1,1,1-trifluoro-N-(3-methoxyphenyl)methanesulfonamide | 23384-33-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,1,1-trifluoro-N-(3-methoxyphenyl)methanesulfonamide
• 英文别名: N-(3-methoxyphenyl)trifluoromethanesulfonamide；m-trifluoromethanesulfonanisidide；1,1,1-Trifluoro-N-(3-methoxyphenyl)methansulfonamid；M-Meo CF3-methanesulfonanilide
• CAS: 23384-33-0
• 化学式: C₈H₈F₃NO₃S
• 分子量: 255.218
• InChiKey: XOOZVLSFXLIQRS-UHFFFAOYSA-N

物化性质

• 熔点：
  63-65 °C
• 沸点：
  275.3±50.0 °C(Predicted)
• 密度：
  1.498±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  63.8
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,1,1-trifluoro-N-(3-methoxyphenyl)methanesulfonamide 在 正丁基锂 、 4-(三氟甲基)吗啉 作用下， 以 1,4-二氧六环 、 正己烷 、 二氯甲烷 为溶剂， 反应 2.08h， 生成 N-(3-(3,6-dibromo-9H-carbazol-9-yl)-2-fluoropropyl)-1,1,1-trifluoro-N-(3-methoxyphenyl)methanesulfonamide
  参考文献：
  名称：

  Development of a scalable synthesis of P7C3-A20, a potent neuroprotective agent

  摘要：

  A scalable synthesis of the neuroprotective agent P7C3-A20 is described. The synthesis has provided hundred-gram batches of the final compound for biological evaluation in rodents and primates. The synthesis can be performed without chromatographic purification of intermediates or the final product. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.06.024
• 作为产物：
  描述：

  三氟甲磺酸酐 、 间氨基苯甲醚 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以77%的产率得到1,1,1-trifluoro-N-(3-methoxyphenyl)methanesulfonamide
  参考文献：
  名称：

  Pro-Neurogenic Compounds

  摘要：

  本发明公开了刺激神经发生（例如，产后神经发生，包括产后海马和下丘脑神经发生）和/或保护神经细胞免于细胞死亡的化合物和方法。体内活性测试表明，这些化合物可能在精神神经疾病和/或神经退行性疾病中具有治疗益处，例如精神分裂症、重度抑郁症、双相情感障碍、正常衰老、癫痫、创伤性脑损伤、创伤后应激障碍、帕金森病、阿尔茨海默病、唐氏综合症、脊髓小脑共济失调、肌萎缩侧索硬化症、亨廷顿病、中风、放射治疗、慢性压力、滥用神经活性药物、视网膜退化、脊髓损伤、周围神经损伤、与各种情况相关的生理体重减轻，以及与正常衰老、化疗等相关的认知衰退。

  公开号：

  US20140057900A1

文献信息

• Synthesis of substituted quinolines by the electrophilic cyclization of n-(2-alkynyl)anilines
  作者：Xiaoxia Zhang、Tuanli Yao、Marino A. Campo、Richard C. Larock

  DOI：10.1016/j.tet.2009.12.012

  日期：2010.2

  A wide variety of substituted quinolines are readily synthesized under mild reaction conditions by the 6-endo-dig electrophilic cyclization of N-(2-alkynyl)anilines by ICl, I2, Br2, PhSeBr, and p-O2NC6H4SCl. The reaction affords 3-halogen-, selenium- and sulfur-containing quinolines in moderate to good yields in the presence of various functional groups. Analogous quinolines bearing a hydrogen in the

  通过 ICl、I 2、Br 2、PhSeBr 和p -O 2 NC 6 H对N -(2-炔基)苯胺进行6-内位亲电环化，可以在温和的反应条件下轻松合成各种取代的喹啉。4 SCl。该反应在各种官能团存在下以中等至良好的产率提供含3-卤素、硒和硫的喹啉。通过Hg(OTf) 2催化这些相同的炔基苯胺的闭环，已经合成了在3-位带有氢的类似喹啉。
• Reactions of Trifluoromethanesulfonyl Azide with Aromatic Compounds
  作者：Nobumasa Kamigata、Kazutoshi Yamamoto、Osamu Kawakita、Kiyoyuki Hikita、Haruo Matsuyama、Masato Yoshida、Michio Kobayashi

  DOI：10.1246/bcsj.57.3601

  日期：1984.12

  of trifluoromethanesulfonyl azide in solvents composed of 1:1 mixtures of benzene and substituted benzenes gives trifluoromethanesulfonanilide and substituted trifluoromethanesulfonanilides. The isomer ratios, the total rate ratios, and the partial rate factors for the sulfonamidation have been determined. By the intramolecular and intermolecular selectivities, the reaction mechanism involving trifluoromethanesulfonyl

  三氟甲磺酰叠氮化物在由苯和取代苯的 1:1 混合物组成的溶剂中热解得到三氟甲磺酰苯胺和取代的三氟甲磺酰苯胺。已经确定了磺酰胺化的异构体比率、总速率比率和部分速率因子。通过分子内和分子间的选择性，讨论了涉及三氟甲磺酰基氮烯中间体的反应机理。
• Methods for Treating Parkinson's Disease Using Pro-Neurogenic Compounds
  申请人：UNIVERSITY OF TEXAS SYSTEM BOARD OF REGENTS OF THE

  公开号：US20130184271A1

  公开（公告）日：2013-07-18

  This technology relates generally to compounds and methods for stimulating neurogenesis (e.g., post-natal neurogenesis, including post-natal hippocampal and hypothalamic neurogenesis) and/or protecting neuronal cell from cell death. Various compounds are disclosed herein. In vivo activity tests suggest that these compounds may have therapeutic benefits in neuropsychiatric and/or neurodegenerative diseases such as schizophrenia, major depression, bipolar disorder, normal aging, epilepsy, traumatic brain injury, post-traumatic stress disorder, Parkinson's disease, Alzheimer's disease, Down syndrome, spinocerebellar ataxia, amyotrophic lateral sclerosis, Huntington's disease, stroke, radiation therapy, chronic stress, abuse of a neuro-active drug, retinal degeneration, spinal cord injury, peripheral nerve injury, physiological weight loss associated with various conditions, as well as cognitive decline associated with normal aging, chemotherapy, and the like.

  本技术通常涉及化合物和方法，用于刺激神经发生新生（例如，出生后神经发生新生，包括出生后海马和下丘脑神经发生新生）和/或保护神经细胞免受细胞死亡。本文介绍了各种化合物。体内活性测试表明，这些化合物可能在神经精神疾病和/或神经退行性疾病（如精神分裂症、重度抑郁症、躁郁症、正常衰老、癫痫、创伤性脑损伤、创伤后应激障碍、帕金森病、阿尔茨海默病、唐氏综合症、脊髓小脑性共济失调、肌萎缩性侧索硬化症、亨廷顿病、中风、放射治疗、慢性应激、神经活性药物滥用、视网膜退化、脊髓损伤、外周神经损伤、与各种疾病相关的生理性体重下降以及与正常衰老、化疗等相关的认知衰退中具有治疗益处。
• Methods for treating Parkinson's disease using pro-neurogenic compounds
  申请人：Board of Regents of The University of Texas System

  公开号：US08877797B2

  公开（公告）日：2014-11-04

  This technology relates generally to compounds and methods for stimulating neurogenesis (e.g., post-natal neurogenesis, including post-natal hippocampal and hypothalamic neurogenesis) and/or protecting neuronal cell from cell death. Various compounds are disclosed herein. In vivo activity tests suggest that these compounds may have therapeutic benefits in neuropsychiatric and/or neurodegenerative diseases such as schizophrenia, major depression, bipolar disorder, normal aging, epilepsy, traumatic brain injury, post-traumatic stress disorder, Parkinson's disease, Alzheimer's disease, Down syndrome, spinocerebellar ataxia, amyotrophic lateral sclerosis, Huntington's disease, stroke, radiation therapy, chronic stress, abuse of a neuro-active drug, retinal degeneration, spinal cord injury, peripheral nerve injury, physiological weight loss associated with various conditions, as well as cognitive decline associated with normal aging, chemotherapy, and the like.

  这项技术通常涉及化合物和方法，用于刺激神经发生（例如，产后神经发生，包括产后海马和下丘脑神经发生）和/或保护神经细胞免受细胞死亡的影响。本文介绍了各种化合物。体内活性测试表明，这些化合物可能在神经精神疾病和/或神经退行性疾病（例如精神分裂症、重度抑郁症、躁郁症、正常衰老、癫痫、创伤性脑损伤、创伤后应激障碍、帕金森病、阿尔茨海默病、唐氏综合症、脊髓小脑性共济失调、肌萎缩性侧索硬化症、亨廷顿病、中风、放射治疗、慢性应激、神经活性药物滥用、视网膜退化、脊髓损伤、外周神经损伤以及与正常衰老、化疗等有关的认知下降）方面具有治疗益处。
• Methods for Treating Amyotrophic Lateral Sclerosis Using Pro-Neurogenic Compounds
  申请人：OF TEXAS SYSTEM BOARD OF REGENTS OF THE UNIVERSITY

  公开号：US20130190273A1

  公开（公告）日：2013-07-25

  This technology relates generally to compounds and methods for stimulating neurogenesis (e.g., post-natal neurogenesis, including post-natal hippocampal and hypothalamic neurogenesis) and/or protecting neuronal cell from cell death. Various compounds are disclosed herein. In vivo activity tests suggest that these compounds may have therapeutic benefits in neuropsychiatric and/or neurodegenerative diseases such as schizophrenia, major depression, bipolar disorder, normal aging, epilepsy, traumatic brain injury, post-traumatic stress disorder, Parkinson's disease, Alzheimer's disease, Down syndrome, spinocerebellar ataxia, amyotrophic lateral sclerosis, Huntington's disease, stroke, radiation therapy, chronic stress, abuse of a neuro-active drug, retinal degeneration, spinal cord injury, peripheral nerve injury, physiological weight loss associated with various conditions, as well as cognitive decline associated with normal aging, chemotherapy, and the like.

  该技术通常涉及化合物和方法，用于刺激神经发生（例如，产后神经发生，包括产后海马和下丘脑神经发生）和/或保护神经细胞免受细胞死亡的影响。本文披露了各种化合物。体内活性测试表明，这些化合物可能对神经精神疾病和/或神经退行性疾病（如精神分裂症、重度抑郁症、躁郁症、正常衰老、癫痫、创伤性脑损伤、创伤后应激障碍、帕金森病、阿尔茨海默病、唐氏综合症、脊髓小脑性共济失调、肌萎缩性侧索硬化症、亨廷顿病、中风、放射治疗、慢性应激、滥用神经活性药物、视网膜退化、脊髓损伤、周围神经损伤、与各种情况相关的生理性体重减轻以及与正常衰老、化疗等相关的认知衰退）具有治疗益处。