7-羟基螺[苯并二氢吡喃-2,1-环戊烷]-4-酮 | 70441-03-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 7-羟基螺[苯并二氢吡喃-2,1-环戊烷]-4-酮
• 英文名称: 7-hydroxy-spiro<2H-1-benzopyran-2,1'-cyclopentane>-4(3H)-one
• 英文别名: 7-hydroxy-2-spiropentyl-2,3-dihydrochromen-4-one；7-hydroxyspiro[chroman-2,1'-cyclopentan]-4-one；7-hydroxyspiro[chroman-2,1′-cyclopentan]-4-one；7-hydroxyspiro[3H-chromene-2,1'-cyclopentane]-4-one
• CAS: 70441-03-1
• 化学式: C₁₃H₁₄O₃
• mdl: MFCD13152231
• 分子量: 218.252
• InChiKey: BWXZRLGTSDKAOP-UHFFFAOYSA-N

物化性质

• 熔点：
  174-175 °C
• 沸点：
  427.5±45.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  7-羟基螺[苯并二氢吡喃-2,1-环戊烷]-4-酮 在 potassium carbonate 、 lithium bromide 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 24.0h， 生成 7-(3-Anilino-2-hydroxy-propoxy)spiro[chromane-2,1'-cyclopentane]-4-one
  参考文献：
  名称：

  Synthesis and antitubercular activity of amino alcohol fused spirochromone conjugates

  摘要：

  A series of 21 new amino alcohol fused spirochromone conjugates have been synthesized, characterized with analytical data and evaluated their antimycobacterial activity against Mycobacterium tuberculosis (virulent strain H37Rv) in vitro. Some of the compounds exerted significant inhibition, in particular, compound 4f found to be the most potent derivative exhibiting MIC = 3.13 mu g/mL. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.12.073
• 作为产物：
  描述：

  2,4-二羟基苯乙酮 在 四氢吡咯 、 盐酸 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 生成 7-羟基螺[苯并二氢吡喃-2,1-环戊烷]-4-酮
  参考文献：
  名称：

  Synthesis, Structure–Activity Relationship Studies, and Antibacterial Evaluation of 4-Chromanones and Chalcones, as Well as Olympicin A and Derivatives

  摘要：

  On the basis of recently reported abyssinone II and olympicin A, a series of chemically modified flavonoid phytochemicals were synthesized and evaluated against Mycobacterium tuberculosis and a panel of Gram-positive and -negative bacterial pathogens. Some of the synthesized compounds exhibited good antibacterial activities against Gram-positive pathogens including methicillin resistant Staphylococcus aureus with minimum inhibitory concentration as low as 0.39 mu g/mL. SAR analysis revealed that the 2-hydrophobic substituent and the 4-hydrogen bond donor/acceptor of the 4-chromanone scaffold together with the hydroxy groups at 5- and 7-positions enhanced antibacterial activities; the 2',4'-dihydroxylated A ring and the lipophilic substituted B ring of chalcone derivatives were pharmacophoric elements for antibacterial activities. Mode of action studies performed on selected compounds revealed that they dissipated the bacterial membrane potential, resulting in the inhibition of macromolecular biosynthesis; further studies showed that selected compounds inhibited DNA topoisomerase IV, suggesting complex mechanisms of actions for compounds in this series.

  DOI：

  10.1021/jm500853v

文献信息

• Design, Synthesis and Biological Investigation of Flavone Derivatives as Potential Multi-Receptor Atypical Antipsychotics
  作者：Lanchang Gao、Zhengge Yang、Jiaying Xiong、Chao Hao、Ru Ma、Xin Liu、Bi-Feng Liu、Jian Jin、Guisen Zhang、Yin Chen

  DOI：10.3390/molecules25184107

  日期：——

  was also endowed with low to moderate activities on 5-HT2C, α1, and H1 receptors, indicating a low liability to induce side effects such as weight gain, orthostatic hypotension and QT prolongation. In vivo behavioral studies suggested that 6j has favorable effects in alleviating the schizophrenia-like symptoms without causing catalepsy. Taken together, compound 6j has the potential to be further developed

  通过使用多巴胺受体和血清素受体之间的多受体亲和策略，设计了一系列新型黄酮衍生物作为潜在的广谱抗精神病药。其中，7-(4-(4-(6-fluorobenzo[d]isoxazol-3-yl) piperidin-1-yl) butoxy)-2,2-dimethylchroman-4-one (6j) 表现出有希望的临床前特征. 化合物 6j 不仅对多巴胺 D2、D3 和血清素 5-HT1A、5-HT2A 受体表现出高亲和力，而且对 5-HT2C、α1 和 H1 受体也具有低至中度的活性，表明诱导的可能性较低副作用如体重增加、体位性低血压和 QT 间期延长。体内行为研究表明，6j 在减轻精神分裂症样症状方面具有良好的作用，而不会引起僵住症。综合起来，
• Concise and diversity-oriented synthesis of novel scaffolds embedded with privileged benzopyran motif
  作者：Sung Kon Ko、Hwan Jong Jang、Eunha Kim、Seung Bum Park

  DOI：10.1039/b606341a

  日期：——

  A branching DOS strategy for an unbiased natural product-like library with embedded privileged benzopyran motif was established to provide complexity and diversity of resulting heterocycles with desired drug-likeness. The importance of skeletal diversity conducted on a privileged substructure was demonstrated through the biological evaluation of a small molecule library representing 22 unique core skeletons via in vitro cytotoxicity assay.

  建立了一种分枝的DOS策略，用于制备无偏倚的、类似天然产物库的分子库，其中嵌入特权苯并吡喃结构基元，以提供具有期望的类药性的杂环化合物的复杂性和多样性。通过体外细胞毒性检测，对代表22种独特核心骨架的小分子库进行生物活性评估，展示了以特权子结构为基础的骨架多样性的重要性。
• COMPOUNDS WITH EMBEDDED BENZOPYRAN MOTIF FOR CORE STRUCTURES AND PREPARATION METHOD THEREOF
  申请人：Park Seung Bum

  公开号：US20090326015A1

  公开（公告）日：2009-12-31

  The present invention relates to a compound having benzopyran core, a preparation method of the derivatives by liquid phase synthesis and solid phase synthesis through diversity-oriented synthesis, and an anticancer agent comprising the compound that exhibit excellent cytotoxicity against cancer cells.

  本发明涉及一种具有苯并吡喃核的化合物，通过多样性定向合成的液相合成和固相合成的衍生物制备方法，以及包含该化合物的抗癌剂，该化合物对癌细胞表现出优异的细胞毒性。
• Construction of a Polyheterocyclic Benzopyran Library with Diverse Core Skeletons through Diversity-Oriented Synthesis Pathway
  作者：Sangmi Oh、Hwan Jong Jang、Sung Kon Ko、Yeonjin Ko、Seung Bum Park

  DOI：10.1021/cc100044w

  日期：2010.7.12

  In this study, a divergent and practical solid-phase parallel diversity-oriented synthesis (DOS) strategy was successfully applied for the construction of five discrete core skeletons embedded with privileged benzopyranyl substructure. The diversity of these core skeletons was expanded through the introduction of various substituents at the R, R(1), and R(2) positions from a single key intermediate

  在这项研究中，发散和实用的固相平行分集定向合成（DOS）策略已成功地应用于构建五个嵌入有特权苯并吡喃基亚结构的离散核骨架。这些核心骨架的多样性通过在五个不同途径中的单个关键中间体在R，R（1）和R（2）位置处引入各种取代基而得到扩展。更重要的是，我们通过使用库到库的概念，通过核心骨架本身的转换来有效地最大化了分子多样性，并创建了具有相同构件的独特小分子集合。构建了一个434个成员的多杂环苯并吡喃文库，规模约为10 mg，具有进一步多样化的潜力。无需进一步纯化，
• A new and efficient general method for the synthesis of 2-spirobenzopyrans: First synthesis of cyclic analogues of precocene I and related compounds
  作者：Suneel Y Dike、Jaysukhlal R Merchant、Niteen Y Sapre

  DOI：10.1016/s0040-4020(01)86481-4

  日期：1991.1

  A new synthesis of spirobenzopyran has been accomplished by Friedel- Crafts reaction of various m-dihydroxybenzenes and cycloalkylidene acetic acid in the presence of a Lewis acid.

  在路易斯酸的存在下，各种间二羟基苯与环亚烷基乙酸的弗里德尔工艺合成反应完成了螺并苯并吡喃的新合成。