4-bromo-7-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene | 928169-39-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 4-bromo-7-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene
• 英文别名: 4-Bromo-7-methoxy-2,2-dimethyl-1,3-dihydroindene
• CAS: 928169-39-5
• 化学式: C₁₂H₁₅BrO
• 分子量: 255.155
• InChiKey: BKPKMSVWXHPGDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-bromo-7-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene 、 3-氯丙酰氯 以 硝基甲烷 为溶剂， 以76%的产率得到1-(7-bromo-4-methoxy-2,2-dimethyl-2,3-dihydro-1H-inden-5-yl)-3-chloropropan-1-one
  参考文献：
  名称：

  Illudalic acid as a potential LAR inhibitor: Synthesis, SAR, and preliminary studies on the mechanism of action

  摘要：

  A novel synthesis of the human leukocyte common antigen-related (LAR) phosphatase inhibitor, illudalic acid, has been achieved by a route more amenable to structure modi. cations. A series of simpler analogues of illudalic acid was synthesized and evaluated for potency in inhibiting LAR. The structure -activity relationship (SAR) study has shown that the 5-formyl group and the hemi-acetal lactone are crucial for effective inhibition of LAR activity, and are the key pharmacophores of illudalic acid. The fused dimethylcyclopentene ring moiety evidently helps to enhance the potency of illudalic acid against LAR. A preliminary study of the mechanism of action of illudalic acid against LAR was conducted using electrospray ionization mass spectrometry (ESI-MS) and molecular docking techniques. The results are in full agreement with the described mechanism. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.06.014
• 作为产物：
  描述：

  4-bromo-7-methoxy-2,2-dimethyl-2,3-dihydroinden-1-one 在 盐酸 、 amalgamated zinc 作用下， 以 乙醇 为溶剂， 以84%的产率得到4-bromo-7-methoxy-2,2-dimethyl-2,3-dihydro-1H-indene
  参考文献：
  名称：

  Illudalic acid as a potential LAR inhibitor: Synthesis, SAR, and preliminary studies on the mechanism of action

  摘要：

  A novel synthesis of the human leukocyte common antigen-related (LAR) phosphatase inhibitor, illudalic acid, has been achieved by a route more amenable to structure modi. cations. A series of simpler analogues of illudalic acid was synthesized and evaluated for potency in inhibiting LAR. The structure -activity relationship (SAR) study has shown that the 5-formyl group and the hemi-acetal lactone are crucial for effective inhibition of LAR activity, and are the key pharmacophores of illudalic acid. The fused dimethylcyclopentene ring moiety evidently helps to enhance the potency of illudalic acid against LAR. A preliminary study of the mechanism of action of illudalic acid against LAR was conducted using electrospray ionization mass spectrometry (ESI-MS) and molecular docking techniques. The results are in full agreement with the described mechanism. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.06.014