5-氟-1-甲基-1H-吲哚-2-甲酰氯 | 168201-49-8

• 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
• 中文名称: 5-氟-1-甲基-1H-吲哚-2-甲酰氯
• 英文名称: 5-fluoro-1-methyl-1H-indole-2-carbonyl chloride
• 英文别名: 5-fluoro-1-methylindole-2-carbonyl chloride
• CAS: 168201-49-8
• 化学式: C₁₀H₇ClFNO
• 分子量: 211.623
• InChiKey: FXTWWNPANWRMKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 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：
  22
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-氟-1-甲基-1H-吲哚-2-甲酰氯 、 乙酸乙酯 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 以618 mg的产率得到ethyl 3-(5-fluoro-1-methyl-1H-indol-2-yl)-3-oxopropanoate
  参考文献：
  名称：

  Catalytic Asymmetric Nazarov Cyclization of Heteroaryl Vinyl Ketones through a Crystallographically Defined Chiral Dinuclear Nickel Complex

  摘要：

  A Ni(NTf2)(2) and tetradentate bisimino-bisquinoline ligand complex catalyzed the enantioselective Nazarov cyclization of heteroaryl vinyl ketones. An X-ray-quality crystal was obtained from a mixture of the Ni complex and the substrate, which was the dinuclear chiral Ni complex. From information regarding the structure of the complex, the substrate was distorted to form a helical shape, and the carbon atoms involved in bond formation were close to each other. In addition, mechanistic studies revealed that the configuration of the olefin moiety was isomerized before bond formation.

  DOI：

  10.1021/acs.orglett.5b02497
• 作为产物：
  描述：

  5-氟-1-甲基-1H-吲哚-2-羧酸 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 5-氟-1-甲基-1H-吲哚-2-甲酰氯
  参考文献：
  名称：

  Catalytic Asymmetric Nazarov Cyclization of Heteroaryl Vinyl Ketones through a Crystallographically Defined Chiral Dinuclear Nickel Complex

  摘要：

  A Ni(NTf2)(2) and tetradentate bisimino-bisquinoline ligand complex catalyzed the enantioselective Nazarov cyclization of heteroaryl vinyl ketones. An X-ray-quality crystal was obtained from a mixture of the Ni complex and the substrate, which was the dinuclear chiral Ni complex. From information regarding the structure of the complex, the substrate was distorted to form a helical shape, and the carbon atoms involved in bond formation were close to each other. In addition, mechanistic studies revealed that the configuration of the olefin moiety was isomerized before bond formation.

  DOI：

  10.1021/acs.orglett.5b02497

文献信息

• Annulation of Indole-2-Carboxamides with Bicycloalkenes Catalyzed by Ru(II) at Room Temperature: An Easy Access to β-Carboline-1-one Derivatives under Mild Conditions
  作者：Gopal Krushna Das Adhikari、Smruti Ranjan Mohanty、Shyam Kumar Banjare、Namrata Prusty、Gajiram Murmu、Ponneri C. Ravikumar

  DOI：10.1021/acs.joc.2c02351

  日期：2023.1.20

  Herein, we report the annulation of indole-2-carboxamides with bicycloalkenes, to synthesize β-carboline-1-one derivatives under mild conditions. The commercially available ruthenium catalyst was used for the reaction. This reaction tolerates a wide range of functional groups and affords a good yield of β-carboline-1-one derivatives. A reversible cyclometalation pathway was found to be operative in

  在此，我们报道了吲哚-2-甲酰胺与双环烯烃的环化反应，在温和条件下合成了 β-咔啉-1-酮衍生物。该反应使用市售的钌催化剂。该反应可容忍各种官能团，并提供高收率的 β-咔啉-1-酮衍生物。发现可逆的环金属化途径在机理研究中起作用。
• THIADIAZOLE DERIVATIVES FOR THE TREATMENT OF NEURODEGENERATIVE DISEASES
  申请人：GRIFFIOEN Gerard

  公开号：US20090054410A1

  公开（公告）日：2009-02-26

  This invention provides specifically substituted 1,2,4-thiadiazole derivatives for use in the treatment of an α-synucleopathy such as Parkinson's disease, diffuse Lewy body disease, traumatic brain injury, amyotrophic lateral sclerosis, Niemann-Pick disease, Hallervorden-Spatz syndrome, Down syndrome, neuroaxonal dystrophy, multiple system atrophy and Alzheimer's disease. This invention also provides various methods for producing such substituted 1,2,4-thiadiazole derivatives.
• US8541406B2
  申请人：——

  公开号：US8541406B2

  公开（公告）日：2013-09-24
• Catalytic Asymmetric Nazarov Cyclization of Heteroaryl Vinyl Ketones through a Crystallographically Defined Chiral Dinuclear Nickel Complex
  作者：Takuya Takeda、Shinji Harada、Atsushi Nishida

  DOI：10.1021/acs.orglett.5b02497

  日期：2015.11.6

  A Ni(NTf2)(2) and tetradentate bisimino-bisquinoline ligand complex catalyzed the enantioselective Nazarov cyclization of heteroaryl vinyl ketones. An X-ray-quality crystal was obtained from a mixture of the Ni complex and the substrate, which was the dinuclear chiral Ni complex. From information regarding the structure of the complex, the substrate was distorted to form a helical shape, and the carbon atoms involved in bond formation were close to each other. In addition, mechanistic studies revealed that the configuration of the olefin moiety was isomerized before bond formation.