6-ethyl-5,7-dimethoxy-3H-isobenzofuran-1-one | 203579-19-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: 6-ethyl-5,7-dimethoxy-3H-isobenzofuran-1-one
• 英文别名: 6-ethyl-5,7-dimethoxy-3H-2-benzofuran-1-one
• CAS: 203579-19-5
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: HCYDOGKGJCNRNH-UHFFFAOYSA-N

物化性质

• 沸点：
  418.8±45.0 °C(Predicted)
• 密度：
  1.189±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-ethyl-5,7-dimethoxy-3H-isobenzofuran-1-one 在 三溴化硼 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 72.0h， 生成 6-Ethyl-5-methoxy-7-(1-phenyl-1H-tetrazol-5-yloxy)-3H-isobenzofuran-1-one
  参考文献：
  名称：

  O-Methylasparvenone, a nitrogen-free serotonin antagonist

  摘要：

  O-Methylasparvenone (1) and asparvenone (2) were isolated from an Aspergillus parvulus Smith broth in a microbial screening for 5-HT2C ligands and found to be 5-HT2C antagonists. They represent the first nitrogen-free serotonin ligands. The absolute configuration of 1 was determined to be S by X-ray analysis of the corresponding Mosher-ester. A short and efficient synthesis of rac-1 was developed. This protocol was applied to the synthesis of derivatives of 1 and a structure-affinity relationship was established. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00160-0
• 作为产物：
  描述：

  4-ethyl-3,5-dimethoxybenzaldehyde 在 sodium tetrahydroborate 、 正丁基锂 、 四甲基乙二胺 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 6-ethyl-5,7-dimethoxy-3H-isobenzofuran-1-one
  参考文献：
  名称：

  O-Methylasparvenone, a nitrogen-free serotonin antagonist

  摘要：

  O-Methylasparvenone (1) and asparvenone (2) were isolated from an Aspergillus parvulus Smith broth in a microbial screening for 5-HT2C ligands and found to be 5-HT2C antagonists. They represent the first nitrogen-free serotonin ligands. The absolute configuration of 1 was determined to be S by X-ray analysis of the corresponding Mosher-ester. A short and efficient synthesis of rac-1 was developed. This protocol was applied to the synthesis of derivatives of 1 and a structure-affinity relationship was established. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00160-0

文献信息

• Syntheses of<i>O</i>-Methylasparvenone-Derived Serotonin-Receptor Antagonists
  作者：Michael Bös、Heinz Stadler、Jürgen Wichmann、François Jenck、James R. Martin、Jean-Luc Moreau、Andrew J. Sleight

  DOI：10.1002/hlca.19980810306

  日期：——

  Based on O-methylasparvenone (1), a N-free 5HT2C antagonist with moderate affinity (pKi = 6.7), derivatives bearing dimethylamino (7), (dimethylamino)methyl (17, 18, 21, and 22), and aminomethyl substituents (26) in place of the benzylic OH group of 1 as well as pyrrolidine- (33) and piperidine-fused derivatives (29, 43, and 45) were synthesized. In contrast to the lead structure 1, these new ligands

  基于ø -methylasparvenone（1），其N-自由5HT 2 ç拮抗剂与中等亲和力（对ķ我= 6.7），衍生物轴承二甲基氨基（7），（二甲基氨基）甲基（17，18，21，和22），和氨基甲基的取代基（26）代替苄基的OH基团中的1以及吡咯烷（33）和哌啶稠合衍生物（29，43，和45）的合成。与引线结构1相反这些新的配体在大鼠体内具有活性。三轮车33和45显示出对5HT 2 C受体的高亲和力（p K i = 8）。