5-hydroxy-2-methoxy-2-methyl-2,3-dihydrobenzofuran-4-carbaldehyde | 1072895-55-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: 5-hydroxy-2-methoxy-2-methyl-2,3-dihydrobenzofuran-4-carbaldehyde
• 英文别名: 5-hydroxy-2-methoxy-2-methyl-3H-1-benzofuran-4-carbaldehyde
• CAS: 1072895-55-6
• 化学式: C₁₁H₁₂O₄
• 分子量: 208.214
• InChiKey: RIPYNNUASMCKTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-hydroxy-2-methoxy-2-methyl-2,3-dihydrobenzofuran-4-carbaldehyde 、 异丁烯 在 ytterbium(III) triflate 、 原甲酸三甲酯 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 61.0h， 以56%的产率得到2,7,7-trimethyl-7H-furo[3,2-f]chromene
  参考文献：
  名称：

  A new synthetic access to furo[3,2-f]chromene analogues of an antimycobacterial

  摘要：

  From the structure of 3,3-dimethyl-3H-benzofuro[3,2-f][1]-benzopyran, a selective in vitro inhibitor of mycobacterial growth, we have undertaken a structure-activity relationship investigation. We wish to report here our results on the use of [2+3] cycloadditions between 2-formylbenzoquinone and various enol derivatives to give various 4-formyl-5-hydroxy benzofurans. In the next step, an ytterbium triflate-catalysed reaction with 2-methylpropene allowed the preparation of various original furo[3,2-f]chromenes derivatives. Their biological evaluation on the growth of Mycobacterium smegmatis as well as Mycobacterium tuberculosis pointed out that some analogues were four times more active than the initial hit. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.06.057
• 作为产物：
  描述：

  2,5-二羟基苯甲醛 、 2-甲氧基丙烯 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙酸乙酯 为溶剂， 反应 1.5h， 以68%的产率得到5-hydroxy-2-methoxy-2-methyl-2,3-dihydrobenzofuran-4-carbaldehyde
  参考文献：
  名称：

  A new synthetic access to furo[3,2-f]chromene analogues of an antimycobacterial

  摘要：

  From the structure of 3,3-dimethyl-3H-benzofuro[3,2-f][1]-benzopyran, a selective in vitro inhibitor of mycobacterial growth, we have undertaken a structure-activity relationship investigation. We wish to report here our results on the use of [2+3] cycloadditions between 2-formylbenzoquinone and various enol derivatives to give various 4-formyl-5-hydroxy benzofurans. In the next step, an ytterbium triflate-catalysed reaction with 2-methylpropene allowed the preparation of various original furo[3,2-f]chromenes derivatives. Their biological evaluation on the growth of Mycobacterium smegmatis as well as Mycobacterium tuberculosis pointed out that some analogues were four times more active than the initial hit. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.06.057