5-(4-methoxyphenyl)pentanoyl chloride | 61875-52-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-(4-methoxyphenyl)pentanoyl chloride
• 英文别名: 5-(4-methoxy-phenyl)-valeryl chloride；5-(4-Methoxy-phenyl)-valeriansaeure-chlorid
• CAS: 61875-52-3
• 化学式: C₁₂H₁₅ClO₂
• 分子量: 226.703
• InChiKey: VIYFCMLSFZMFEL-UHFFFAOYSA-N

物化性质

• 沸点：
  328.2±25.0 °C(Predicted)
• 密度：
  1.109±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-(4-methoxyphenyl)pentanoyl chloride 在 盐酸 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 为溶剂， 反应 8.5h， 生成 1-[5-(4-甲氧基-苯基)-戊基]-1,3-二氢-咪唑-2-硫酮
  参考文献：
  名称：

  Multisubstrate inhibitors of dopamine .beta.-hydroxylase. 1. Some 1-phenyl and 1-phenyl-bridged derivatives of imidazole-2-thione

  摘要：

  The synthesis and characterization of some 1-(phenylalkyl)imidazole-2-thiones as a novel class of "multisubstrate" inhibitors of dopamine beta-hydroxylase (DBH) are described. These inhibitors incorporate structural features that resemble both tyramine and oxygen substrates, and as evidenced by steady-state kinetics, they appear to bind both the phenethylamine binding site and the active site copper atom(s) in DBH. A series of structural congeners that incorporate different bridging chain lengths between the phenyl ring (dopamine mimic) and the imidazole-2-thione group (oxygen mimic) define the optimum distance for inhibitory potency and the likely intersite distance in the DBH active site. Additional bridging analogues were prepared to determine the active site bulk tolerance and the effects of heteroatom replacement.

  DOI：

  10.1021/jm00162a008
• 作为产物：
  描述：

  ethyl 5-(4-methoxyphenyl)pentanoate 在 草酰氯 、 N,N-二甲基甲酰胺 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 14.0h， 生成 5-(4-methoxyphenyl)pentanoyl chloride
  参考文献：
  名称：

  GVIA 钙非依赖性磷脂酶 A2 的新型强效选择性多氟烷基酮抑制剂

  摘要：

  VIA 组钙非依赖性磷脂酶 A 2 (GVIA iPLA 2 ) 最近已成为重要的药物靶点。选择性和有效的 GVIA iPLA 2抑制剂可用于研究其在各种神经系统疾病中的作用。在目前的工作中，我们探讨了在先前报道的强效 GVIA iPLA 2抑制剂中引入取代基的重要性。1,1,1,2,2-五氟-7-(4-甲氧基苯基)庚烷-3-one (GK187) 是有史以来报告的最有效和选择性的 GVIA iPLA 2抑制剂，其X I (50) 值为 0.0001，并且对 GIVA cPLA 2或 GV sPLA 2没有显着抑制作用. 我们还比较了两种二氟甲基酮对 GVIA iPLA 2、GIVA cPLA 2和 GV sPLA 2的抑制作用。

  DOI：

  10.1016/j.bmc.2013.07.010

文献信息

• Discovery of Cytochrome P450 4F11 Activated Inhibitors of Stearoyl Coenzyme A Desaturase
  作者：Sarah E. Winterton、Emanuela Capota、Xiaoyu Wang、Hong Chen、Prema L. Mallipeddi、Noelle S. Williams、Bruce A. Posner、Deepak Nijhawan、Joseph M. Ready

  DOI：10.1021/acs.jmedchem.8b00052

  日期：2018.6.28

  Stearoyl-CoA desaturase (SCD) catalyzes the first step in the conversion of saturated fatty acids to unsaturated fatty acids. Unsaturated fatty acids are required for membrane integrity and for cell proliferation. For these reasons, inhibitors of SCD represent potential treatments for cancer. However, systemically active SCD inhibitors result in skin toxicity, which presents an obstacle to their development

  硬脂酰辅酶A去饱和酶（SCD）催化饱和脂肪酸向不饱和脂肪酸转化的第一步。膜完整性和细胞增殖需要不饱和脂肪酸。由于这些原因，SCD抑制剂代表了潜在的癌症治疗方法。但是，具有内在活性的SCD抑制剂会导致皮肤毒性，这对它们的发展构成了障碍。我们最近描述了一系列草酸二酰胺，它们通过CYP4F11介导的代谢转化为癌症子集内的活性SCD抑制剂。在本文中，我们描述了草酸二酰胺和相关N-酰基脲的优化，以及与代谢活化和SCD抑制有关的结构-活性关系的分析。
• A Visible Light Driven Nickel Carbonylation Catalyst: The Synthesis of Acid Chlorides from Alkyl Halides
  作者：Kristian El Chami、Yi Liu、Mohammed A. Belahouane、Yiyang Ma、Pierre‐Louis Lagueux‐Tremblay、Bruce A. Arndtsen

  DOI：10.1002/anie.202213297

  日期：2023.3

  A visible light driven nickel carbonylation catalyst has been develop. This offers a method for carbonylative coupling reactions with an earth abundant metal at ambient temperature for the conversion of alkyl halides into synthetically versatile acid chlorides. The acid chlorides can then be transformed into an array of challenging ester, thioester and amide products.

  已经开发出可见光驱动的镍羰基化催化剂。这提供了一种在环境温度下与地球上丰富的金属进行羰基化偶联反应的方法，用于将卤代烷转化为合成用途广泛的酰氯。然后可以将酰氯转化为一系列具有挑战性的酯、硫酯和酰胺产品。
• BENZOTHIAZIN-3-ONE COMPOUND AND INTERMEDIATE THEREFOR
  申请人：Dainippon Sumitomo Pharma Co., Ltd.

  公开号：EP1726587B1

  公开（公告）日：2010-09-01
• Synthesis and Pharmacological Characterization of Novel 6-Fluorochroman Derivatives as Potential 5-HT_1A Receptor Antagonists
  作者：Tomoyuki Yasunaga、Takenori Kimura、Ryo Naito、Toru Kontani、Fumikazu Wanibuchi、Hiroshi Yamashita、Tamako Nomura、Shin-ichi Tsukamoto、Tokio Yamaguchi、Toshiyasu Mase

  DOI：10.1021/jm9707840

  日期：1998.7.1

  A series of novel 6-fluorochroman derivatives was prepared and evaluated as antagonists for the 5-HT1A receptor. N-2- [[(6-Fluorochroman-8-yl)oxy]ethyl]-4-(4-methoxyphenyl)butylamine (3; J. Med. Chem. 1997, 40, 1252-1257) was chosen as a lead, and structural modifications were done on the aliphatic portion of the chroman ring, the tether linking the middle amine and the terminal aromatic ring, the aromatic ring, and lastly the amine. Radioligand binding assays proved that the majority of the novel compounds behaved as good to excellent ligands at the 5-HT1A receptor, some of which were selective with respect to alpha(1)-adrenergic and D-2-dopaminergic receptors. The antagonist activity of the compounds was assessed in the forskolin-stimulated adenylate cyclase assays in CHO cells expressing the human 5-HT1A receptors. Among the modifications attempted, introduction of an oxo or an optically active hydroxy moiety at the chroman C-4 position was effective in ameliorating the receptor selectivity. Six analogues were selected through the in vitro screeds and further evaluated for their in vivo activities. A 4-oxochroman derivative (31n), having a terminal 1,3-benzodioxole ring, demonstrated antagonist activities toward 8-OH-DPAT-induced behavioral and electrophysiological responses in rats.
• The elasticity of the exine
  作者：John Rowley、John Skvarla

  DOI：10.1080/00173130150503759

  日期：2000.1

  We pressed pollen grain exines of ten genera with sizes ranging from about 20 to over 100 mu m in diameter past a piston in a close fitting cylinder. The clearance between piston and cylinder was about 20 mu m. Except for exines of Betula all the other pollen types were at least twice the clearance diameter and could be expected to be greatly deformed, crushed or fractured. Cracks were evident with the light microscope in some grains and a few were clearly deformed but most appeared intact, even exines of Zea mays at a diameter of 100-110 mu m. With scanning electron microscopy cracks were apparent in most of the large grains (Zea, Lilium, Pinus, Crinum and Epilobium) but not in the smaller grains (Betula, Ephedra, Tulipa, Fagus and Typha). We also found many exines within exines. In some cases, e.g., Lilium, the exines entered through apertures but in other grains such as Zea and Pinus, exines came in through cracks which had opened during acetolysis or centrifugation, then closed so tightly that the cracks were difficult to see with light microscopy. This opening and closing of cracks in exines means that the pollen grain exine is very flexible and resilient and capable of withstanding shock without permanent deformation. To regain their original form the exine components that were severely cracked, ruptured or partly separated must spring back together like the partly separated halves of a tennis ball.