt thereof; and an antitumor agent that contains the compound or a salt thereof as an active ingredient.
• [EN] NOVEL BIPHENYL COMPOUND OR SALT THEREOF<br/>[FR] NOUVEAU COMPOSÉ DE BIPHÉNYLE OU UN SEL DE CELUI-CI<br/>[JA] 新規なビフェニル化合物又はその塩
  申请人：TAIHO PHARMACEUTICAL CO LTD

  公开号：WO2017090756A1

  公开（公告）日：2017-06-01

  一般式（I）で表される化合物又はその塩。当該化合物又はその塩を有効成分とするＬＳＤ１阻害剤。当該化合物又はその塩を含有する医薬組成物。当該化合物又はその塩を有効成分とする抗腫瘍剤。