3-(pyridin-3-yl)acetophenone | 171092-38-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(pyridin-3-yl)acetophenone
• 英文别名: 1-(3-(pyridin-3-yl)phenyl)ethanone；1-[3-(3-pyridinyl)phenyl]ethanone；1-[3-(3-pyridyl)phenyl]ethanone；3-(3-acetylphenyl)pyridine；1-(3-pyridin-3-ylphenyl)ethanone
• CAS: 171092-38-9
• 化学式: C₁₃H₁₁NO
• 分子量: 197.236
• InChiKey: UDAUYQQCKXJZEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(Ethylamino)ethanethioamide 、 3-(pyridin-3-yl)acetophenone 在 氨 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以17 mg的产率得到1-ethyl-2-methyl-2-(3-(pyridin-3-yl)phenyl)-2,5-dihydro-1H-imidazol-4-amine
  参考文献：
  名称：

  Core Refinement toward Permeable β-Secretase (BACE-1) Inhibitors with Low hERG Activity

  摘要：

  By use of iterative design aided by predictive models for target affinity, brain permeability, and hERG activity, novel and diverse compounds based on cyclic amidine and guanidine cores were synthesized with the goal of finding BACE-1 inhibitors as a treatment for Alzheimer's disease. Since synthesis feasibility had low priority in the design of the cores, an extensive synthesis effort was needed to make the relevant compounds. Syntheses of these compounds are reported, together with physicochemical properties and structure-activity relationships based on in vitro data. Four crystal structures of diverse amidines binding in the active site are deposited and discussed. Inhibitors of BACE-1 with 3 mu M to 32 nM potencies in cells are shown, together with data on in vivo brain exposure levels for four compounds. The results presented show the importance of the core structure for the profile of the final compounds.

  DOI：

  10.1021/jm3011349
• 作为产物：
  描述：

  3-氯吡啶 、 3-乙酰基苯硼酸 在 palladium diacetate 、 potassium fluoride 、 2-(二叔丁基膦)联苯 作用下， 以 四氢呋喃 为溶剂， 反应 9.0h， 以94%的产率得到3-(pyridin-3-yl)acetophenone
  参考文献：
  名称：

  用于 Suzuki 偶联反应的高活性钯催化剂

  摘要：

  乙酸钯和邻（二叔丁基膦）联苯 (4) 的混合物催化芳基溴和芳基氯与 0.5-1.0 mol% Pd 的室温 Suzuki 偶联。使用邻（二环己基膦基）联苯 (2) 允许在低催化剂负载（0.000001-0.02 mol% Pd）下进行 Suzuki 偶联。该工艺可以容忍广泛的官能团和底物组合，包括使用空间位阻底物。这是迄今为止已报道的在反应温度、转换数和空间耐受性方面最活跃的催化剂体系。

  DOI：

  10.1021/ja992130h

文献信息

• Ligands for metals and improved metal-catalyzed processes based thereon
  申请人：Massachusetts Institute of Technology

  公开号：US06307087B1

  公开（公告）日：2001-10-23

  One aspect of the present invention relates to novel ligands for transition metals. A second aspect of the present invention relates to the use of catalysts comprising these ligands in transition metal-catalyzed carbon-heteroatom and carbon-carbon bond-forming reactions. The subject methods provide improvements in many features of the transition metal-catalyzed reactions, including the range of suitable substrates, reaction conditions, and efficiency.

  本发明的一个方面涉及用于过渡金属的新颖配体。本发明的第二个方面涉及在过渡金属催化的碳-杂原子和碳-碳键形成反应中使用含有这些配体的催化剂。本方法在许多过渡金属催化反应的特征上提供了改进，包括适宜的底物范围、反应条件和效率。
• Efficient Diphosphane-Based Catalyst for the Palladium-Catalyzed Suzuki Cross-Coupling Reaction of 3-Pyridylboronic Acids
  作者：Xing-Li Fu、Lei-Lei Wu、Hai-Yan Fu、Hua Chen、Rui-Xiang Li

  DOI：10.1002/ejoc.200900038

  日期：2009.5

  4′-bis(diphenylphosphanyl)-3,3′-bipyridine (P-Phos) has been developed for the Suzuki cross-coupling reaction of pyridylboronic acid with a variety of aryl halides in good to excellent yields, even in the presence of hindered and functional groups. In addition, P-Phos also exhibited high activity in the palladium-catalyzed Suzuki reaction of 2,6-dimethoxypyridylboronic acid in excellent yields with a fast

  已经为铃木交叉偶联开发了一种源自 PdCl2 和 2,2',6,6'-四甲氧基-4,4'-双（二苯基膦酰基）-3,3'-联吡啶（P-Phos）的高活性催化剂体系吡啶基硼酸与各种芳基卤化物的反应，即使在受阻和官能团存在的情况下，也能以良好到极好的收率进行反应。此外，P-Phos 在钯催化的 2,6-二甲氧基吡啶基硼酸的 Suzuki 反应中也表现出高活性，产率高，速度快。还讨论了 P-Phos-钯配合物对这种交叉偶联反应的空间和电子效应。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• Kinetic Resolution of 1-Biaryl- and 1-(Pyridylphenyl)alkan-1-ols Catalysed by the Lipase B from<i>Candida antarctica</i>
  作者：Robert Kourist、Javier González-Sabín、Ramón Liz、Francisca Rebolledo

  DOI：10.1002/adsc.200404330

  日期：2005.4

  enantioselective (E>200) transesterification of some 1-biaryl-2-yl-, -3-yl-, and -4-ylethanols and -propan-1-ols, as well as 1-(o-, m-, and p-pyridylphenyl)ethanols, 6, with vinyl acetate, Kazlauskas' rule being obeyed in all cases. meta and para-Substituted substrates were transformed within several hours (conversion degree ranging from 23–50%), reaction rates for propan-1-ol derivatives being slower than

  南极假丝酵母的脂肪酶B （CAL-B）催化一些1-联芳基-2-基-，-3-基和-4-基乙醇和-丙-1-醇的高度对映选择性（E > 200）酯交换，以及1-（o-，m-和对-吡啶基苯基）乙醇6含乙酸乙烯酯，在所有情况下均应遵守Kazlauskas规则。间位和对位取代的底物在数小时内转化（转化率范围为23-50％），丙-1-醇衍生物的反应速率比乙醇衍生物的反应速率慢。邻位酯交换-取代的醇用了几天，并伴有化学酶促副反应：形成了另一种由半缩醛衍生的乙酸酯，其在6和乙醛之间是由乙酸乙烯酯形成的。在乙酸异丙烯酯作为酰基供体的情况下，该副反应被抑制，酯交换反应的转化度在十天后为20-40％（E > 200）。还证明了（R）-6p作为配体在将二乙基锌不对称加成到苯甲醛中的有用性。
• Ligands for Metals and Improved Metal-Catalyzed Processes Based Thereon
  申请人：Buchwald L. Stephen

  公开号：US20080033171A1

  公开（公告）日：2008-02-07

  One aspect of the present invention relates to novel ligands for transition metals. A second aspect of the present invention relates to the use of catalysts comprising these ligands in transition metal-catalyzed carbon-heteroatom and carbon-carbon bond-forming reactions. The subject methods provide improvements in many features of the transition metal-catalyzed reactions, including the range of suitable substrates, reaction conditions, and efficiency.

  本发明的一个方面涉及新型过渡金属配体。本发明的第二个方面涉及在过渡金属催化的碳-杂原子和碳-碳键形成反应中使用包含这些配体的催化剂。该方法提供了许多过渡金属催化反应的改进特性，包括适合底物的范围，反应条件和效率。
• INHIBITORS OF MYOCARDIN-RELATED TRANSCRIPTION FACTOR AND SERUM RESPONSE FACTOR (MRTF/SRF)-MEDIATED GENE TRANSCRIPTION AND METHODS FOR USE OF THE SAME
  申请人：THE REGENTS OF THE UNIVERSITY OF MICHIGAN

  公开号：US20160145251A1

  公开（公告）日：2016-05-26

  Disclosed herein are inhibitors of gene transcription mediated by myocardin-related transcription factor and serum response factor, or both myocardin-related transcription factor and serum response factor (“MRTF/SRF”), and methods for their use in treating or preventing cancer and fibrosis. In particular, disclosed herein are compounds of Formula (I) and Formula (II), and pharmaceutically acceptable salts thereof: wherein the substituents are as described.

  本文披露了抑制由肌动蛋白相关转录因子和血清反应因子或肌动蛋白相关转录因子和血清反应因子（“MRTF / SRF”）介导的基因转录的抑制剂，以及它们在治疗或预防癌症和纤维化方面的使用方法。特别地，本文披露了公式（I）和公式（II）的化合物及其药学上可接受的盐：其中取代基如所述。