4-羟基双环[4.2.0]辛-1,3,5-三烯-7-甲腈 | 242473-47-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 4-羟基双环[4.2.0]辛-1,3,5-三烯-7-甲腈
• 英文名称: 5-hydroxybenzocyclobutene-1-carbonitrile
• 英文别名: 1-cyano-5-hydroxybenzocyclobutane；4-Hydroxybicyclo[4.2.0]octa-1,3,5-triene-7-carbonitrile；4-hydroxybicyclo[4.2.0]octa-1(6),2,4-triene-7-carbonitrile
• CAS: 242473-47-8
• 化学式: C₉H₇NO
• 分子量: 145.161
• InChiKey: IUSMYJIUZKNWLE-UHFFFAOYSA-N

物化性质

• 沸点：
  358.9±42.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-羟基双环[4.2.0]辛-1,3,5-三烯-7-甲腈 在 正丁基锂 、 四丙基高钌酸铵 、 三氟甲磺酸三甲基硅酯 、 4-甲基苯磺酸吡啶 、 N-甲基吗啉氧化物 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 7.59h， 生成 1-[3-(furan-3-yl)-3-oxoprop-1-yl]-5-(triisopropylsilyloxy)benzocyclobutene-1-carbonitrile ethylene ketal
  参考文献：
  名称：

  Synthesis and biological evaluation of dihydrofuran-fused perhydrophenanthrenes as a new anti-influenza agent having novel structural characteristic

  摘要：

  Dihydrofuran-fused perhydrophenanthrenes were synthesized by means of o-quinodimethane chemistry with high generality and stereoselectivity, and found to exhibit potent anti-influenza activity. These compounds exerted an inhibitory effect on various strains of influenza virus growth, including influenza A and B, with a concentration dependent manner, and direct cytotoxicity was low. Several biological experiments suggested that these new drugs affected a virus replication process before mRNA synthesis stage. Novel rigid cage-type of structural characteristic of the compounds has not been found in hitherto anti-influenza drugs, and will provide new basis and motif for exploring promising and unprecedented anti-influenza agents. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.09.046
• 作为产物：
  描述：

  1-cyano-5-methoxybenzocyclobutane 在 碘代三甲硅烷 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以86%的产率得到4-羟基双环[4.2.0]辛-1,3,5-三烯-7-甲腈
  参考文献：
  名称：

  Synthesis and biological evaluation of dihydrofuran-fused perhydrophenanthrenes as a new anti-influenza agent having novel structural characteristic

  摘要：

  Dihydrofuran-fused perhydrophenanthrenes were synthesized by means of o-quinodimethane chemistry with high generality and stereoselectivity, and found to exhibit potent anti-influenza activity. These compounds exerted an inhibitory effect on various strains of influenza virus growth, including influenza A and B, with a concentration dependent manner, and direct cytotoxicity was low. Several biological experiments suggested that these new drugs affected a virus replication process before mRNA synthesis stage. Novel rigid cage-type of structural characteristic of the compounds has not been found in hitherto anti-influenza drugs, and will provide new basis and motif for exploring promising and unprecedented anti-influenza agents. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.09.046

文献信息

• Heterocycloalkylbenzocyclobutane and heteroarylbenzocyclobutane compounds
  申请人：——

  公开号：US20020019380A1

  公开（公告）日：2002-02-14

  A compound selected from those of formula (I): 1 wherein: overscore (_____)} denotes single bond or double bond, n is integer from 1 to 6 inclusive, R 1 , and R 2 represent a group selected from hydrogen, linear or branched (C 1 -C 6 )-alkyl, aryl, arylalkyl, cycloalkyl, cycloalkylalkyl, alkenyl, alkynyl, heterocycloalkyl, heterocycloalkylalkyl, heteroaryl, and heteroarylalkyl, X represents a group selected from —CH═CH—, oxygen, S(O) m wherein m is integer from 0 to 2 inclusive, and NR 3 wherein R 3 represents a group as defined in the description, Y represents CH or CH 2 depending on whether _____ denotes single bond or double bond, or may have the additional meaning of oxygen when X represents oxygen, T represents monocyclic or polycyclic (C 3 -C 10 )cycloalkyl optionally containing within the ring system oxygen, selenium, S(O) p , NR 3 , or SiR 4 R 5 wherein p, R 3 , R 4 , and R 5 are as defined in the description, its isomers and addition salts thereof with a pharmaceutically-acceptable acid or base, and medicinal products containing the same are useful in the treatment of CNS disorders.

  从以下通式（I）的化合物中选择的一种化合物：1其中：overscore (_____)}表示单键或双键，n是1至6（含）的整数，R1和R2表示从氢、直链或支链（C1-C6）-烷基、芳基、芳基烷基、环烷基、环烷基烷基、烯基、炔基、杂环烷基、杂环烷基烷基、杂芳基和杂芳基烷基中选择的基团，X表示从—CH═CH—、氧、S(O)m（其中m是0至2（含）的整数）和NR3（其中R3表示如说明书中定义的基团）中选择的基团，Y表示CH或CH2取决于_____表示单键或双键，或者当X表示氧时，Y还可以有氧的含义，T表示含或不含环系统内氧、硒、S(O)p、NR3或SiR4R5的单环或多环（C3-C10）环烷基（其中p、R3、R4和R5如说明书中定义），其异构体和与药学上可接受的酸或碱形成的加成盐，以及含有这些化合物的药物制剂，可用于治疗中枢神经系统疾病。
• Benzocyclobutane compounds
  申请人：Adir et Compagnie

  公开号：US06107345A1

  公开（公告）日：2000-08-22

  A compound of formula (I): ##STR1## wherein: Z.sub.1, Z.sub.2, Z.sub.3, Z.sub.4, which may be identical or different, represent a group as defined in the description, X represents oxygen, S(O).sub.p, --(CH.sub.2).sub.n -- or --CH.sub.2 --Y--CH.sub.2 -- wherein p, n and Y are as defined in the description, A represents ##STR2## wherein m, R.sub.1, R.sub.2 and G are as defined in the description, their isomers and addition salts thereof with a pharmaceutically-acceptable acid, and medicinal products containing the same are useful in the treatment of diseases like depression, panic attacks, obsessive compulsive disorders, phobias, impulsive disorders, drug abuse or anxiety.

  式(I)的化合物：其中：Z₁，Z₂，Z₃，Z₄，可以相同也可以不同，表示如描述中定义的基团，X表示氧、S(O)ₚ、--(CH₂)ₙ--或--CH₂--Y--CH₂--其中p，n和Y如描述中定义，A表示其中m，R₁，R₂和G如描述中定义，它们的异构体及其与药用可接受的酸的加合盐，以及含有它们的药物产品在治疗抑郁症、恐慌发作、强迫性障碍、恐惧症、冲动障碍、药物滥用或焦虑等疾病方面是有用的。
• Structure–activity-relationship studies on dihydrofuran-fused perhydrophenanthrenes as an anti-Alzheimer’s disease agent
  作者：Kenji Sugimoto、Kosuke Tamura、Chihiro Tohda、Naoki Toyooka、Hideo Nemoto、Yuji Matsuya

  DOI：10.1016/j.bmc.2013.05.059

  日期：2013.8

  As an extended study on development of anti-Alzheimer's disease agent, we newly synthesized various dihydrofuran-fused perhydrophenanthrenes via o-quinodimethane chemistry. This study revealed that the introduction of carbon side-chain on 8-position or removal of the acetal moiety on 3-position arose a cytotoxicity on rat cortical neurons. On the other hand, the ethereal or thio-ethereal substituent on 8-position enhanced the elongation effect on A beta-damaged neurons. The necessity of the cyano group on 10b position was also proved in this structure-activity-relationship study. (C) 2013 Elsevier Ltd. All rights reserved.
• Nouveaux composés du benzocyclobutane, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent
  申请人：LES LABORATOIRES SERVIER

  公开号：EP0940386B1

  公开（公告）日：2002-05-22
• Dérivés du benzo[3,4]cyclobuta[1,2-c]pyrrole en tant qu' inhibiteurs de recapture de sérotonine
  申请人：LES LABORATOIRES SERVIER

  公开号：EP1038873B1

  公开（公告）日：2002-05-02