3-(2-hydroxy-phenyl)-3-methyl-but-3-en-2-one | 425628-66-6

• 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: 3-(2-hydroxy-phenyl)-3-methyl-but-3-en-2-one
• 英文别名: 4-(2-hydroxyphenyl)-3-methylbut-3-en-2-one；(E)-4-(2-hydroxyphenyl)-3-methylbut-3-en-2-one；4-(2-hydroxyphenyl)-3-methyl-(3E)-buten-2-one；4-(2-Hydroxy-phenyl)-3-methyl-but-3-en-2-on
• CAS: 425628-66-6
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: HPWANNGDYWQREM-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 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：

  3-(2-hydroxy-phenyl)-3-methyl-but-3-en-2-one 、 methyl 2-(3-((tert-butoxycarbonyl)oxy)-1-methyl-2-oxoindolin-3-yl)acrylate 在 四(三苯基膦)钯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 反应 36.0h， 以63%的产率得到
  参考文献：
  名称：

  Construction of Hydrodibenzo[b,d]furan Frameworks from Morita–Baylis–Hillman Carbonates of Isatins and o-Hydroxy Enones via Palladium and Brønsted Base Relay Catalysis

  摘要：

  DOI：

  10.1021/acs.orglett.1c03689
• 作为产物：
  描述：

  在 盐酸 、 水 作用下， 以20%的产率得到3-(2-hydroxy-phenyl)-3-methyl-but-3-en-2-one
  参考文献：
  名称：

  Reactivity of Allenylphosphonates toward Salicylaldehydes and Activated Phenols: Facile Synthesis of Chromenes and Substituted Butadienes

  摘要：

  The reaction of salicylaldehydes with allenylphosphonates in the presence of a base leads to a variety of phosphono-chromenes and allylic phosphonates. Optimization of reaction conditions reveals that DBU (base.) in DMSO (solvent) is the best combination in most cases, with DBU acting as an organocatalyst. PEG-400 also gave good results, but the yields were slightly lower than that in DMSO. Several of the key products have been characterized by single-crystal X-ray crystallography. Interconversion of E and Z isomers of phosphono-chromenes is demonstrated by P-31 NMR spectroscopy. A novel P-C bond cleavage reaction of some of these chromenes leading to substituted enones is also reported. In a few cases, phenol addition products are also isolated. In order to probe the pathways in the latter reaction, allenylphosphonates have also been treated with activated phenols in the presence of base to selectively afford either allylic phosphonyl ethers or vinylic phosphonyl ethers depending on the substituents on the allenylphosphonate. Theoretical calculations were consistent with experimental results. Finally, utilization of allylic phosphonyl ether in the Horner-Wadsworth-Emmons reaction to afford substituted trans-1,3-butadiene in good yields is demonstrated.

  DOI：

  10.1021/jo900896v

文献信息

• Asymmetric synthesis of α-chiral ketones by the reduction of enones with baker's yeast
  作者：Yasushi Kawai、Motoko Hayashi、Norihiro Tokitoh

  DOI：10.1016/s0957-4166(01)00537-7

  日期：2001.11

  asymmetric reduction of α,β-unsaturated ketones (enones) having a pyridyl ring affords the corresponding optically active α-substituted ketones (α-chiral ketones) with excellent stereoselectivity. The position of the heteroatom, as well as the bulk of the α-substituent, plays an important role in governing the stereoselectivity in the reduction of a carboncarbon double bond.

  贝克的酵母介导的具有吡啶环的α，β-不饱和酮（烯酮）的不对称还原提供了相应的旋光性α-取代的酮（α-手性酮），具有出色的立体选择性。杂原子的位置以及大部分的α-取代基在控制碳-碳双键还原的立体选择性方面起着重要作用。
• PESTICIDAL FLAVOBACTERIUM STRAIN AND BIOACTIVE COMPOSITIONS METABOLITES AND USES
  申请人：Marrone Bio Innovations, Inc.

  公开号：US20150031534A1

  公开（公告）日：2015-01-29

  Provided is a pesticidal Flavobacterium strain and bioactive compositions and metabolites derived therefrom as well as their methods of use for controlling pests.

  提供了一种杀虫的黄杆菌菌株及其衍生的生物活性组分和代谢产物，以及它们的使用方法，用于控制害虫。
• Pesticidal Flavobacterium strain and bioactive compositions metabolites and uses
  申请人：Marrone Bio Innovations, Inc.

  公开号：US11013236B2

  公开（公告）日：2021-05-25

  Provided is a pesticidal Flavobacterium strain and bioactive compositions and metabolites derived therefrom as well as their methods of use for controlling pests.

  本文提供了一种具有杀虫作用的黄杆菌菌株、生物活性组合物及其衍生代谢物，以及它们用于控制害虫的方法。
• Decker; v. Fellenberg, Justus Liebigs Annalen der Chemie, 1909, vol. 364, p. 22
  作者：Decker、v. Fellenberg

  DOI：——

  日期：——
• Tricyclic cyanoguanidines: synthesis, site of action and insecticidal activity of a novel class of reversible acetylcholinesterase inhibitors
  作者：Bruce L. Finkelstein、Eric A. Benner、Maura C. Hendrixson、Kevin T. Kranis、James J. Rauh、Maya R. Sethuraman、Stephen F. McCann

  DOI：10.1016/s0968-0896(01)00326-1

  日期：2002.3

  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.