4-(2-hydroxy-5-methyl-phenyl)-but-3-en-2-one | 790720-66-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 4-(2-hydroxy-5-methyl-phenyl)-but-3-en-2-one
• 英文别名: (E)-4-(2-hydroxy-5-methylphenyl)but-3-en-2-one；(E)-4-(2-hydroxy-5-methylphenyl)but-3-en-2-on；4-(2-Hydroxy-5-methyl-phenyl)-but-3-en-2-on；4-(2-Hydroxy-5-methylphenyl)but-3-en-2-one
• CAS: 790720-66-0
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: ZSFKFODBLVOPMW-SNAWJCMRSA-N

物化性质

• 熔点：
  132 °C
• 沸点：
  331.2±27.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  4-(2-hydroxy-5-methyl-phenyl)-but-3-en-2-one 在 rose bengal 、 氧气 、 caesium carbonate 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以75%的产率得到5-hydroxy-5-methyl-1-[(1E)-4-oxopent-1-en-1-yl]-7-oxabicyclo[4.1.0]hept-3-en-2-one
  参考文献：
  名称：

  通过光氧化过程 将苯酚多催化脱芳香化为环氧喹啉†

  摘要：

  据报道，在绿色LED灯下，在玫瑰红和碳酸铯的存在下，对取代的酚进行了多催化光氧化。该转化使得能够引入单线态氧的两个原子，并导致以立体选择性的方式一锅合成环氧喹啉。

  DOI：

  10.1039/c9cc03068a
• 作为产物：
  描述：

  5-甲基水杨醛 、 丙酮 在 sodium hydroxide 作用下， 以 水 为溶剂， 以89%的产率得到4-(2-hydroxy-5-methyl-phenyl)-but-3-en-2-one
  参考文献：
  名称：

  Tricyclic cyanoguanidines: synthesis, site of action and insecticidal activity of a novel class of reversible acetylcholinesterase inhibitors

  摘要：

  Bridged-tricyclic cyanoguanidines 1 were found to be active as insecticides. The preparation and structure-activity relationships of oxacyclic (X=O) and carbocyclic (X=CH2) analogues of 1 is described. Compounds 1 were found to inhibit acetylcholinesterase with IC50 values comparable to the organophosphate Paraoxon. Unlike organophosphates. cyanoguanidines 1 were shown to reversibly bind acetylcholinesterase. This mode of action is shared by the structurally-related natural product Huperzine A. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00326-1

文献信息

• Palladium(II)-Catalyzed 1,4-Addition of Arylboronic Acids to β-Arylenones for Enantioselective Synthesis of 4-Aryl-4H-chromenes
  作者：Takashi Nishikata、Yasunori Yamamoto、Norio Miyaura

  DOI：10.1002/adsc.200600622

  日期：2007.7.2

  carried out at 0–25 °C in the presence of a dicationic palladium(II) catalyst, [Pd(S,S-chiraphos)(PhCN)2](SbF6)2. Addition of a silver salt such as silver tetrafluoroborate [AgBF4] or silver hexafluoroantimonate [AgSbF6] (5–10 mol %) was effective to achieve high enantioselectivities at low temperatures (92–99 % ee) and to reduce the catalyst loading to 0.05 mol %. The protocol provided a simple access to

  在阳离子钯（II）催化剂[Pd（S，S -chiraphos）存在下，在0–25°C的条件下将芳基硼酸与β-芳烯酮进行对映选择性的1,4-加成反应，得到β-二芳基酮。（PhCN）2 ]（SbF 6）2。添加银盐，例如四氟硼酸银[AgBF 4 ]或六氟锑酸银[AgSbF 6 ]（5-10 mol％），可以有效地在低温下（92-99％ee）实现高对映选择性，并降低催化剂的负载量。 0.05摩尔％。该协议提供了对4-芳基-4 H-色烯的简单访问。旋光色烯可通过高达99％的ee合成。 芳基硼酸和β-（2-羟基芳基）-α，β-不饱和酮之间的1,4-加合物的脱水反应
• Asymmetric Dearomative Cascade Multiple Functionalizations of Activated <i>N</i>-Alkylpyridinium and <i>N</i>-Alkylquinolinium Salts
  作者：Xue Song、Ru-Jie Yan、Wei Du、Ying-Chun Chen

  DOI：10.1021/acs.orglett.0c02828

  日期：2020.10.2

  An enantioselective cascade reaction of N-alkylpyridinium and -quinolinium salts with o-hydroxybenzylideneacetones to access fused polyheterocycles through cross dienamine-mediated addition followed by trapping of the dearomatized enamine-type intermediates and aminal formation has been developed. A cascade assembly of N-benzyl-4-methylpyridinium salt and cyclic 2,4-dienones is further disclosed to

  已开发出N-烷基吡啶鎓盐和-喹啉鎓盐与邻羟基苄叉基丙酮的对映选择性级联反应，通过交叉二烯胺介导的加成反应，然后捕获脱芳族化的烯胺型中间体和缩醛形成，从而进入稠合多杂环。还公开了N-苄基-4-甲基吡啶盐和环状2，4-二壬烯的级联组装，以通过重复的脱芳香化作用和芳构化活化作用给出桥连的骨架。
• Dually activated Michael-Michael-acetalization cascade: facile and highly diastereoselective construction of tetrahydro-6-hydroxyl-6H-benzo[c]chromen-9-one polycyclic scaffold
  作者：Jian Liu、Sai-Shuai Wen、Jing Wang、Jun-An Xiao、Shao-Jie Huang、Hua Yang

  DOI：10.1016/j.tet.2015.05.014

  日期：2015.7

  A Michael-Michael-acetalization cascade between 4-(2-hydroxyphenyl)but-3-en-2-ones and alpha,beta-unsaturated aldehydes via a novel dual activation mode promoted by pyrrolidine was successfully established. Consequently, various novel tetrahydro-6-hydroxyl-6H-benzo[c]chromen-9-one derivatives were prepared in excellent diastereoselectivities and moderate to good yields. Further diverse modification of the resulting tricyclic scaffolds provided a facile pathway to achieve a variety of tetrahydro-6-hydroxyl-6H-benzo[c]chromen-9-one analogs. (C) 2015 Elsevier Ltd. All rights reserved.
• Borsche; Merkwitz, Chemische Berichte, 1904, vol. 37, p. 3182
  作者：Borsche、Merkwitz

  DOI：——

  日期：——
• Construction of Hydrodibenzo[<i>b</i>,<i>d</i>]furan Frameworks from Morita–Baylis–Hillman Carbonates of Isatins and <i>o</i>-Hydroxy Enones via Palladium and Brønsted Base Relay Catalysis
  作者：Ze-Liang He、Peng Chen、Zhi-Chao Chen、Wei Du、Ying-Chun Chen

  DOI：10.1021/acs.orglett.1c03689

  日期：2022.1.14