6,7,8,8a-tetrahydro-6-hydroxy-3,8a-dimethylnaphtho[2,3-b]furan-9(4H)-one | 503624-26-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: 6,7,8,8a-tetrahydro-6-hydroxy-3,8a-dimethylnaphtho[2,3-b]furan-9(4H)-one
• 英文别名: 6-Hydroxy-3,8a-dimethyl-4,6,7,8-tetrahydrobenzo[f][1]benzofuran-9-one
• CAS: 503624-26-8
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: GBAJEBUBKFWJPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  50.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6,7,8,8a-tetrahydro-6-hydroxy-3,8a-dimethylnaphtho[2,3-b]furan-9(4H)-one 在 platinum(IV) oxide lithium aluminium tetrahydride 、 氢气 、 sodium hydride 、 戴斯-马丁氧化剂 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 28.0h， 生成
  参考文献：
  名称：

  Regiospecific substitution of the carbon–boron bond of tris(4-trimethylsilylfuran-3-yl)boroxine and tris(4-methylfuran-3-yl)boroxine. Model approaches towards sesquiterpenoid furanoeudesmanes

  摘要：

  Furan-containing compounds occur abundantly in nature. Among them, the sesquiterpenoid furanoeudesmanes are particularly interesting due to their allergenic, plant-growth inhibiting, antibacterial as well as antitumor properties. Recently an organoboron protocol has been developed in our laboratory for the preparation of regiospecific-substituted furans. By utilizing such methodology, two common intermediates 1 and 2 that may lead to the synthesis of naturally occurring tubipofuran (3) furanoeudesm-4-ene (4) and furanoeudesma-1,4-dien-6-one (5) were obtained. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01519-3
• 作为产物：
  描述：

  ethyl 5-bromo-2-bromomethyl-1-methyl-4-oxocyclohex-2-ene-1-carboxylate 在 sodium hydroxide 、 sodium tetrahydroborate 、 potassium phosphate 、 四(三苯基膦)钯 、 cerium(III) chloride 、 对甲苯磺酸 、 溶剂黄146 、 三氟乙酸酐 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 苯 为溶剂， 反应 114.17h， 生成 6,7,8,8a-tetrahydro-6-hydroxy-3,8a-dimethylnaphtho[2,3-b]furan-9(4H)-one
  参考文献：
  名称：

  Regiospecific substitution of the carbon–boron bond of tris(4-trimethylsilylfuran-3-yl)boroxine and tris(4-methylfuran-3-yl)boroxine. Model approaches towards sesquiterpenoid furanoeudesmanes

  摘要：

  Furan-containing compounds occur abundantly in nature. Among them, the sesquiterpenoid furanoeudesmanes are particularly interesting due to their allergenic, plant-growth inhibiting, antibacterial as well as antitumor properties. Recently an organoboron protocol has been developed in our laboratory for the preparation of regiospecific-substituted furans. By utilizing such methodology, two common intermediates 1 and 2 that may lead to the synthesis of naturally occurring tubipofuran (3) furanoeudesm-4-ene (4) and furanoeudesma-1,4-dien-6-one (5) were obtained. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01519-3

文献信息

• Regiospecific substitution of the carbon–boron bond of tris(4-trimethylsilylfuran-3-yl)boroxine and tris(4-methylfuran-3-yl)boroxine. Model approaches towards sesquiterpenoid furanoeudesmanes
  作者：Chung-Yan Yick、Tsun-Keung Tsang、Henry N.C Wong

  DOI：10.1016/s0040-4020(02)01519-3

  日期：2003.1

  Furan-containing compounds occur abundantly in nature. Among them, the sesquiterpenoid furanoeudesmanes are particularly interesting due to their allergenic, plant-growth inhibiting, antibacterial as well as antitumor properties. Recently an organoboron protocol has been developed in our laboratory for the preparation of regiospecific-substituted furans. By utilizing such methodology, two common intermediates 1 and 2 that may lead to the synthesis of naturally occurring tubipofuran (3) furanoeudesm-4-ene (4) and furanoeudesma-1,4-dien-6-one (5) were obtained. (C) 2003 Elsevier Science Ltd. All rights reserved.