7,8-dimethoxy-3-methylisochroman-4-one | 945619-76-1

• 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: 7,8-dimethoxy-3-methylisochroman-4-one
• 英文别名: 7,8-dimethoxy-3-methyl-1H-isochromen-4-one
• CAS: 945619-76-1
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: YFYYVHCMMOFYJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  16
• 可旋转键数：
  2
• 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：

  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
• 作为产物：
  描述：

  6-bromo-2,3-dimethoxybenzaldehyde 在 sodium tetrahydroborate 、 叔丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.69h， 生成 7,8-dimethoxy-3-methylisochroman-4-one
  参考文献：
  名称：

  经由与Weinreb酰胺帕海姆型环化的4-异色满酮类的高效合成

  摘要：

  4-异色满酮类经由帕海姆型环化的Weinreb合成酰胺作为内部电子基团，吨正丁基锂作为被描述的锂试剂。该反应是有效的，并且可以在一分钟内完成。这个新的协议的应用范围进行了研究和所需产物可以以良好地获得优异的产率。此外，该方法的合成潜力还通过天然产物（±）-XJP的合成得到了进一步证明，该合成是通过六个步骤获得的，总收率高达54％。

  DOI：

  10.1016/j.tet.2015.08.028

文献信息

• Total synthesis and antihypertensive activity of (±)7,8-dihydroxy-3-methyl-isochromanone-4
  作者：Jie Liu、Hao Ren、Jinyi Xu、Renren Bai、Qi Yan、Wenlong Huang、Xiaoming Wu、Jihua Fu、Qiujuan Wang、Qian Wu、Rong Fu

  DOI：10.1016/j.bmcl.2008.12.102

  日期：2009.3

  This letter describes the total synthesis, preliminary biological evaluation and mechanism studies of a novel and structurally unique isochromanone, (±)7,8-dihydroxy-3-methyl-isochromanone-4 (1), a nature product contained in banana (Musa sapientum L.) peel. The bioassay showed that compound 1 displays potent antihypertensive activity in renal hypertensive rats and further mechanism studies revealed

  此信介绍的全合成，一种新型的初步生物评价和机制的研究和结构独特的异色满酮，（±）7,8-二羟基-3-甲基-异色满-4-（1），一个自然产物含在香蕉（芭蕉L.）剥皮。生物测定表明，化合物1在肾性高血压大鼠中显示出有效的降压活性，进一步的机理研究表明，它是一种ACEI抑制剂。
• Novel hybrids of natural isochroman-4-one bearing N-substituted isopropanolamine as potential antihypertensive candidates
  作者：Renren Bai、Xiaojing Huang、Xue Yang、Wen Hong、Yiqun Tang、Hequan Yao、Jieyun Jiang、Jie Liu、Mingqin Shen、Xiaoming Wu、Jinyi Xu

  DOI：10.1016/j.bmc.2013.02.044

  日期：2013.5

  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.
• An efficient synthesis of 4-isochromanones via Parham-type cyclization with Weinreb amide
  作者：Chaolei Wang、Zheng Wu、Jia Wang、Jie Liu、Hequan Yao、Aijun Lin、Jinyi Xu

  DOI：10.1016/j.tet.2015.08.028

  日期：2015.10

  The synthesis of 4-isochromanones via Parham-type cyclization with Weinreb amide as the internal electrophilic group, t-BuLi as the lithium reagent was described. The reaction was efficient and could be completed in one minute. The application scope of this new protocol was investigated and the desired products could be obtained in good to excellent yields. Besides, the synthetic potential of this

  4-异色满酮类经由帕海姆型环化的Weinreb合成酰胺作为内部电子基团，吨正丁基锂作为被描述的锂试剂。该反应是有效的，并且可以在一分钟内完成。这个新的协议的应用范围进行了研究和所需产物可以以良好地获得优异的产率。此外，该方法的合成潜力还通过天然产物（±）-XJP的合成得到了进一步证明，该合成是通过六个步骤获得的，总收率高达54％。