2-<4-(7-methoxy-2-methylbenzofuranyl)>-6,7-(methylenedioxy)-1-naphthol | 149526-45-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-<4-(7-methoxy-2-methylbenzofuranyl)>-6,7-(methylenedioxy)-1-naphthol
• 英文别名: 2-(7-methoxy-2-methylbenzofuran-4-yl)-6,7-methylenedioxy-1-naphthol；6-(7-Methoxy-2-methyl-1-benzofuran-4-yl)benzo[f][1,3]benzodioxol-5-ol
• CAS: 149526-45-4
• 化学式: C₂₁H₁₆O₅
• 分子量: 348.355
• InChiKey: DZAGIJLXKIQYAK-UHFFFAOYSA-N

物化性质

• 沸点：
  535.9±50.0 °C(Predicted)
• 密度：
  1.362±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  61.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-<4-(7-methoxy-2-methylbenzofuranyl)>-6,7-(methylenedioxy)-1-naphthol 在 palladium on activated charcoal 二甲基硫 、 氢气 、 potassium carbonate 、 臭氧 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， -70.0~60.0 ℃ 、101.33 kPa 条件下， 反应 7.93h， 生成 17,18-Dimethoxy-5,7,21-trioxapentacyclo[11.8.0.02,10.04,8.014,19]henicosa-1(13),2,4(8),9,11,14(19),15,17-octaen-20-ol
  参考文献：
  名称：

  Structure and synthesis of arnottin I: a 6H-benzo[d]naphtho[1, 2-b]pyran-6-one derivative from a plant source

  摘要：

  Arnottin I 2 isolated from Xanthoxylum arnottianum Maxim and of previously unknown structure has been unambiguously synthesized utilizing a 2-methylarenofuran as a masked salicylaldehyde. This is the first occurrence of a 6H-benzo[d]naphtho[1,2-b]pyran-6-one derivative, the same skeleton as that of gilvocarsin-type antibiotics showing antitumour activity, from a plant source.

  DOI：

  10.1039/p19930001019
• 作为产物：
  描述：

  2-<4-(7-methoxy-2-methylbenzofuranyl)>-6,7-methylenedioxy-3,4-dihydronaphthalen-1(2H)-one 在 2-甲基丁-1,3-二烯-1-醇乙酸酯 、 对甲苯磺酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 生成 2-<4-(7-methoxy-2-methylbenzofuranyl)>-6,7-(methylenedioxy)-1-naphthol
  参考文献：
  名称：

  Structure and synthesis of arnottin I: a 6H-benzo[d]naphtho[1, 2-b]pyran-6-one derivative from a plant source

  摘要：

  Arnottin I 2 isolated from Xanthoxylum arnottianum Maxim and of previously unknown structure has been unambiguously synthesized utilizing a 2-methylarenofuran as a masked salicylaldehyde. This is the first occurrence of a 6H-benzo[d]naphtho[1,2-b]pyran-6-one derivative, the same skeleton as that of gilvocarsin-type antibiotics showing antitumour activity, from a plant source.

  DOI：

  10.1039/p19930001019

文献信息

• Nitrosation of Phenolic Substrates under Mildly Basic Conditions:  Selective Preparation of <i>p</i>-Quinone Monooximes and Their Antiviral Activities
  作者：Tsutomu Ishikawa、Toshiko Watanabe、Hisashi Tanigawa、Tatsuru Saito、Ken-Ichiro Kotake、Yoshiaki Ohashi、Hisashi Ishii

  DOI：10.1021/jo951873s

  日期：1996.1.1

  Nitrosation of 3-methoxyphenol and 1-naphthol were examined under both acidic (NaNO(2)-EtCO(2)H-H(2)O) and basic (i-AmNO(2)-K(2)CO(3)-DMF) conditions. Acidic nitrosations afforded ortho-directed products, whereas para-directed nitrosations were observed under basic conditions to yield p-quinone monooximes. The basic para-directed nitrosation was further examined using 15 phenols, two naphthols, and

  在酸性（NaNO（2）-EtCO（2）HH（2）O）和碱性（i-AmNO（2）-K（2）CO（3）-DMF下都检查了3-甲氧基苯酚和1-萘酚的亚硝化） 条件。酸性亚硝化提供了邻位定向的产物，而在碱性条件下观察到对位亚硝化可生成对醌单肟。使用15个酚，两个萘酚和四个酚杂环进一步检查了基本的对位亚硝化反应。一锅操作进行基本亚硝化，然后用硫酸二甲酯进行甲基化，可以高收率得到相应的甲基醚。衍生自3-甲氧基苯酚和8-羟基喹啉的两种对醌单肟对HSV-1具有中等活性，后一种肟对HSV-2也有效。另一方面，对苯二酚单肟衍生自水杨酸甲酯，1-萘酚，
• Air Oxidation of 2-Aryl-1-tetralones in Basic, Neutral, and Acidic Media:  An Unprecedented Oxidative Aryl Migration to 2-Aryloxy-1-naphthols under Acidic Condition
  作者：Tsutomu Ishikawa、Keiko Hino、Takaaki Yoneda、Masayuki Murota、Kentaro Yamaguchi、Toshiko Watanabe

  DOI：10.1021/jo9824854

  日期：1999.7.1
• Structure and synthesis of arnottin I: a 6H-benzo[d]naphtho[1, 2-b]pyran-6-one derivative from a plant source
  作者：Hisashi Ishii、Tsutomu Ishikawa、Masayuki Murota、Yoshiyuki Aoki、Takashi Harayama

  DOI：10.1039/p19930001019

  日期：——

  Arnottin I 2 isolated from Xanthoxylum arnottianum Maxim and of previously unknown structure has been unambiguously synthesized utilizing a 2-methylarenofuran as a masked salicylaldehyde. This is the first occurrence of a 6H-benzo[d]naphtho[1,2-b]pyran-6-one derivative, the same skeleton as that of gilvocarsin-type antibiotics showing antitumour activity, from a plant source.