4,5,6,7-四氢-1-苯并呋喃-7-醇 | 110830-58-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 中文名称: 4,5,6,7-四氢-1-苯并呋喃-7-醇
• 英文名称: 4,5,6,7-tetrahydro-1-benzofuran-7-ol
• 英文别名: 4,5,6,7-tetrahydrobenzofuran-7-ol
• CAS: 110830-58-5
• 化学式: C₈H₁₀O₂
• 分子量: 138.166
• InChiKey: GLLCXMZXJQTQMQ-UHFFFAOYSA-N

物化性质

• 沸点：
  252.4±25.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  33.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,5,6,7-四氢-1-苯并呋喃-7-醇 在 palladium on activated charcoal 叠氮磷酸二苯酯 、 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 2.0h， 生成 4,5,6,7-tetrahydrobenzofuran-7-ylamine
  参考文献：
  名称：

  Enzymatic Resolution of Bicyclic 1-Heteroarylamines Using Candida antarctica Lipase B

  摘要：

  Candida antarctica lipase B has been used to kinetically resolve a structurally diverse series of bicyclic 1-heteroaryl primary amines by enantioselective acetylation. High yields of either enantiomer could be obtained with excellent enantioselectivity (90-99% ee), while the undesired enantiomer could, in some cases be recycled by thermal racemization. The absolute stereochemistry of the products was confirmed by an X-ray crystal structure.

  DOI：

  10.1021/jo026701r
• 作为产物：
  描述：

  4-(3-furyl)butanal 在 silver trifluoromethanesulfonate 、 (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以85%的产率得到4,5,6,7-四氢-1-苯并呋喃-7-醇
  参考文献：
  名称：

  Furan Approach to Vitamin D Analogues. Synthesis of the A-Ring of Calcitriol and 1α-Hydroxy-3-deoxyvitamin D₃

  摘要：

  The A-rings of calcitriol (1 alpha,25-dihydeoxyvitamin D-3) and 1 alpha-hydroxy-3-deoxyvitamin D-3 were synthesized using the furan approach The critical steps in the synthesis of the A-ring of calcitriol involved an asymmetric carbonyl-ene reaction of 3-methylene-2,3-dihydrofuran with 3-(tert-butyldimethylsiloxy)-propanal. a diostereoselective Friedel-Crafts hydroxyalkylation an oxidation of the 2.3-disubstituted furan to give a gamma-hydroxybutenolide and a Peterson olefinatiion The A-ring (Z)-dienol of calcitriol was synthesized in 12 steps from 3-(tert-butyldimethylsiloxy)propanal in 17% yield

  DOI：

  10.1021/jo101155c

文献信息

• Site- and Stereoselectivity in the Photochemical Oxetane Formation Reaction (Paternò–Büchi Reaction) of Tetrahydrobenzofuranols with Benzophenone: Hydroxy-directed Diastereoselectivity?
  作者：Youhei Yabuno、Yoshikazu Hiraga、Manabu Abe

  DOI：10.1246/cl.2008.822

  日期：2008.8.5

  The Paterno-Buchi reactions of tetrahydrobenzofuranols with benzophenone were investigated to reveal site- and stereoselectivity in oxetane formation reactions. Both selectivities were found to be largely dependent on the reaction temperature. The trans selectivity increased with a decrease in temperature, and the more-substituted oxetanes were selectively formed at high temperature.

  研究了四氢苯并呋喃醇与二苯甲酮的 Paterno-Buchi 反应，以揭示氧杂环丁烷形成反应中的位点和立体选择性。发现两种选择性在很大程度上取决于反应温度。反式选择性随着温度的降低而增加，并且在高温下选择性地形成更多取代的氧杂环丁烷。
• Total synthesis of (±)-furoscrobiculin B
  作者：Maki Seki、Toshihiro Sakamoto、Hiroshi Suemune、Ken Kanematsu

  DOI：10.1039/a607164c

  日期：——

  Total synthesis of (±)-furoscrobiculin B, a lactarane sesquiterpene isolated from basidiomycetes of mushrooms, has been achieved via an improved synthetic route of our previous work based on a Furan Ring Transfer (FRT) reaction and base-catalysed pinacol-type rearrangement.

  成功实现了从蘑菇担子菌中分离得到的乳菇烷倍半萜(±)-furoscrobiculin B的全合成，该合成路线基于我们之前工作的改进，利用呋喃环转移(FRT)反应和碱催化的片呐醇型重排反应进行。
• Synthetic Models Related to Methoxalen and Menthofuran–Cytochrome P450 (CYP) 2A6 Interactions. Benzofuran and Coumarin Derivatives as Potent and Selective Inhibitors of CYP2A6
  作者：Yuki Yamaguchi、Ichie Akimoto、Kyoko Motegi、Teruki Yoshimura、Keiji Wada、Naozumi Nishizono、Kazuaki Oda

  DOI：10.1248/cpb.c12-00872

  日期：——

  Human microsomal cytochrome P450 (CYP) 2A6 contributes extensively to nicotine detoxication but also activates tobacco-specific procarcinogens to mutagenic products. We prepared a series of benzofuran and coumarin derivatives that have inhibitory effects on the activity of human CYP2A6. The reported compounds methoxalen and menthofuran had potent inhibitory effects on the activity of CYP2A6 with IC50 values of 0.47 µM and 1.27 µM, respectively. Synthetic benzofuran (4-methoxybenzofuran: IC50=2.20 µM) and coumarin (5-methoxycoumarin: IC50=0.13 µM and 6-methoxycoumarin: IC50=0.64 µM) derivatives, which have more selective effects than those of methoxalen and menthofuran, exhibited comparable activities against CYP2A6. These compounds can be used as a lead compounds in the design of CYP2A6 inhibitor drugs to reduce smoking and tobacco-related cancers.

  人类微粒体细胞色素 P450 (CYP) 2A6 对尼古丁的解毒作用很大，但也能激活烟草特异性致癌物质，使其产生致突变产物。我们制备了一系列对人类 CYP2A6 活性有抑制作用的苯并呋喃和香豆素衍生物。已报道的化合物甲氧呋喃和薄荷呋喃对 CYP2A6 的活性有很强的抑制作用，其 IC50 值分别为 0.47 µM 和 1.27 µM 。合成苯并呋喃（4-甲氧基苯并呋喃：IC50=2.20 µM ）和香豆素（5-甲氧基香豆素：IC50=0.13 µM 和 6-甲氧基香豆素：IC50=0.64 µM) 衍生物对 CYP2A6 的活性相当，它们比甲氧沙林和薄荷呋喃的选择性更强。这些化合物可用作设计 CYP2A6 抑制剂药物的先导化合物，以减少吸烟和与烟草有关的癌症。
• Concentration and Temperature Dependency of Regio- and Stereoselectivity in a Photochemical [2 + 2] Cycloaddition Reaction (the Paternò−Büchi Reaction): Origin of the Hydroxy-Group Directivity
  作者：Youhei Yabuno、Yoshikazu Hiraga、Ryukichi Takagi、Manabu Abe

  DOI：10.1021/ja1088524

  日期：2011.3.2

  formation reactions, i.e., the Paternò-Büchi (PB) reactions, of tetrahydrobenzofuranol derivatives 1a-d with benzophenone (BP) was investigated to examine poorly understood hydroxy-group directivity on regio- and stereoselectivity. The selectivities of the PB reactions for allylic alcohols 1a,d were found to be largely dependent upon the concentration of the allylic alcohols and the reaction temperature

  研究了四氢苯并呋喃醇衍生物 1a-d 与二苯甲酮 (BP) 的一组光化学氧杂环丁烷形成反应，即 Paternò-Büchi (PB) 反应，以检查对区域和立体选择性知之甚少的羟基方向性。发现 PB 反应对烯丙醇 1a、d 的选择性很大程度上取决于烯丙醇的浓度和反应温度。在高浓度烯丙醇下区域选择性的温度依赖性变化类似于羟基保护的甲基醚 1b 和四氢苯并呋喃 (1c)。浓度对区域选择性的影响可以通过氢键聚集体来解释，它模拟了在 1b、c 的 PB 反应期间观察到的选择性。发现在低浓度 1a,d 下形成的高取代氧杂环丁烷 3a,d 的羟基定向顺式选择性大于在较高浓度 1a,d 时的选择性。发现 3a,d 的顺式选择性高于低取代氧杂环丁烷 2a,d。顺式配置的氧杂环丁烷的区域选择性高于反式配置的氧杂环丁烷。这些实验结果强烈表明，由氢键稳定诱导的羟基方向性在控制 PB 反应的区域选择性和立体选择性中
• Enzymatic Resolution of Bicyclic 1-Heteroarylamines Using <i>Candida antarctica</i> Lipase B
  作者：Krystyna A. Skupinska、Ernest J. McEachern、Ian R. Baird、Renato T. Skerlj、Gary J. Bridger

  DOI：10.1021/jo026701r

  日期：2003.5.1

  Candida antarctica lipase B has been used to kinetically resolve a structurally diverse series of bicyclic 1-heteroaryl primary amines by enantioselective acetylation. High yields of either enantiomer could be obtained with excellent enantioselectivity (90-99% ee), while the undesired enantiomer could, in some cases be recycled by thermal racemization. The absolute stereochemistry of the products was confirmed by an X-ray crystal structure.