4′-(dimethylamino)-5,6-dihydro-[1,1′-biphenyl]-3(4H)-one | 1096155-81-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4′-(dimethylamino)-5,6-dihydro-[1,1′-biphenyl]-3(4H)-one
• 英文别名: 4'-(dimethylamino)-5,6-dihydro-[1,1'-biphenyl]-3(4H)-one；3-[4-(dimethylamino)phenyl]cyclohex-2-en-1-one；3-(4-(dimethylamino)phenyl)cyclohex-2-enone
• CAS: 1096155-81-5
• 化学式: C₁₄H₁₇NO
• 分子量: 215.295
• InChiKey: FKTIAQASAZFTGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4′-(dimethylamino)-5,6-dihydro-[1,1′-biphenyl]-3(4H)-one 、 4-甲苯硼酸 在 2,2'-联吡啶 、 palladium(II) trifluoroacetate 、 sodium 2,2,2-trifluoroacetate 作用下， 以 水 为溶剂， 反应 24.0h， 生成 3-(4-(dimethylamino)phenyl)-3-(p-tolyl)cyclohexan-1-one
  参考文献：
  名称：

  对映选择性，钯催化的芳基硼酸共轭加成反应生成双苄基四元立体中心。

  摘要：

  我们报道了对羟基苯甲酸对β-芳基，β，β-二取代的烯酮的对映选择性，钯催化的共轭加成反应，以生成含有双苄基季立体中心的酮。由三氟乙酸钯和（S）-4-叔丁基-2-（2-吡啶基）恶唑啉配体（（S）-t- BuPyOx）生成的催化剂促进多种芳基硼酸向各种β的共轭加成反应-芳基，β，β-二取代的烯酮。反复添加芳基硼酸以使不希望的原去硼烷化路径减至最少导致有效地形成相应的含有双苄基季立体中心的酮，产率高达92％，对映选择性高达93％。

  DOI：

  10.1021/acs.orglett.7b01825
• 作为产物：
  描述：

  2-环己烯-1-酮 、 4-碘-N,N-二甲基苯胺 在 N-(4-carbethoxyphenyl)urea 、 palladium diacetate 、 potassium carbonate 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 为溶剂， 反应 16.0h， 以76%的产率得到4′-(dimethylamino)-5,6-dihydro-[1,1′-biphenyl]-3(4H)-one
  参考文献：
  名称：

  Selective reactivity of electron-rich aryl iodides in the Heck arylation of disubstituted alkenes catalyzed by palladium–arylurea complexes

  摘要：

  A catalyst consisting of 1 mol % of the 1:2 complex of Pd(OAc)(2) with N-(4-carbethoxyphenyl)urea promotes the Heck arylation of 2- or 3-substituted, conjugated esters, nitriles, aldehydes, and ketones (an uncharacteristically broad range of substrates), but only with electron-rich aryl iodides (an uncharacteristically narrow range of halides). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.09.019

文献信息

• Oxidative Heck Reaction as a Tool for Para-selective Olefination of Aniline: A DFT Supported Mechanism
  作者：Firouz Matloubi Moghaddam、Raheleh Pourkaveh、Ashkan Karimi

  DOI：10.1021/acs.joc.7b01570

  日期：2017.10.6

  This study describes the first para-selective palladium-catalyzed alkenylation of tertiary amines. This regioselective C–H activation was conducted without any chelation moieties. A series of olefins were reacted under mild reaction conditions at 60 °C, and the corresponding products were obtained in good yields with high selectivity.

  这项研究描述了叔胺的第一个对位选择性钯催化的烯基化反应。这种区域选择性的C–H激活没有任何螯合部分。在温和的反应条件下，于60°C下反应，使一系列烯烃反应，并以高收率和高选择性获得了相应的产物。
• Structurally Simple Dipolar Organic Dyes Featuring 1,3-Cyclohexadiene Conjugated Unit for Dye-Sensitized Solar Cells
  作者：Kuan-Fu Chen、Ying-Chan Hsu、Qiongyou Wu、Ming-Chang P. Yeh、Shih-Sheng Sun

  DOI：10.1021/ol802630x

  日期：2009.1.15

  A series of structurally simple dipolar light-harvesting organic dyes featuring 1,3-cyclohexadiene in the aromatic pi framework for dye-sensitized solar cells has been synthesized and characterized. The highest conversion efficiency of the DSSCs based on these dyes can reach up to 4.4%.
• Selective reactivity of electron-rich aryl iodides in the Heck arylation of disubstituted alkenes catalyzed by palladium–arylurea complexes
  作者：Matthew R. Smith、Young Jin Jang、Jung Yun Kim、Marco A. Ciufolini

  DOI：10.1016/j.tet.2013.09.019

  日期：2013.11

  A catalyst consisting of 1 mol % of the 1:2 complex of Pd(OAc)(2) with N-(4-carbethoxyphenyl)urea promotes the Heck arylation of 2- or 3-substituted, conjugated esters, nitriles, aldehydes, and ketones (an uncharacteristically broad range of substrates), but only with electron-rich aryl iodides (an uncharacteristically narrow range of halides). (C) 2013 Elsevier Ltd. All rights reserved.
• Enantioselective, Palladium-Catalyzed Conjugate Additions of Arylboronic Acids to Form Bis-benzylic Quaternary Stereocenters
  作者：Abhishek A. Kadam、Arkady Ellern、Levi M. Stanley

  DOI：10.1021/acs.orglett.7b01825

  日期：2017.8.4

  We report enantioselective, palladium-catalyzed conjugate additions of arylboronic acids to β-aryl, β,β-disubstituted enones to generate ketones containing bis-benzylic quaternary stereocenters. A catalyst generated from palladium trifluoroacetate and (S)-4-tert-butyl-2-(2-pyridyl)oxazoline ligand ((S)-t-BuPyOx) promotes conjugate additions of a wide range of arylboronic acids to a variety of β-aryl

  我们报道了对羟基苯甲酸对β-芳基，β，β-二取代的烯酮的对映选择性，钯催化的共轭加成反应，以生成含有双苄基季立体中心的酮。由三氟乙酸钯和（S）-4-叔丁基-2-（2-吡啶基）恶唑啉配体（（S）-t- BuPyOx）生成的催化剂促进多种芳基硼酸向各种β的共轭加成反应-芳基，β，β-二取代的烯酮。反复添加芳基硼酸以使不希望的原去硼烷化路径减至最少导致有效地形成相应的含有双苄基季立体中心的酮，产率高达92％，对映选择性高达93％。