6-甲基-4-硝基-1,3-苯并二硫醇-2-酮 | 62558-21-8

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 中文名称: 6-甲基-4-硝基-1,3-苯并二硫醇-2-酮
• 英文名称: 6-methyl-4-nitrobenzo-1,3-dithiol-2-one
• 英文别名: 6-methyl-4-nitro-1,3-benzodithiole-2-one；6-Methyl-4-nitro-2H-1,3-benzodithiol-2-one；6-methyl-4-nitro-1,3-benzodithiol-2-one
• CAS: 62558-21-8
• 化学式: C₈H₅NO₃S₂
• 分子量: 227.265
• InChiKey: NLZDTOPMALMVGD-UHFFFAOYSA-N

物化性质

• 熔点：
  163-164 °C
• 沸点：
  438.3±55.0 °C(Predicted)
• 密度：
  1.599±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  114
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-甲基-4-硝基-1,3-苯并二硫醇-2-酮 在 氯化铵 、 锌 作用下， 以 乙醇 、 水 为溶剂， 以110 mg的产率得到4-amino-6-methylbenzo-1,3-dithiol-2-one
  参考文献：
  名称：

  Synthesis of benzopentathiepin analogs and their evaluation as inhibitors of the phosphatase STEP

  摘要：

  Striatal-enriched protein tyrosine phosphatase (STEP) is a brain specific protein tyrosine phosphatase that has been implicated in many neurodegenerative diseases, such as Alzheimer's disease. We recently reported the benzopentathiepin TC-2153 as a potent inhibitor of STEP in vitro, cells and animals. Herein, we report the synthesis and evaluation of TC-2153 analogs in order to define what structural features are important for inhibition and to identify positions tolerant of substitution for further study. The trifluoromethyl substitution is beneficial for inhibitor potency, and the amine is tolerant of acylation, and thus provides a convenient handle for introducing additional functionality such as reporter groups. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.01.020
• 作为产物：
  描述：

  4-Methyl-2,6-dinitrophenyl dimethylcarbamodithioate 生成 6-甲基-4-硝基-1,3-苯并二硫醇-2-酮
  参考文献：
  名称：

  RASHEED K.; WARKENTIN J. D., J. ORG. CHEM. , 1977, 42, NO 7, 1265-1266

  摘要：

  DOI：

文献信息

• RASHEED K.; WARKENTIN J. D., J. ORG. CHEM.,1979, 44, NO 2, 267-274
  作者：RASHEED K.、 WARKENTIN J. D.

  DOI：——

  日期：——
• US4084954A
  申请人：——

  公开号：US4084954A

  公开（公告）日：1978-04-18
• US4175186A
  申请人：——

  公开号：US4175186A

  公开（公告）日：1979-11-20
• US4177270A
  申请人：——

  公开号：US4177270A

  公开（公告）日：1979-12-04
• Synthesis of benzopentathiepin analogs and their evaluation as inhibitors of the phosphatase STEP
  作者：Tyler D. Baguley、Angus C. Nairn、Paul J. Lombroso、Jonathan A. Ellman

  DOI：10.1016/j.bmcl.2015.01.020

  日期：2015.3

  Striatal-enriched protein tyrosine phosphatase (STEP) is a brain specific protein tyrosine phosphatase that has been implicated in many neurodegenerative diseases, such as Alzheimer's disease. We recently reported the benzopentathiepin TC-2153 as a potent inhibitor of STEP in vitro, cells and animals. Herein, we report the synthesis and evaluation of TC-2153 analogs in order to define what structural features are important for inhibition and to identify positions tolerant of substitution for further study. The trifluoromethyl substitution is beneficial for inhibitor potency, and the amine is tolerant of acylation, and thus provides a convenient handle for introducing additional functionality such as reporter groups. (C) 2015 Elsevier Ltd. All rights reserved.