1-cyano-5-hydroxy-benzocyclobutene-1-carboxylic acid methyl ester | 1447139-64-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 1-cyano-5-hydroxy-benzocyclobutene-1-carboxylic acid methyl ester
• CAS: 1447139-64-1
• 化学式: C₁₁H₉NO₃
• 分子量: 203.197
• InChiKey: GPCRMZVSCGVZCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.88
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  70.32
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-cyano-5-hydroxy-benzocyclobutene-1-carboxylic acid methyl ester 在 咪唑 、 4-二甲氨基吡啶 、 锂硼氢 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 4-tert-Butyldimethylsiloxy-1-cyano-1-hydroxymethylbenzocyclobutene
  参考文献：
  名称：

  Structure–activity-relationship studies on dihydrofuran-fused perhydrophenanthrenes as an anti-Alzheimer’s disease agent

  摘要：

  As an extended study on development of anti-Alzheimer's disease agent, we newly synthesized various dihydrofuran-fused perhydrophenanthrenes via o-quinodimethane chemistry. This study revealed that the introduction of carbon side-chain on 8-position or removal of the acetal moiety on 3-position arose a cytotoxicity on rat cortical neurons. On the other hand, the ethereal or thio-ethereal substituent on 8-position enhanced the elongation effect on A beta-damaged neurons. The necessity of the cyano group on 10b position was also proved in this structure-activity-relationship study. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.059
• 作为产物：
  描述：

  4-羟基双环[4.2.0]辛-1,3,5-三烯-7-甲腈 、 氰基甲酸甲酯 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.5h， 以73%的产率得到1-cyano-5-hydroxy-benzocyclobutene-1-carboxylic acid methyl ester
  参考文献：
  名称：

  Structure–activity-relationship studies on dihydrofuran-fused perhydrophenanthrenes as an anti-Alzheimer’s disease agent

  摘要：

  As an extended study on development of anti-Alzheimer's disease agent, we newly synthesized various dihydrofuran-fused perhydrophenanthrenes via o-quinodimethane chemistry. This study revealed that the introduction of carbon side-chain on 8-position or removal of the acetal moiety on 3-position arose a cytotoxicity on rat cortical neurons. On the other hand, the ethereal or thio-ethereal substituent on 8-position enhanced the elongation effect on A beta-damaged neurons. The necessity of the cyano group on 10b position was also proved in this structure-activity-relationship study. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.059