1-bromo-4-(4-chlorophenyl)but-3-en-2-one | 1392239-32-5

• 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: 1-bromo-4-(4-chlorophenyl)but-3-en-2-one
• 英文别名: 1-Bromo-4-(4-chlorophenyl)but-3-en-2-one
• CAS: 1392239-32-5
• 化学式: C₁₀H₈BrClO
• 分子量: 259.53
• InChiKey: YUJKQOZICDOQAN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-bromo-4-(4-chlorophenyl)but-3-en-2-one 在 四丁基硫酸氢铵 、 potassium carbonate 、 DL-脯氨酸 作用下， 以 二氯甲烷 、 水 、 二甲基亚砜 为溶剂， 生成
  参考文献：
  名称：

  3-取代的2 H -1,4-苯并恶嗪的直接有机催化不对称曼尼希加成：获得四取代的碳立体中心

  摘要：

  Abstract3‐Substituted‐2H‐1,4‐benzoxazines undergo a highly enantioselective direct Mannich reaction with acetone in the presence of an L‐proline catalyst at room temperature. The corresponding N‐heterocycles with α‐tetrasubstituted carbon stereocenters were obtained in good yields (48–92%) and excellent enantioselectivity (up to >99% ee). Furthermore, a novel modification involving the diastereoselective reduction of the Mannich adduct was carried out leading to the formation of a 1,3‐amino alcohol with a chiral tetrasubstituted carbon stereocenter in high yield.magnified image

  DOI：

  10.1002/adsc.201300654
• 作为产物：
  描述：

  4-氯苯亚甲基丙酮 在 pyrrolidone hydrotribromide 作用下， 以 四氢呋喃 为溶剂， 生成 1-bromo-4-(4-chlorophenyl)but-3-en-2-one
  参考文献：
  名称：

  磷阳离子辅助 Rh(III) 催化的烯基 C-H 活化合成 3,4,5-三取代酚

  摘要：

  通过Rh( III ) 催化的鏻阳离子与内部炔烃的偶联，实现了构建各种 3,4,5-三取代苯酚衍生物的有效方法。该协议显示出良好的底物兼容性，因为一系列结构和电子不同的磷化合物有效反应，产率高达 87%。

  DOI：

  10.1039/d3cc00017f

文献信息

• Synthesis of 2-alkenyl-3-hydroxyquinolin-4(1 H )-ones as promising antimicrobial and fluorescent agents
  作者：Radim Horák、Lubomír Kvapil、Kamil Motyka、Ludmila Slaninová、Martin Grepl、Kamil Kořistek、Miroslav Urbášek、Pavel Hradil、Miroslav Soural

  DOI：10.1016/j.tet.2017.12.010

  日期：2018.1

  2-Alkenyl-3-hydroxyquinolin-4(1H)-ones were prepared by the rearrangement of anthranilic acid esters synthesized by two alternative methods. The prepared derivatives were screened for their antimicrobial activities against representative Gram-positive and Gram-negative bacteria, displaying notable minimum inhibitory concentration values against specific strains. The emission spectra of the target quinolines

  通过重排由两种替代方法合成的邻氨基苯甲酸酯制备2-烯基-3-羟基喹啉-4（1 H）-one。筛选制备的衍生物对代表性革兰氏阳性和革兰氏阴性细菌的抗菌活性，显示出对特定菌株的显着最小抑菌浓度值。目标喹啉的发射光谱显示出两个分离良好的发射带，并且在相对较高的值下检测到所选化合物的最大激发波长。
• Synthesis and antiproliferativeactivity of new vinca alkaloids containing an α,β-unsaturated aromatic side chain
  作者：Quoc Anh Ngo、Le Anh Nguyen、Ngoc Binh Vo、Thuy Hang Nguyen、Fanny Roussi、The Hung Nguyen、Van Tuyen Nguyen

  DOI：10.1016/j.bmcl.2015.10.040

  日期：2015.12

  A new series of vinca-alkaloids derivatives containing various alpha,beta-unsaturated aromatic side chains was synthesized. Four new vinca-alkaloids derivatives showed selective cytotoxicities against KB tumor cell lines with IC50 value below 0.1 mu M, thus comparable with vinblastine. (C) 2015 Elsevier Ltd. All rights reserved.
• Direct Organocatalytic Asymmetric Mannich Addition of 3-Substituted-2<i>H</i>-1,4-Benzoxazines: Access to Tetrasubstituted Carbon Stereocenters
  作者：You-Qing Wang、Yongna Zhang、Kun Pan、Junxiong You、Jin Zhao

  DOI：10.1002/adsc.201300654

  日期：2013.11.25

  Abstract3‐Substituted‐2H‐1,4‐benzoxazines undergo a highly enantioselective direct Mannich reaction with acetone in the presence of an L‐proline catalyst at room temperature. The corresponding N‐heterocycles with α‐tetrasubstituted carbon stereocenters were obtained in good yields (48–92%) and excellent enantioselectivity (up to >99% ee). Furthermore, a novel modification involving the diastereoselective reduction of the Mannich adduct was carried out leading to the formation of a 1,3‐amino alcohol with a chiral tetrasubstituted carbon stereocenter in high yield.magnified image
• Synthesis of 3,4,5-trisubstituted phenols <i>via</i> Rh(<scp>iii</scp>)-catalyzed alkenyl C–H activation assisted by phosphonium cations
  作者：Yan Mao、Wenxi Chen、Changchang Li、Lin Miao、Yanfei Lin、Fei Ling、Zhangpei Chen、Jinzhong Yao

  DOI：10.1039/d3cc00017f

  日期：——

  construction of various 3,4,5-trisubstituted phenol derivatives has been achieved via the Rh(III)-catalyzed coupling of phosphonium cations with internal alkynes. This protocol shows good substrate compatibility, as an array of structurally and electronically diverse phosphonium compounds react efficiently with up to 87% yield.

  通过Rh( III ) 催化的鏻阳离子与内部炔烃的偶联，实现了构建各种 3,4,5-三取代苯酚衍生物的有效方法。该协议显示出良好的底物兼容性，因为一系列结构和电子不同的磷化合物有效反应，产率高达 87%。