2-(2-hydroxybenzylidene)cyclohexan-1-one | 50355-44-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(2-hydroxybenzylidene)cyclohexan-1-one
• 英文别名: 2-(2-hydroxybenzylidene)cyclohexanone；2-[(2-Hydroxyphenyl)methylidene]cyclohexan-1-one
• CAS: 50355-44-7
• 化学式: C₁₃H₁₄O₂
• 分子量: 202.253
• InChiKey: FJCSUUJWLABYAE-UHFFFAOYSA-N

物化性质

• 熔点：
  125-127 °C(Solv: benzene (71-43-2))
• 沸点：
  383.1±31.0 °C(Predicted)
• 密度：
  1.195±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-hydroxybenzylidene)cyclohexan-1-one 在 sodium acetate 、 一水合肼 、 溶剂黄146 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 46.0h， 生成 2-(2-benzylidene-3-((diphenylmethylene)hydrazineylidene)-2,3,6,7,8,9-hexahydro-5H-thiazolo[2,3-b]quinazolin-5-yl)phenol
  参考文献：
  名称：

  Synthesis of Novel 6,7,8,9-Tetrahydro-5H-5-hydroxyphenyl-2-benzylidine-3-substituted Hydrazino Thiazolo (2,3-b) Quinazoline as Potent Antinociceptive and Anti-inflammatory Agents

  摘要：

  合成了一系列6,7,8,9-四氢-5H-5-羟基苯基-2-苄基亚胺-3-取代的肼基噻唑(2,3-b)喹唑啉，以满足抗炎和镇痛特性所必需的结构要求。合成的一系列杂环化合物6,7,8,9-四氢-5H-5-羟基苯基-2-苄基亚胺-3-取代的肼基噻唑(2,3-b)喹唑啉是通过6,7,8,9-四氢-5H-5-羟基苯基噻唑(2,3-b)喹唑啉-3(2H)-酮与适当的肼水合物和酮/醛在无水醋酸钠和冰醋酸存在下反应而得，如方案1所示。通过尾翻转技术评估了它们的镇痛活性，通过卡拉胶诱导的爪肿胀试验评估了抗炎活性，通过已报道的方案确定其溃疡指数。化合物显示出最低的溃疡指数（$0.51{\pm}1.63$，$0.48{\pm}1.28$ 和 $0.50{\pm}1.53$）。6,7,8,9-四氢-5H-5-羟基苯基-2-苄基亚胺-3-(N'-3-戊烯肼)噻唑(2,3-b)喹唑啉和6,7,8,9-四氢-5H-5-羟基苯基-2-苄基亚胺-3-(N'-2-戊烯肼)噻唑(2,3-b)喹唑啉表现出最强的镇痛和抗炎活性。

  DOI：

  10.5012/bkcs.2010.31.11.3265
• 作为产物：
  描述：

  环己酮 、 水杨醛 在 sodium hydroxide 作用下， 生成 2-(2-hydroxybenzylidene)cyclohexan-1-one
  参考文献：
  名称：

  Synthesis of Novel 6,7,8,9-Tetrahydro-5H-5-hydroxyphenyl-2-benzylidine-3-substituted Hydrazino Thiazolo (2,3-b) Quinazoline as Potent Antinociceptive and Anti-inflammatory Agents

  摘要：

  合成了一系列6,7,8,9-四氢-5H-5-羟基苯基-2-苄基亚胺-3-取代的肼基噻唑(2,3-b)喹唑啉，以满足抗炎和镇痛特性所必需的结构要求。合成的一系列杂环化合物6,7,8,9-四氢-5H-5-羟基苯基-2-苄基亚胺-3-取代的肼基噻唑(2,3-b)喹唑啉是通过6,7,8,9-四氢-5H-5-羟基苯基噻唑(2,3-b)喹唑啉-3(2H)-酮与适当的肼水合物和酮/醛在无水醋酸钠和冰醋酸存在下反应而得，如方案1所示。通过尾翻转技术评估了它们的镇痛活性，通过卡拉胶诱导的爪肿胀试验评估了抗炎活性，通过已报道的方案确定其溃疡指数。化合物显示出最低的溃疡指数（$0.51{\pm}1.63$，$0.48{\pm}1.28$ 和 $0.50{\pm}1.53$）。6,7,8,9-四氢-5H-5-羟基苯基-2-苄基亚胺-3-(N'-3-戊烯肼)噻唑(2,3-b)喹唑啉和6,7,8,9-四氢-5H-5-羟基苯基-2-苄基亚胺-3-(N'-2-戊烯肼)噻唑(2,3-b)喹唑啉表现出最强的镇痛和抗炎活性。

  DOI：

  10.5012/bkcs.2010.31.11.3265

文献信息

• Modified calcium oxide as stable solid base catalyst for Aldol condensation reaction
  作者：YING TANG、JINGFANG XU、XUEFAN GU

  DOI：10.1007/s12039-013-0362-5

  日期：2013.3

  A highly efficient and stable solid-base catalyst for Aldol condensation was prepared by modifying commercial CaO with benzyl bromide in a simple way. It was found that modified CaO can effectively catalyse the Aldol condensation of cyclohexanone and benzaldehyde, as well as various benzaldehydes, to produce 2-benzylidenecyclohexanone with a good selectivity and high yield. Higher yield of 95.8% was obtained over modified CaO after 3 h, which is short compared with the yield of 92.1% after 12 h over commercial CaO. The influence of several reaction parameters, such as temperature, catalyst loading, was investigated. The humidity test over modified CaO reveals that the basic centres of modified CaO are stable for CO2 and moisture. From the results of Fourier transform-infrared (FT-IR) and Thermogravity analysis (TG) characterization, the modifier was bonded on surface of CaO chemically and almost no Ca(OH)2 formed during the modification process. The type of aldehyde has great influence on the yield of aldol condensation.

  一种高效稳定的固体碱催化剂用于阿尔多尔缩合反应，通过简单地用溴化苄修饰商业氢氧化钙（CaO）制备而成。研究发现，改性后的CaO能够有效催化环己酮与苯甲醛及各种苯甲醛的阿尔多尔缩合，生成2-苄基环己酮，具有良好的选择性和高产率。在3小时内，改性CaO的产率达到95.8%，相比之下，商业CaO在12小时后的产率仅为92.1%。还研究了温度、催化剂负载等多种反应参数的影响。对改性CaO的湿度测试表明，其基本中心对二氧化碳和水分是稳定的。通过傅里叶变换红外光谱（FT-IR）和热重分析（TG）表征的结果显示，修饰剂与CaO表面发生了化学结合，并且在修饰过程中几乎没有形成Ca(OH)2。醛的种类对阿尔多尔缩合的产率有很大影响。
• Synthesis and Biological Activities of Some New C-Aminomethylation of 5H-5-Aryl-6,7,8,9-tetrahydrothiazolo[2,3-b]quinazolin-3(2H)-one and 6H-6-Aryl-2,3,7,8,9,10-hexahydrothiazino[2,3-b]quinazolin-4(3H)-one
  作者：Damerakonda Kumaraswamy、V. Mallareddy

  DOI：10.14233/ajchem.2016.19939

  日期：——

  The synthesis of 5H-5-aryl-6,7,8,9-tetrahydrothiazolo[2,3-b]quinazolin-3(2H)-one and 6H-6-aryl-2,3,7,8,9,10-hexahydrothiazino[2,3-b]quinazolin-4(3H)-one, reaction between 4-aryl-3,4,5,6,7,8-hexahydroquinazolin-2-thione and methyl chloroacetate and ethyl b-bromo propionate. The Mannich reaction on 5H-5-aryl-6,7,8,9-tetrahydrothiazolo[2,3-b]quinazolin-3(2H)-one and 6H-6-aryl-2,3,7,8,9,10-hexahydrothiazino[2,3-b]quinazolin-4(3H)-one in ethanol, aqueous formaldehyde and different secondary amines yielded a single product C-Mannich base in each case. The obtained C-Mannich bases (compounds VIII and X) have been characterized on the basis of analytical spectral data. These C-Mannich bases have been screened for their antibacterial, antifungal, anti-inflammatory and analgesic activities.

  5H-5-芳基-6,7,8,9-四氢噻唑并[2,3-b]喹唑啉-3(2H)-酮和 6H-6-芳基-2,3,7,8,9,10-六氢噻唑并[2,3-b]喹唑啉-4(3H)-酮的合成，4-芳基-3,4,5,6,7,8-六氢喹唑啉-2-硫酮与氯乙酸甲酯和 b-溴丙酸乙酯的反应。在乙醇、甲醛水溶液和不同的仲胺中，5H-5-芳基-6,7,8,9-四氢噻唑并[2,3-b]喹唑啉-3(2H)-酮和 6H-6-芳基-2,3,7,8,9,10-六氢噻唑并[2,3-b]喹唑啉-4(3H)-酮的曼尼希反应均产生了单一产物 C-曼尼希碱。根据分析光谱数据，对获得的 C-Mannich 碱（化合物 VIII 和 X）进行了表征。对这些 C-Mannich 碱进行了抗菌、抗真菌、抗炎和镇痛活性筛选。
• pH dependent structural interconversion of 2-(2-hydroxy-benzylidene)-cyclohexan-1-one: Crystal structures and spectroscopic investigation
  作者：Ana-Maria Pană、Iulia Păuşescu、Sergiu Shova、Valentin Badea、Ramona Tudose、Mihaela Silion、Otilia Costişor、Liliana Cseh

  DOI：10.1016/j.molstruc.2017.02.003

  日期：2017.6

  The behavior of 2-(2-hydroxy-benzylidene)-cyclohexan-1-one (BC) in the acidic and basic media was investigated. In acidic conditions a new dimeric structure 4′a-methoxy-2,2′,3,3′,4′,4′a,9′,9′a-octahydro-1H, 1′H-4,9′-bixanthene (XTC) was isolated. The structures of BC and XTC were confirmed by single crystal X-ray diffraction and NMR. In basic conditions, unprotonated specie (BC − ) was characterized by

  摘要 研究了2-(2-羟基-亚苄基)-环己-1-酮(BC)在酸性和碱性介质中的行为。在酸性条件下，新的二聚结构 4'a-甲氧基-2,2',3,3',4',4'a,9',9'a-octahydro-1H, 1'H-4,9'-分离出二氧杂蒽（XTC）。BC和XTC的结构经单晶X射线衍射和核磁共振证实。在碱性条件下，未质子化物质 (BC - ) 通过 NMR、UV-Vis 和荧光光谱进行表征；BC 可以用作 pH 传感器。
• 2,2′-Spirobis[chromene] Derivatives Chemistry and Their Relation with the Multistate System of Anthocyanins
  作者：Artur J. Moro、A. Jorge Parola、Fernando Pina、Ana-Maria Pana、Valentin Badea、Iulia Pausescu、Sergiu Shova、Liliana Cseh

  DOI：10.1021/acs.joc.7b00634

  日期：2017.5.19

  The chemistry of 2,2′-spirobis[chromene] derivatives is intimately related to the one of anthocyanins and similar compounds. The 2,2′-spirobis[chromene] species plays a central role in the network of chemical reactions connecting two different flavylium-based multistate systems. In the present work, a new asymmetric 2,2′-spirobis[chromene] intermediate possessing a constrained propylenic bridge between

  2,2'-螺双[chromene]衍生物的化学性质与花色苷和类似化合物之一密切相关。2,2'-spirobis [chromene]物种在连接两个不同的基于黄酮的多态系统的化学反应网络中发挥着核心作用。在目前的工作中，分离了一种新的不对称的2,2'-螺双[chromene]中间体，该中间体在碳3和3'之间具有受限制的亚丙基桥，并通过化学方法研究了其在花色苷类多态化学反应中的关键作用。吸收光谱，停止流，NMR和X射线晶体学的共轭。已经证实，亚丙基桥对于稳定螺环二苯甲基物种是必不可少的。此外，在酸性条件下，两个顺式-反式鉴定了苯乙烯丁香鎓异构体，可以将其与光直接相互转化为彼此。这是关于苯乙烯基部分上具有光异构化的苯乙烯基黄铵阳离子的首次报道。
• Synthesis, Characterization, and Antiproliferative Properties of New Bio-Inspired Xanthylium Derivatives
  作者：Claudia Koch、Diana-Maria Dreavă、Anamaria Todea、Francisc Péter、Mihai Medeleanu、Iulia Păușescu、Corina Samoilă、Ioan Ovidiu Sîrbu

  DOI：10.3390/molecules28031102

  日期：——

  were synthesized, and their photochromic and biological properties were investigated. The UV-Vis spectroscopy and the direct and reverse pH-jumps studies confirmed the halochromic properties and the existence of different molecular species. A network of chemical reactions of these species was proposed. Furthermore, the antiproliferative properties of both compounds were evaluated using P19 murine embryocarcinoma

  Xanthylium 衍生物是具有光致变色特性的姜黄素类似物。与花青素类似，它们遵循相同的化学物质多态网络，这些化学物质在外部刺激下可逆地相互转化。在目前的工作中，姜黄素的两种新的不对称单羰基类似物，4-(4-hydroxy-3-metoxybenzylidene)-1,2,3,4-tetrahydroxanthylium chloride (compound 3) 和 4-(4-hydroxybenzylidene)-6-合成了 methoxy-1,2,3,4-tetrahydroxanthylium chloride（化合物 4），并研究了它们的光致变色和生物学性质。紫外-可见光谱和直接和反向 pH 跳跃研究证实了光变色特性和不同分子种类的存在。提出了这些物种的化学反应网络。此外，使用 P19 小鼠胚胎癌细胞评估这两种化合物的抗增殖特性，并相互比较。结果表明，两种新的苍耳衍生物都可以改变