4-[(Z)-2-(4-Methanesulfonyl-phenyl)-1-phenyl-but-1-enyl]-phenol | 760948-59-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 4-[(Z)-2-(4-Methanesulfonyl-phenyl)-1-phenyl-but-1-enyl]-phenol
• 英文别名: 4-(2-(4-(Methylsulfonyl)phenyl)-1-phenylbut-1-enyl)phenol；4-[(Z)-2-(4-methylsulfonylphenyl)-1-phenylbut-1-enyl]phenol
• CAS: 760948-59-2
• 化学式: C₂₃H₂₂O₃S
• 分子量: 378.492
• InChiKey: NCYNUGBKDQITPZ-FCQUAONHSA-N

物化性质

• 熔点：
  188-190 °C
• 沸点：
  545.1±42.0 °C(Predicted)
• 密度：
  1.198±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  62.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酰氯 、 4-[(Z)-2-(4-Methanesulfonyl-phenyl)-1-phenyl-but-1-enyl]-phenol 在 三乙胺 作用下， 以 乙醚 为溶剂， 反应 1.5h， 以72%的产率得到Acetic acid 4-[(Z)-2-(4-methanesulfonyl-phenyl)-1-phenyl-but-1-enyl]-phenyl ester
  参考文献：
  名称：

  Methylsulfonyl and Hydroxyl Substituents InduceZ-Stereocontrol in the McMurry Olefination Reaction

  摘要：

  具有甲基磺酰基和羟基取代基的芳基酮，能够引导立体控制，在Zn-TiCl4催化的McMurry反应中选择性地生成Z-烯烃。

  DOI：

  10.1055/s-2004-829087
• 作为产物：
  描述：

  1-[4-(甲硫基)苯基]-1-丙酮 在 Oxone 、 四氯化钛 、 锌 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 17.5h， 生成 4-[(Z)-2-(4-Methanesulfonyl-phenyl)-1-phenyl-but-1-enyl]-phenol
  参考文献：
  名称：

  Methylsulfonyl and Hydroxyl Substituents InduceZ-Stereocontrol in the McMurry Olefination Reaction

  摘要：

  具有甲基磺酰基和羟基取代基的芳基酮，能够引导立体控制，在Zn-TiCl4催化的McMurry反应中选择性地生成Z-烯烃。

  DOI：

  10.1055/s-2004-829087

文献信息

• Design and synthesis of acyclic triaryl (Z)-olefins: a novel class of cyclooxygenase-2 (COX-2) inhibitors
  作者：Md. Jashim Uddin、P.N. Praveen Rao、Edward E. Knaus

  DOI：10.1016/j.bmc.2004.08.021

  日期：2004.11

  A group of acyclic 2-alkyl-1, 1-diphenyl-2-(4-methylsulfonylphenyl)ethenes was designed for evaluation as selective cyclooxygenase-2 (COX-2) inhibitors. In vitro COX-1 and COX-2 isozyme inhibition structure-activity studies identified 1,1-diphenyl-2(4-methylsulfonylphenyl)hex-1-ene as a highly potent (IC50 = 0.014muM), and an extremely selective [COX-2 selectivity index (SI) >7142], COX-2 inhibitor that showed superior anti-inflammatory (A1) activity (ID50 = 2.5 mg/kg) relative to celecoxib (ID50 = 10.8mg/kg). This initial study was extended to include the design of a structurally related group of acyclic triaryl (Z)-olefins possessing an acetoxy (OAc) substituent at the para-position of the C-1 phenyl ring that is cis to a C-2 4-methylsulfonylphenyl substituent. COX-1 and COX-2 inhibition studies showed that (Z)-1-(4-acetoxyphenyl)-1-phenyl-2-(4-methylsulfonylphenyl)but-1-ene [(Z)-13b] is a potent (COX-1 IC50 = 2.4muM; COX-2 IC50 = 0.03 muM), and selective (COX-2 SI = 81), COX-2 inhibitor which is a potent AI agent (ID50 = 4.1 mg/kg) with equipotent analgesic activity to celecoxib. A molecular modeling (docking) study showed that the SO2Me substituent of (Z)-13b inserts deep inside the 2degrees-pocket of the COX-2 active site where one of the O-atoms of SO, group undergoes a H-bonding interaction with Phe(518). The p-OAc substituent on the C-1 phenyl ring is oriented in a hydrophobic pocket comprised of Met(522), Gly(526), Trp(387), Tyr(348), and Tyr(385), and the C-2 ethyl substituent is oriented towards the mouth of the COX-2 channel in the vicinity of amino acid residues Arg(12)0, Leu(531), and Val(349). Structure-activity data acquired indicate that a (Z)olefin having cis C-1 4-acetoxyphenyl (phenyl) and C-2 4-methylsulfonylphenyl substituents, and a C-1 phenyl substituent in conjunction with either a C-2 hydrogen or short alkyl substituent provides a novel template to design acyclic olefinic COX-2 inhibitors that, like aspirin, have the potential to acetylate COX-2. (C) 2004 Elsevier Ltd. All rights reserved.
• Triaryl (Z)-olefins suitable for radiolabeling with carbon-11 or fluorine-18 radionuclides for positron emission tomography imaging of cyclooxygenase-2 expression in pathological disease
  作者：Khaled R.A. Abdellatif、Carlos A. Velázquez、Zhangjian Huang、Morshed A. Chowdhury、Edward E. Knaus

  DOI：10.1016/j.bmcl.2010.06.155

  日期：2010.9

  A group of (Z)-1,1-diphenyl-2-(4-methylsulfonylphenyl) alk-1-enes were synthesized using methodologies that will allow incorporation of a [(11)C] OCH(3) substituent at the para-position of the C-1 phenyl ring, a [(11)C] SO(2)CH(3) substituent at the para-position of the C-2 phenyl ring, a [(18)F] OCH(2)CH(2)F substituent at the para-position of the C-1 phenyl ring, and a [(18)F] CH(2)CH(2)F substituent at the C-2 position of the olefinic bond. The [(11)C] and [(18)F] radiotracers are designed as potential radiopharmaceuticals to image cyclooxygenase-2 (COX-2) expression in any organ where COX-2 is upregulated. The COX-1/COX-2 inhibition data acquired suggest that compounds having a [(11)C] OMe or [(18)F] OCH(2)CH(2)F substituent at the para-position of the C-1 phenyl ring may be more suitable for imaging COX-2 expression in view of their ability to exclusively inhibit the COX-2 isozyme. (C) 2010 Elsevier Ltd. All rights reserved.
• Methylsulfonyl and Hydroxyl Substituents Induce<i>Z</i>-Stereocontrol in the McMurry Olefination Reaction
  作者：Edward E. Knaus、Md. Jashim Uddin、P. N. Rao

  DOI：10.1055/s-2004-829087

  日期：——

  Aryl ketones possessing methylsulfonyl and hydroxyl substituents, that induce stereocontrol, selectively afford Z-olefins using a Zn-TiCl4 catalyzed McMurry reaction.

  具有甲基磺酰基和羟基取代基的芳基酮，能够引导立体控制，在Zn-TiCl4催化的McMurry反应中选择性地生成Z-烯烃。