2-(p-Tolyl)-vinyl-cyclopropylketon | 56105-34-1

• 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: 2-(p-Tolyl)-vinyl-cyclopropylketon
• 英文别名: 1-Cyclopropyl-3-(p-methylphenyl)prop-2-en-1-one；1-cyclopropyl-3-(4-methylphenyl)prop-2-en-1-one
• CAS: 56105-34-1
• 化学式: C₁₃H₁₄O
• 分子量: 186.254
• InChiKey: MQUOARGIVDGAGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  2-(p-Tolyl)-vinyl-cyclopropylketon 在 lithium aluminium tetrahydride 作用下， 生成 2-(p-Tolyl)ethyl cyclopropyl carbinol
  参考文献：
  名称：

  Antiviral activity of some .beta.-diketones. 1. Aryl alkyl diketones. In vitro activity against both RNA and DNA viruses

  摘要：

  The discovery that 4-[3-ethyl-6-[(3,4-methylenedioxy)phenyl]-3-hexenyl]-3,5-heptanedione (40) exhibited an in vitro inhibitory effect against equine rhinovirus led to a structure--activity study to establish the criteria for optimum activity. Modification of the bridge included removal of the ethyl group and reduction of the double bond. The heptanedione was replaced with hexanedione and pentanedione with a minimal effect. The effect of replacing the heptanedione with beta-keto esters and monoketones was also investigated. Maintaining the hexamethylene bridge and heptanedione, the methylenedioxy group was replaced with various substitutents. In general, most substituents did not adversely affect activity particularly against equine rhinovirus although there was some variation in activity against herpesvirus. Strongly hydrophilic groups significantly reduced activity. Finally, the effect of varying the length of the alkyl bridge was examined in the 4-hydroxyphenyl series, where peak activity was attained with n = 8.

  DOI：

  10.1021/jm00216a003
• 作为产物：
  描述：

  环丙甲基酮 、 对甲基苯甲醛 在 sodium hydroxide 作用下， 生成 2-(p-Tolyl)-vinyl-cyclopropylketon
  参考文献：
  名称：

  Antiviral activity of some .beta.-diketones. 1. Aryl alkyl diketones. In vitro activity against both RNA and DNA viruses

  摘要：

  The discovery that 4-[3-ethyl-6-[(3,4-methylenedioxy)phenyl]-3-hexenyl]-3,5-heptanedione (40) exhibited an in vitro inhibitory effect against equine rhinovirus led to a structure--activity study to establish the criteria for optimum activity. Modification of the bridge included removal of the ethyl group and reduction of the double bond. The heptanedione was replaced with hexanedione and pentanedione with a minimal effect. The effect of replacing the heptanedione with beta-keto esters and monoketones was also investigated. Maintaining the hexamethylene bridge and heptanedione, the methylenedioxy group was replaced with various substitutents. In general, most substituents did not adversely affect activity particularly against equine rhinovirus although there was some variation in activity against herpesvirus. Strongly hydrophilic groups significantly reduced activity. Finally, the effect of varying the length of the alkyl bridge was examined in the 4-hydroxyphenyl series, where peak activity was attained with n = 8.

  DOI：

  10.1021/jm00216a003

文献信息

• Pyrrolidine derivatives
  申请人：Societe Anonyme dite: Hexachimie

  公开号：US04005103A1

  公开（公告）日：1977-01-25

  The invention provides compounds of formula ##STR1## wherein R and R' are hydrogen, halogen, alkyl, alkoxy, trihalomethyl or hydroxy or they together form methylenedioxy, R" is hydrogen or methyl, and R"' is hydrogen, alkyl, benzyl, propargyl or hydroxyethyl, or salts thereof. The compounds are useful as anorexigenic or analeptic agents.

  该发明提供了公式##STR1##的化合物，其中R和R'是氢，卤素，烷基，烷氧基，三卤甲基或羟基，或者它们一起形成亚甲二氧基，R"是氢或甲基，R"'是氢，烷基，苄基，丙炔基或羟乙基，或其盐。这些化合物可用作压抑食欲或兴奋剂。
• Carbocation-Catalyzed Intramolecular and Intermolecular Carbonyl-Alkyne Metathesis Reactions
  作者：Jasnoor S. Mann、Binh Khanh Mai、Thanh Vinh Nguyen

  DOI：10.1021/acscatal.2c06016

  日期：2023.2.17

  metathesis (CAM) reaction is a versatile, stereoselective, and atom-economical method to access a diverse range of α,β-unsaturated carbonyl compounds, which are useful synthetic precursors and constitute an important structural motif in biologically active substances. In this work, we developed an efficient organic Lewis acid catalytic system to promote both the intramolecular and intermolecular CAM reactions

  羰基-炔烃复分解 (CAM) 反应是一种多功能、立体选择性和原子经济的方法，可用于获取各种 α,β-不饱和羰基化合物，这些化合物是有用的合成前体，构成生物活性物质中的重要结构基序。在这项工作中，我们开发了一种有效的有机路易斯酸催化体系，以促进分子内和分子间 CAM 反应。对于其他已建立的 CAM 催化剂，很少证明这种多功能催化活性。我们的无金属方案应用于广泛的底物，以产生多种有用的有机结构。
• Copper-Catalyzed Aza-Benzyl Transfer Michael Addition via C–C Bond Cleavage
  作者：Si-Qi Xiong、Chuan-Ming Hong、Qing-Hua Li、Tang-Lin Liu

  DOI：10.1021/acs.joc.2c02740

  日期：2023.3.17

  A non-noble Cu-catalyzed transfer aza-benzyl Michael addition via the C–C bond cleavage of aza-benzyl alcohols has been disclosed. The unstrained C(sp3)–C(sp3) bond of an alcohol was selectively cleaved. This aza-benzyl transfer strategy provides a selective and environmentally benign approach for the C-alkylation of α,β-unsaturated carbonyl compounds that employs readily available alcohols as carbon

  已经公开了通过氮杂苯甲醇的 C-C 键裂解的非贵金属 Cu 催化转移氮杂苯甲基迈克尔加成。醇的未应变 C(sp 3 )–C(sp 3 ) 键被选择性裂解。这种氮杂-苄基转移策略为 α,β-不饱和羰基化合物的 C-烷基化提供了一种选择性和环境友好的方法，该方法使用现成的醇作为碳亲核试剂，其特点是底物范围广，产率高。
• Kinetic Resolution of N-Allylic Pyrazoles via Photoexcited Chiral Copper Complex-Catalyzed Alkene E → Z Isomerization
  作者：Liang Liu、Shiqi Ren、Shouyun Yu

  DOI：10.1021/acs.orglett.4c01220

  日期：2024.6.28

  Herein, we present an efficient and practical kinetic resolution (KR) of racemic allylic pyrazoles utilizing photoexcited chiral-copper-complex-mediated alkene E → Z isomerization. This method enables the synthesis of both enantioenriched E- and Z-allylic pyrazoles, achieving enantiomeric excesses (e.e.) of up to 97% and selectivity factors (S factors) as high as 217. Remarkably, the method’s ability

  在此，我们提出了一种利用光激发手性铜配合物介导的烯烃E → Z异构化外消旋烯丙基吡唑的高效实用的动力学拆分 (KR)。该方法能够合成对映体富集的E-和Z-烯丙基吡唑，对映体过量 (ee) 高达 97%，选择性因子 ( S因子) 高达 217。值得注意的是，该方法能够为烯丙基吡唑提供Z构型在热力学控制下特别难以获得，强调了该合成方案的变革潜力。