苯并二氢吡喃-8-羰酰氯 | 1034566-09-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 苯并二氢吡喃-8-羰酰氯
• 英文名称: Chroman-8-carbonyl chloride
• 英文别名: 3,4-dihydro-2H-chromene-8-carbonyl chloride
• CAS: 1034566-09-0
• 化学式: C₁₀H₉ClO₂
• mdl: MFCD12198123
• 分子量: 196.633
• InChiKey: TTYLUAYKWAEQDM-UHFFFAOYSA-N

物化性质

• 沸点：
  319.6±31.0 °C(Predicted)
• 密度：
  1.279±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  苯并二氢吡喃-8-羰酰氯 在 氯磺酸 、 4-二甲氨基吡啶 、 sodium hydroxide 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 6.0h， 生成
  参考文献：
  名称：

  Synthesis and phosphodiesterase 5 inhibitory activity of novel phenyl ring modified sildenafil analogues

  摘要：

  New sildenafil analogues containing an ether ring fused into the phenyl moiety, 6a-d and 7a-d, were efficiently synthesized from the readily available starting materials, 1a-d and 2, in five steps. Ab initio calculations indicated that introduction of a cyclic ether to the phenyl group might enhance the co-planarity of the molecule. The torsional angles were calculated to be 2-3 degrees for the 5-membered cyclic ether derivatives, 6a, 6c, 7a, and 7c, and 12-16 degrees for the 6-membered ones, 6b, 6d, 7b, and 7d. On the other hand, sildenafil showed the least co-planarity with the torsional angle of 23 degrees compared with the target compounds, 6a-d and 7a-d. In the enzyme assay, however, the in Vitro PDE 5 inhibitory activity was found out to be inversely related to the degree of coplanarity. In other words, the least planar sildenafil showed the highest activity, and the most planar 5-membered cyclic ether derivatives were least active by 100-200-fold compared with sildenafil. Our study clearly demonstrated that the open chain 2'-alkoxy group of the phenyl ring, although less effective for inducing the co-planarity, seemed to act as a much better lipophilic requirement than the cyclic alkoxy moiety. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00055-4
• 作为产物：
  描述：

  苯并二氢吡喃-8-羧酸 在 氯化亚砜 作用下， 反应 3.0h， 生成 苯并二氢吡喃-8-羰酰氯
  参考文献：
  名称：

  Synthesis and phosphodiesterase 5 inhibitory activity of novel phenyl ring modified sildenafil analogues

  摘要：

  New sildenafil analogues containing an ether ring fused into the phenyl moiety, 6a-d and 7a-d, were efficiently synthesized from the readily available starting materials, 1a-d and 2, in five steps. Ab initio calculations indicated that introduction of a cyclic ether to the phenyl group might enhance the co-planarity of the molecule. The torsional angles were calculated to be 2-3 degrees for the 5-membered cyclic ether derivatives, 6a, 6c, 7a, and 7c, and 12-16 degrees for the 6-membered ones, 6b, 6d, 7b, and 7d. On the other hand, sildenafil showed the least co-planarity with the torsional angle of 23 degrees compared with the target compounds, 6a-d and 7a-d. In the enzyme assay, however, the in Vitro PDE 5 inhibitory activity was found out to be inversely related to the degree of coplanarity. In other words, the least planar sildenafil showed the highest activity, and the most planar 5-membered cyclic ether derivatives were least active by 100-200-fold compared with sildenafil. Our study clearly demonstrated that the open chain 2'-alkoxy group of the phenyl ring, although less effective for inducing the co-planarity, seemed to act as a much better lipophilic requirement than the cyclic alkoxy moiety. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00055-4

文献信息

• Synthesis and phosphodiesterase 5 inhibitory activity of novel phenyl ring modified sildenafil analogues
  作者：Dae-Kee Kim、Namkyu Lee、Ju Young Lee、Do Hyun Ryu、Jae-Sun Kim、Suk-Ho Lee、Jin-Young Choi、Kieyoung Chang、Young-Woo Kim、Guang-Jin Im、Won-Son Choi、Tae-Kon Kim、Je-Ho Ryu、Nam-Ho Kim、Kyoungrim Lee

  DOI：10.1016/s0968-0896(01)00055-4

  日期：2001.6

  New sildenafil analogues containing an ether ring fused into the phenyl moiety, 6a-d and 7a-d, were efficiently synthesized from the readily available starting materials, 1a-d and 2, in five steps. Ab initio calculations indicated that introduction of a cyclic ether to the phenyl group might enhance the co-planarity of the molecule. The torsional angles were calculated to be 2-3 degrees for the 5-membered cyclic ether derivatives, 6a, 6c, 7a, and 7c, and 12-16 degrees for the 6-membered ones, 6b, 6d, 7b, and 7d. On the other hand, sildenafil showed the least co-planarity with the torsional angle of 23 degrees compared with the target compounds, 6a-d and 7a-d. In the enzyme assay, however, the in Vitro PDE 5 inhibitory activity was found out to be inversely related to the degree of coplanarity. In other words, the least planar sildenafil showed the highest activity, and the most planar 5-membered cyclic ether derivatives were least active by 100-200-fold compared with sildenafil. Our study clearly demonstrated that the open chain 2'-alkoxy group of the phenyl ring, although less effective for inducing the co-planarity, seemed to act as a much better lipophilic requirement than the cyclic alkoxy moiety. (C) 2001 Elsevier Science Ltd. All rights reserved.