3-dimethylamino-1(4-chloro-phenyl)-2-propen-1-one | 28587-05-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-dimethylamino-1(4-chloro-phenyl)-2-propen-1-one
• 英文别名: 1-(4-chlorophenyl)-3-(dimethylamino)prop-2-en-1-one；4'-Chloro-3-dimethylaminoacrylophenone
• CAS: 28587-05-5
• 化学式: C₁₁H₁₂ClNO
• mdl: MFCD00172116
• 分子量: 209.675
• InChiKey: TWBABRJLWCBTBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT

SDS

1-(4-氯苯基)-3-(二甲基氨基)-2-丙烯-1-酮MSDS英文版

反应信息

• 作为反应物：
  描述：

  3-dimethylamino-1(4-chloro-phenyl)-2-propen-1-one 在 三异丙氧基氯化钛 、 三乙酰氧基硼氢化钠 、 溶剂黄146 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 4-(4-chlorophenyl)-N-(piperidin-4-yl)pyrimidin-2-amine
  参考文献：
  名称：

  Discovery of piperidinyl aminopyrimidine derivatives as IKK-2 inhibitors

  摘要：

  A serine-threonine kinase IKK-2 plays an important role in activation of NF-kappa B through phosphorylation of the inhibitor of NF-kappa B (I kappa B). As NF-kappa B is a major transcription factor that regulates genes responsible for cell proliferation and inflammation, development of selective IKK-2 inhibitors has been an important area of anti-inflammatory and anti-cancer research. In this study, to obtain active and selective IKK-2 inhibitors, various substituents were introduced to a piperidinyl aminopyrimidine core structure. The structure-activity relationship study indicated that hydrogen, methanesulfonyl, and aminosulfonyl groups substituted at the piperidinylamino functionality provide high inhibitory activity against IKK-2. Also, morpholinosulfonyl and piperazinosulfonyl group substituted at the aromatic ring attached to the aminopyrimidine core significantly increased the inhibitory activity of the resulting derivatives. In particular, compound 17 with the aromatic piperazinosulfonyl substituent showed the most potent (IC50 = 1.30 mu M) and selective (over other kinases such as p38 alpha, p38 beta, JNK1, JNK2, JNK3, and IKK-1) inhibitory activity against IKK-2. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.044
• 作为产物：
  描述：

  对氯苯乙酮 以 N,N-二甲基甲酰胺二乙基缩醛 为溶剂， 生成 3-dimethylamino-1(4-chloro-phenyl)-2-propen-1-one
  参考文献：
  名称：

  Pyrimidineamine derivatives and processes for the preparation thereof

  摘要：

  描述了公式（I）的N-苯基-2-嘧啶胺衍生物，其中取代基如权利要求1所定义。这些化合物可以用于治疗肿瘤疾病。 ##STR1##

  公开号：

  US05612340A1

文献信息

• A copper-catalyzed three component reaction of aryl acetylene, sulfonyl azide and enaminone to form iminolactone <i>via</i> 6π electrocyclization
  作者：Jiarui Sun、Xiangsheng Cheng、John Kamanda Mansaray、Weihong Fei、Jieping Wan、Weijun Yao

  DOI：10.1039/c8cc06868b

  日期：——

  sulfonyl azide to construct iminolactone via a cascade process involving copper-catalyzed alkyne–azide cycloaddition (CuAAC), Michael addition of metalated ketenimine followed by elimination and 6π electrocyclization.

  我们开发了一种铜催化的芳基乙炔，烯胺酮和磺酰叠氮化物的三组分反应，通过级联工艺来构建亚氨基内酯，该工艺涉及铜催化的炔炔叠氮化物环加成反应（CuAAC），金属加成的酮亚胺的迈克尔加成反应，然后消除和6π电环化。
• Direct Synthesis of 2,3-Diaroyl Quinolines and Pyridazino[4,5-<i>b</i>]quinolines via an I₂-Promoted One-Pot Multicomponent Reaction
  作者：Peng Zhao、Xia Wu、You Zhou、Xiao Geng、Can Wang、Yan-dong Wu、An-Xin Wu

  DOI：10.1021/acs.orglett.9b00685

  日期：2019.4.19

  The first synthesis of 2,3-diaroyl quinolines via a formal [3 + 2 + 1] cycloaddition of enaminones, aryl methyl ketones, and aryl amines is disclosed. This reaction efficiently affords a 1,4-dicarbonyl scaffold, which is a useful building block for constructing complex fused heterocycles. Furthermore, the 1,4-dicarbonyl scaffold has been used directly to prepare pyridazino[4,5-b]quinoline skeletons

  公开了通过烯胺酮，芳基甲基酮和芳基胺的正式[3 + 2 + 1]环加成的2，3-二酰基酰基喹啉的首次合成。该反应有效地提供了1，4-二羰基支架，这是用于构建复杂的稠合杂环的有用的构建基。此外，已将1，4-二羰基支架直接用于一锅制备哒嗪并[4,5- b ]喹啉骨架。
• Iodine-mediated synthesis of sulfur-bridged enaminones and chromones via double C(sp²)–H thiolation
  作者：Yong Gao、Li Wei、Yunyun Liu、Jie-Ping Wan

  DOI：10.1039/c7ob00619e

  日期：——

  reactions of various enaminones with elemental sulfur giving rise to both sulfur-bridged enaminones and chromones have been realized via iodine promotion. All products were furnished by means of double C(sp2)–H bond thiolation without using any metal catalyst or sensitive oxidant, providing a simple and efficient protocol for the synthesis of diverse sulfur derivatives of enaminones.

  通过碘的促进已经实现了各种烯胺酮与元素硫的反应，其同时引起硫桥联的烯胺酮和色酮。所有产品均通过双C（sp 2）-H键硫醇化而无需使用任何金属催化剂或敏感氧化剂即可提供，为合成烯胺酮的多种硫衍生物提供了简单有效的方案。
• 3-Aminopyrazolo[4,3-<i>c</i>]pyridine-4,6-dione as a precursor for novel pyrazolo[4,5,1-ij][1,6]naphthyridines and pyrido[4’,3’:3,4]pyrazolo[1,5-<i>a</i>]pyrimidines
  作者：Nadia H. Metwally、Emad A. Deeb

  DOI：10.1080/00397911.2018.1457162

  日期：2018.7.3

  aryldiazonium chlorides, chalcones and enaminones to afford regioselectively the novel pyrazolo[4,3-c]pyridine derivatives 4a-c, pyrazolo[4,5,1-ij][1,6] naphthyridines 9a-d and pyrido[4’,3':3,4]pyrazlo[1,5-a]pyrimidines 19a-i. The structure of all the newly synthesized compounds was assigned from elemental analysis and spectral data. Also, the mechanistic aspects for the formation of the newly synthesized

  摘要 合成了多功能的 3-氨基吡唑并 [4,3-c] 吡啶-4,6-二酮 (2)，并使其与醛、芳基重氮氯化物、查耳酮和烯胺酮反应，以区域选择性地提供新型吡唑并 [4,3- c]吡啶衍生物4a-c，吡唑并[4,5,1-ij][1,6]萘啶9a-d和吡啶并[4',3':3,4]吡唑并[1,5-a]嘧啶19a -一世。所有新合成的化合物的结构都是根据元素分析和光谱数据确定的。此外，还讨论了形成新合成化合物的机制方面。图形概要
• An expedient synthesis of highly functionalized 1,3-dienes by employing cyclopropenes as <i>C</i>₄ units
  作者：Chengzhou Jiang、Jiamin Wu、Jiabin Han、Kai Chen、Yang Qian、Zhengyu Zhang、Yaojia Jiang

  DOI：10.1039/d1cc01254a

  日期：——

  chosen as standard C4 units of 1,3-diene precursors. The reactions are believed to undergo a unique cutting and insertion process, involving a CC bond cleavage of the enaminone and insertion of a new C(sp2) source with the formation of two C–C single bonds. A broad range of substrates can be used to synthesize the corresponding 1,3-dienes under very mild reaction conditions, including low catalyst-loading

  已经描述了通过在铑催化剂的存在下用环丙烯裂解烯胺酮的C C键来合成二羰基官能化的1，3-二烯的有效方法。明智地选择乙酸酯取代的环丙烯作为1，3-二烯前体的标准C 4单元。据信，这些反应经历了独特的切割和插入过程，包括烯胺酮的C C键裂解和插入新的C（sp 2）源并形成两个C C单键。在非常温和的反应条件下，包括低催化剂负载，环境温度和中性反应溶剂，可以使用各种各样的底物来合成相应的1,3-二烯。