7-methoxy-3-methyl-8-(oxiran-2-ylmethoxy)isochroman-4-one | 1262143-00-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 7-methoxy-3-methyl-8-(oxiran-2-ylmethoxy)isochroman-4-one
• CAS: 1262143-00-9
• 化学式: C₁₄H₁₆O₅
• 分子量: 264.278
• InChiKey: UKVJTCLYMWPDKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.57
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  57.29
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  7-methoxy-3-methyl-8-(oxiran-2-ylmethoxy)isochroman-4-one 、 二甲胺 以 甲醇 为溶剂， 以76%的产率得到8-(3-dimethylamino-2-hydroxypropoxy)-7-methoxy-3-methylisochroman-4-one
  参考文献：
  名称：

  Novel hybrids of natural isochroman-4-one bearing N-substituted isopropanolamine as potential antihypertensive candidates

  摘要：

  A series of novel hybrids of natural isochroman-4-one bearing isopropanolamine moiety were designed, synthesized and evaluated for their antihypertensive activity. It was found that compound IIId, prepared by hybridizing N-isopropyl substituted isopropanolamine functionality to a phenolic oxygen of isochroman-4-one, exhibited potent beta(1)-adrenoceptor blocking effect comparable to the well-known antihypertensive drug propranolol. Additionally, IIId significantly reduced the systolic and diastolic blood pressure in SHRs by over 40%, which was obviously stronger than the lead compounds 7,8-dihydroxy-3-methyl-isochroman-4-one (XJP) and its analogue XJP-B. Overall, IIId may be a promising antihypertensive candidate for further investigation. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.02.044
• 作为产物：
  描述：

  7,8-dimethoxy-3-methylisochroman-4-one 在 aluminum (III) chloride 、 potassium carbonate 、 sodium iodide 作用下， 以 氯仿 、 丙酮 为溶剂， 反应 3.5h， 生成 7-methoxy-3-methyl-8-(oxiran-2-ylmethoxy)isochroman-4-one
  参考文献：
  名称：

  Novel hybrids of natural isochroman-4-one bearing N-substituted isopropanolamine as potential antihypertensive candidates

  摘要：

  A series of novel hybrids of natural isochroman-4-one bearing isopropanolamine moiety were designed, synthesized and evaluated for their antihypertensive activity. It was found that compound IIId, prepared by hybridizing N-isopropyl substituted isopropanolamine functionality to a phenolic oxygen of isochroman-4-one, exhibited potent beta(1)-adrenoceptor blocking effect comparable to the well-known antihypertensive drug propranolol. Additionally, IIId significantly reduced the systolic and diastolic blood pressure in SHRs by over 40%, which was obviously stronger than the lead compounds 7,8-dihydroxy-3-methyl-isochroman-4-one (XJP) and its analogue XJP-B. Overall, IIId may be a promising antihypertensive candidate for further investigation. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.02.044