2-amino-6-chloro-3,3-dimethyl-3,4-dihydronaphthalen-1(2H)-one hydrochloride | 1394018-03-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2-amino-6-chloro-3,3-dimethyl-3,4-dihydronaphthalen-1(2H)-one hydrochloride
• CAS: 1394018-03-1
• 化学式: C₁₂H₁₄ClNO*ClH
• 分子量: 260.163
• InChiKey: DIWNWQLNNBGYOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.85
• 重原子数：
  16.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  43.09
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2-amino-6-chloro-3,3-dimethyl-3,4-dihydronaphthalen-1(2H)-one hydrochloride 、 5-异丙基-3-甲基异噁唑-4-羧酸 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.08h， 以14%的产率得到N-(6-chloro-3,3-dimethyl-1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl)-5-isopropyl-3-methylisoxazole-4-carboxamide
  参考文献：
  名称：

  N-1-Alkyl-2-oxo-2-aryl amides as novel antagonists of the TRPA1 receptor

  摘要：

  A series of potent antagonists of the ion channel transient receptor potential A1 (TRPA1) was developed by modifying lead structure 16 that was discovered by high-throughput screening. Based on lead compound 16, a SAR was established, showing a narrow region at the nitro-aromatic R-1 moiety and at the warhead, while the R-2 side had a much wider scope including ureas and carbamates. Compound 16 inhibits Ca2+-activated TRPA1 currents reversibly in whole cell patch clamp experiments, indicating that under in vivo conditions, it does not react covalently, despite its potentially electrophilic ketone. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.07.032
• 作为产物：
  描述：

  (E)-6-chloro-3,3-dimethyl-3,4-dihydronaphthalen-1(2H)-one O-tosyl oxime 在 sodium 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以68%的产率得到2-amino-6-chloro-3,3-dimethyl-3,4-dihydronaphthalen-1(2H)-one hydrochloride
  参考文献：
  名称：

  N-1-Alkyl-2-oxo-2-aryl amides as novel antagonists of the TRPA1 receptor

  摘要：

  A series of potent antagonists of the ion channel transient receptor potential A1 (TRPA1) was developed by modifying lead structure 16 that was discovered by high-throughput screening. Based on lead compound 16, a SAR was established, showing a narrow region at the nitro-aromatic R-1 moiety and at the warhead, while the R-2 side had a much wider scope including ureas and carbamates. Compound 16 inhibits Ca2+-activated TRPA1 currents reversibly in whole cell patch clamp experiments, indicating that under in vivo conditions, it does not react covalently, despite its potentially electrophilic ketone. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.07.032