6-methoxy-2,2-dimethyl-3,4-dihydro-2H-naphtho[1,2-b]pyran-3-ol | 645413-83-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 6-methoxy-2,2-dimethyl-3,4-dihydro-2H-naphtho[1,2-b]pyran-3-ol
• 英文别名: 6-Methoxy-2,2-dimethyl-3,4-dihydrobenzo[h]chromen-3-ol；6-methoxy-2,2-dimethyl-3,4-dihydrobenzo[h]chromen-3-ol
• CAS: 645413-83-8
• 化学式: C₁₆H₁₈O₃
• 分子量: 258.317
• InChiKey: DMGORVXGDQSYNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-methoxy-2,2-dimethyl-3,4-dihydro-2H-naphtho[1,2-b]pyran-3-ol 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以95%的产率得到5-bromo-6-methoxy-2,2-dimethyl-3,4-dihydro-2H-naphtho[1,2-b]pyran-3-ol
  参考文献：
  名称：

  Synthesis of mollugin

  摘要：

  The total synthesis of mollugin, a major constituent of rubiaceous herbs, using a straightforward synthetic approach starting from 1,4-naphthoquinone via a sequence of reactions, including selective prenylation, epoxidation, reduction of the quinone moiety, acid-catalysed ring expansion, bromination, dehydration and methoxycarbonylation is presented. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.014
• 作为产物：
  描述：

  2-(2,3-epoxy-3-methylbutyl)-1,4-naphthoquinone 在 sodium dithionite 、 potassium carbonate 作用下， 以 乙醚 、 水 、 丙酮 为溶剂， 反应 9.5h， 生成 6-methoxy-2,2-dimethyl-3,4-dihydro-2H-naphtho[1,2-b]pyran-3-ol
  参考文献：
  名称：

  Synthesis of mollugin

  摘要：

  The total synthesis of mollugin, a major constituent of rubiaceous herbs, using a straightforward synthetic approach starting from 1,4-naphthoquinone via a sequence of reactions, including selective prenylation, epoxidation, reduction of the quinone moiety, acid-catalysed ring expansion, bromination, dehydration and methoxycarbonylation is presented. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.014

文献信息

• Synthesis of mollugin
  作者：Sven Claessens、Bart Kesteleyn、Tuyen Nguyen Van、Norbert De Kimpe

  DOI：10.1016/j.tet.2006.06.014

  日期：2006.8

  The total synthesis of mollugin, a major constituent of rubiaceous herbs, using a straightforward synthetic approach starting from 1,4-naphthoquinone via a sequence of reactions, including selective prenylation, epoxidation, reduction of the quinone moiety, acid-catalysed ring expansion, bromination, dehydration and methoxycarbonylation is presented. (c) 2006 Elsevier Ltd. All rights reserved.