(E)-1-(naphthalen-2-yl)-5-phenylpent-2-en-1-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (E)-1-(naphthalen-2-yl)-5-phenylpent-2-en-1-one
• 英文别名: (E)-1-naphthalen-2-yl-5-phenylpent-2-en-1-one
• 化学式: C₂₁H₁₈O
• 分子量: 286.373
• InChiKey: PDMFNBZPLFJAFS-NTUHNPAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• 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：

  二氯甲烷 、 (E)-1-(naphthalen-2-yl)-5-phenylpent-2-en-1-one 在 bis(acetylacetonate)nickel(II) 、 4-(tert-Butyl)-2-(quinolin-2-yl)-4,5-dihydrooxazole 、 锌 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 以56%的产率得到naphthalen‐2‐yl(2‐phenethylcyclopentyl)methanone
  参考文献：
  名称：

  Catalytic Cyclooligomerization of Enones with Three Methylene Equivalents

  摘要：

  Cyclic structures are highly represented in organic molecules, motivating a wealth of catalytic methods targeting their synthesis. Among the various ring-forming processes, cyclooligomerization reactions possess several attractive features but require addressing a unique challenge associated with controlling ring-size selectivity. Here we describe the catalytic reductive cocyclooligomerization of an enone and three carbene equivalents to generate a cyclopentane, a process that constitutes a formal [2 + 1 + 1 + 1]-cycloaddition. The reaction is promoted by a (quinox)Ni catalyst and uses CH2Cl2/Zn as the C-1 component. Mechanistic studies are consistent with a metallacycle-based pathway, featuring sequential migratory insertions of multiple carbene equivalents to yield cycloalkanes larger than cyclopropanes.

  DOI：

  10.1021/jacs.8b08296
• 作为产物：
  描述：

  2-萘甲酸甲酯 在 正丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 为溶剂， 生成 (E)-1-(naphthalen-2-yl)-5-phenylpent-2-en-1-one
  参考文献：
  名称：

  GPR52拮抗剂降低亨廷顿病水平并改善亨廷顿舞蹈病相关表型

  摘要：

  GPR52是一种孤儿G蛋白偶联受体（GPCR），最近被认为是亨廷顿氏病（HD）（一种无法治愈的单基因神经退行性疾病）的潜在药物靶标。在这项研究中，我们发现GPR52的纹状体敲低可降低成年HdhQ140小鼠的mHTT水平，从而将GPR52确认为HD靶标。此外，通过结构-活性关系（SAR）研究，我们发现了一种高效且特异的GPR52拮抗剂Comp- 43，IC 50值为0.63μM 。进一步的研究表明，Comp- 43通过靶向GPR52降低mHTT水平，并促进了小鼠原代纹状体神经元的存活。此外，体内研究表明Comp- 43不仅降低了mHTT水平，而且还挽救了HdhQ140小鼠的HD相关表型。两者合计，我们的研究证实，抑制GPR52是HD治疗的一种有前途的策略，而GPR52拮抗剂Comp- 43可能充当进一步研究的先导化合物。

  DOI：

  10.1021/acs.jmedchem.0c01133

文献信息

• Direct Access to α,β-Unsaturated Ketones via Rh/MgCl₂-Mediated Acylation of Vinylsilanes
  作者：Xue-Zu Deng、Zi-Yan Chen、Yang Song、Fei Xue、Motoki Yamane、Yan-Ni Yue

  DOI：10.1021/acs.joc.1c01205

  日期：2021.9.17

  We report herein the facile and practical construction of α,β-unsaturated ketones via rhodium-catalyzed direct acylation of vinylsilanes with readily available and abundant carboxylic acids. This protocol features access to a diverse array of synthetically useful functionalities with moderate to excellent yields. More importantly, the late-stage functionalization of pharmaceuticals was also realized

  我们在此报告了通过铑催化的乙烯基硅烷与易得且丰富的羧酸的直接酰化来构建 α,β-不饱和酮的简便实用的结构。该协议的特点是可以访问各种综合有用的功能，并具有中等至出色的产量。更重要的是，药物的后期功能化也以合成有用的产率实现。
• METHOD OF ENANTIOSELECTIVE ADDITION TO ENONES
  申请人：UANG Biing-Jiun

  公开号：US20110282101A1

  公开（公告）日：2011-11-17

  The present invention relates to a method of enantioselective addition to enones, including: reacting R 3 (CH 2 ) p CH═CR 5 C(═O)Y(CH 2 ) q R 4 with R 6 ZnR 7 in the presence of a compound represented by the following formula (I) and a transition metal catalyst, in which Y, p, q, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and R 7 are defined the same as the specification. Accordingly, the present invention can perform asymmetric conjugate addition in high yields and enantioselectivity.

  本发明涉及一种对烯酮进行对映选择性加成的方法，包括：在存在以下式（I）所代表的化合物和过渡金属催化剂的情况下，将R3(CH2)pCH═CR5C(═O)Y(CH2)qR4与R6ZnR7反应，其中Y、p、q、R1、R2、R3、R4、R5、R6和R7的定义与规范相同。因此，本发明可以在高产率和对映选择性下进行不对称共轭加成。
• US8304581B2
  申请人：——

  公开号：US8304581B2

  公开（公告）日：2012-11-06
• Catalytic Cyclooligomerization of Enones with Three Methylene Equivalents
  作者：Conner M. Farley、You-Yun Zhou、Nishit Banka、Christopher Uyeda

  DOI：10.1021/jacs.8b08296

  日期：2018.10.10

  Cyclic structures are highly represented in organic molecules, motivating a wealth of catalytic methods targeting their synthesis. Among the various ring-forming processes, cyclooligomerization reactions possess several attractive features but require addressing a unique challenge associated with controlling ring-size selectivity. Here we describe the catalytic reductive cocyclooligomerization of an enone and three carbene equivalents to generate a cyclopentane, a process that constitutes a formal [2 + 1 + 1 + 1]-cycloaddition. The reaction is promoted by a (quinox)Ni catalyst and uses CH2Cl2/Zn as the C-1 component. Mechanistic studies are consistent with a metallacycle-based pathway, featuring sequential migratory insertions of multiple carbene equivalents to yield cycloalkanes larger than cyclopropanes.
• GPR52 Antagonist Reduces Huntingtin Levels and Ameliorates Huntington’s Disease-Related Phenotypes
  作者：Congcong Wang、Yu-Fang Zhang、Shimeng Guo、Quan Zhao、Yanping Zeng、Zhicheng Xie、Xin Xie、Boxun Lu、Youhong Hu

  DOI：10.1021/acs.jmedchem.0c01133

  日期：2021.1.28

  studies showed that Comp-43 reduces mHTT levels by targeting GPR52 and promotes survival of mouse primary striatal neurons. Moreover, in vivo study showed that Comp-43 not only reduces mHTT levels but also rescues HD-related phenotypes in HdhQ140 mice. Taken together, our study confirms that inhibition of GPR52 is a promising strategy for HD therapy, and the GPR52 antagonist Comp-43 might serve as a lead

  GPR52是一种孤儿G蛋白偶联受体（GPCR），最近被认为是亨廷顿氏病（HD）（一种无法治愈的单基因神经退行性疾病）的潜在药物靶标。在这项研究中，我们发现GPR52的纹状体敲低可降低成年HdhQ140小鼠的mHTT水平，从而将GPR52确认为HD靶标。此外，通过结构-活性关系（SAR）研究，我们发现了一种高效且特异的GPR52拮抗剂Comp- 43，IC 50值为0.63μM 。进一步的研究表明，Comp- 43通过靶向GPR52降低mHTT水平，并促进了小鼠原代纹状体神经元的存活。此外，体内研究表明Comp- 43不仅降低了mHTT水平，而且还挽救了HdhQ140小鼠的HD相关表型。两者合计，我们的研究证实，抑制GPR52是HD治疗的一种有前途的策略，而GPR52拮抗剂Comp- 43可能充当进一步研究的先导化合物。