(E)-4-(2-Hydroxy-3-methyl-phenyl)-but-3-en-2-one | 500902-77-2

• 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: (E)-4-(2-Hydroxy-3-methyl-phenyl)-but-3-en-2-one
• 英文别名: 4-(2-Hydroxy-3-methylphenyl)but-3-en-2-one
• CAS: 500902-77-2
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: SFUMQDJDHRXEDP-UHFFFAOYSA-N

物化性质

• 沸点：
  325.8±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：

  (E)-4-(2-Hydroxy-3-methyl-phenyl)-but-3-en-2-one 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 2-methyl-6-(3-methyl-4,5-dihydro-1H-pyrazol-5-yl)phenol
  参考文献：
  名称：

  Design and synthesis of N-phenylacetyl (sulfonyl) 4,5-dihydropyrazole derivatives as potential antitumor agents

  摘要：

  A series of novel N-phenylacetyl (sulfonyl) 4,5-dihydropyrazole derivatives as potential telomerase inhibitors were synthesized. The bioassay tests show that compound 4a exhibited high activity against human gastric cancer cell SGC-7901, liver cancer Hep-G2 and human prostate PC-3 cell lines with IC50 values of 21.23 +/- 0.99, 29.43 +/- 0.32 and 30.89 +/- 1.07 mu M, respectively. All title compounds were assayed for telomerase inhibition by a modified TRAP assay, the results show that compound 4a can inhibit telomerase with IC50 value of 4.0 +/- 0.32 mu M. Docking simulation was performed to position compound 4a into the telomerase (3DU6) active site to determine the probable binding model. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.066
• 作为产物：
  描述：

  邻甲酚 在 三乙胺 、 sodium hydroxide 、 magnesium chloride 作用下， 以 水 、 乙腈 为溶剂， 反应 22.0h， 生成 (E)-4-(2-Hydroxy-3-methyl-phenyl)-but-3-en-2-one
  参考文献：
  名称：

  Pd（II）催化的不对称Wacker型环化反应制备具有联苯四恶唑啉配体的2-乙烯基苯并二氢吡喃衍生物

  摘要：

  本文介绍了一种有效的方法，通过使用螯合诱导的轴向手性四恶唑啉配体，通过Pd（II）催化的不对称Wacker型环化制备手性苯并二氢吡喃衍生物。在优化的条件下，可获得高达80％的收率和高达92％的ee。这是在这种转化中利用邻三取代的3-丁烯基酚作为底物的第一个例子。

  DOI：

  10.1016/j.tet.2012.03.077

文献信息

• One-pot reaction for the concise synthesis of spiro[benzofuran-2,2′-naphthalen]-1′-one derivatives
  作者：Jiaxing Hu、Dandan Liu、Wengang Xu、Fanglin Zhang、Hua Zheng

  DOI：10.1016/j.tet.2014.08.023

  日期：2014.10

  synthesize various spiro[benzofuran-2,2′-naphthalen]-1′-one derivatives from the three-component reaction of tetralones, 2-hydroxyphenyl functionalized α,β-unsaturated ketones, and iodine. One C–C bond and one C–O bond have formed during this process. The notable features of this protocol are simple and mild reaction conditions, applicable to a wide range of readily available starting materials, good yields

  已开发出一种新颖的一锅两步方案，以从四氢萘酮，2-羟基苯基官能化的α，β-不饱和基团的三组分反应合成各种螺[苯并呋喃-2,2'-萘] -1'-一衍生物酮和碘。在此过程中形成了一个C–C键和一个C–O键。该方案的显着特点是反应条件简单温和，适用于各种现成的起始原料，良好的收率（高达91％）和出色的立体选择性（高达97：3）。
• Pd(II)-catalyzed asymmetric Wacker-type cyclization for the preparation of 2-vinylchroman derivatives with biphenyl tetraoxazoline ligands
  作者：Qingchuan Liu、Ke Wen、Zhenfeng Zhang、Zhengxing Wu、Yong Jian Zhang、Wanbin Zhang

  DOI：10.1016/j.tet.2012.03.077

  日期：2012.7

  This article describes an efficient method for the preparation of chiral chroman derivatives by the Pd(II)-catalyzed asymmetric Wacker-type cyclization using a chelation-induced axially chiral tetraoxazoline ligand. Under the optimized conditions, up to 80% yield and up to 92% ee were obtained. This is the first example to utilize o-trisubstituted 3-butenylphenols as substrates in such transformation

  本文介绍了一种有效的方法，通过使用螯合诱导的轴向手性四恶唑啉配体，通过Pd（II）催化的不对称Wacker型环化制备手性苯并二氢吡喃衍生物。在优化的条件下，可获得高达80％的收率和高达92％的ee。这是在这种转化中利用邻三取代的3-丁烯基酚作为底物的第一个例子。
• Design and synthesis of N-phenylacetyl (sulfonyl) 4,5-dihydropyrazole derivatives as potential antitumor agents
  作者：Xin-Hua Liu、Ban-Feng Ruan、Jing-Xin Liu、Bao-An Song、Ling-Hong Jing、Jun Li、Yang Yang、Hai-Liang Zhu、Xing-Bao Qi

  DOI：10.1016/j.bmcl.2011.03.066

  日期：2011.5

  A series of novel N-phenylacetyl (sulfonyl) 4,5-dihydropyrazole derivatives as potential telomerase inhibitors were synthesized. The bioassay tests show that compound 4a exhibited high activity against human gastric cancer cell SGC-7901, liver cancer Hep-G2 and human prostate PC-3 cell lines with IC50 values of 21.23 +/- 0.99, 29.43 +/- 0.32 and 30.89 +/- 1.07 mu M, respectively. All title compounds were assayed for telomerase inhibition by a modified TRAP assay, the results show that compound 4a can inhibit telomerase with IC50 value of 4.0 +/- 0.32 mu M. Docking simulation was performed to position compound 4a into the telomerase (3DU6) active site to determine the probable binding model. (C) 2011 Elsevier Ltd. All rights reserved.