cis-4-phenylcyclohexene-4,5-dicarboxylic acid anhydride | 64504-91-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异苯并呋喃
• 英文名称: cis-4-phenylcyclohexene-4,5-dicarboxylic acid anhydride
• 英文别名: (3AS,7AR)-3A-Phenyl-3A,4,7,7A-tetrahydro-2-benzofuran-1,3-dione；(3aR,7aS)-7a-phenyl-4,7-dihydro-3aH-2-benzofuran-1,3-dione
• CAS: 64504-91-2；87923-79-3
• 化学式: C₁₄H₁₂O₃
• 分子量: 228.247
• InChiKey: OFWIZCWHBRZEKV-SMDDNHRTSA-N

物化性质

• 沸点：
  388.8±42.0 °C(Predicted)
• 密度：
  1.289±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cis-4-phenylcyclohexene-4,5-dicarboxylic acid anhydride 在 lithium aluminium tetrahydride 、 氢气 作用下， 生成 (3aR,7aS)-2-methyl-7a-phenyl-3,3a,4,5,6,7-hexahydro-1H-isoindole
  参考文献：
  名称：

  Synthesis and Pharmacological Characterization of Bicyclic Triple Reuptake Inhibitor 3-Aryl Octahydrocyclopenta[c]pyrrole Analogues

  摘要：

  The present work expands the chemical space known to offer potent inhibition of the serotonin transporter (SERT), norepinephrine transporter (NET), and dopamine transporter (DAT) and discloses novel bicyclic octahydrocyclopenta[c]pyrrole and octahydro-1H-isoindole scaffolds as potent triple reuptake inhibitors (TRIs) for the potential treatment of depression. Optimized compounds 22a (SEAT, NET, DAT, IC(50) = 20, 109, 430 nM), 23a (SERT, NET, DAT, IC(50) = 29, 85, 168 nM), and 26a (SERT, NET, DAT, IC(50) = 53, 150, 140 nM) were highly brain penetrant, active in vivo in the mouse tail suspension test at 10 and 30 mpk PO, and were not generally motor stimulants at doses ranging from 1 to 30 mpk PO. Moderate in vitro cytochrome P450 (CYP) and potassium ion channel Kv11.1 (hERG) inhibition were uncovered as potential liabilities for the chemical series.

  DOI：

  10.1021/jm101312a
• 作为产物：
  描述：

  苯基丁二酸 在 selenium(IV) oxide 、 对苯二酚 作用下， 以 1,4-二氧六环 、 乙酸酐 为溶剂， 反应 36.0h， 生成 cis-4-phenylcyclohexene-4,5-dicarboxylic acid anhydride
  参考文献：
  名称：

  Bond fixation in annulenes. 16. Synthesis of the 1,2-dimethyl-3-phenylcyclooctatetraene .dblarw. 1,8-dimethyl-2-phenylcyclooctatetraene bond shift isomer pair. Probe of the relative size of a flanking phenyl substituent by means of racemization kinetics

  摘要：

  DOI：

  10.1021/ja00364a031