Benzyl 2-[acetyloxy(phenyl)methyl]prop-2-enoate | 666749-21-9

• 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: Benzyl 2-[acetyloxy(phenyl)methyl]prop-2-enoate
• CAS: 666749-21-9
• 化学式: C₁₉H₁₈O₄
• 分子量: 310.35
• InChiKey: YZWADWLCYZLFBI-UHFFFAOYSA-N

物化性质

• 沸点：
  436.6±45.0 °C(Predicted)
• 密度：
  1.157±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  联硼酸频那醇酯 、 Benzyl 2-[acetyloxy(phenyl)methyl]prop-2-enoate 在 potassium acetate 、 copper(l) chloride 、 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以97%的产率得到benzyl (E)-3-phenyl-2-[(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)methyl]prop-2-enoate
  参考文献：
  名称：

  Novel Functionalized Trisubstituted Allylboronates via Hosomi−Miyaura Borylation of Functionalized Allyl Acetates

  摘要：

  A series of novel functionalized achiral and chiral allylboronates have been synthesized via the nucleophilic addition of boronates on allyl acetates derived via vinylalumination or Baylis-Hillman reaction of aldehydes. These reagents, upon allylboration with aldehydes, furnish,beta-substituted-alpha-methylene-gamma-butyrolactones stereoselectively.

  DOI：

  10.1021/ol035952z
• 作为产物：
  描述：

  丙炔酸苄酯 在 吡啶 、 N-甲基吲哚酮 、 二异丁基氢化铝 作用下， 生成 Benzyl 2-[acetyloxy(phenyl)methyl]prop-2-enoate
  参考文献：
  名称：

  Novel Functionalized Trisubstituted Allylboronates via Hosomi−Miyaura Borylation of Functionalized Allyl Acetates

  摘要：

  A series of novel functionalized achiral and chiral allylboronates have been synthesized via the nucleophilic addition of boronates on allyl acetates derived via vinylalumination or Baylis-Hillman reaction of aldehydes. These reagents, upon allylboration with aldehydes, furnish,beta-substituted-alpha-methylene-gamma-butyrolactones stereoselectively.

  DOI：

  10.1021/ol035952z

文献信息

• PYRIDOPYRIMIDINE BASED DERIVATIVES AS POTENTIAL PHOSPHODIESTERASE 3 (PDE3) INHIBITORS AND A PROCESS FOR THE PREPARATION THEREOF
  申请人：COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH

  公开号：US20140221651A1

  公开（公告）日：2014-08-07

  The present invention provides compounds of formula 1 as potential phosphodiesterase3 (PDE3) inhibitory agents and a process for the preparation thereof. The derivatives of formula 1 can be employed as therapeutics in human and veterinary medicine, where they can be used, for the treatment and prophylaxis of the following diseases: heart failure, dilated cardiomyopathy, platelet inhibitors, cancer and obstructive pulmonary diseases. Where in X=H, alkyl, aryl, heteroaryl Y=H, alkyl, aryl, heteroaryl R=substituted phenyl A=H, alkyl, alkoxy, halo, dihalo B=H, alkyl, alkoxy, halo, dihalo C=H, alkyl, alkoxy, halo, dihalo

  本发明提供了公式1的化合物作为潜在的磷酸二酯酶3（PDE3）抑制剂，并提供了其制备方法。公式1的衍生物可以作为人类和兽医药学中的治疗药物使用，用于治疗和预防以下疾病：心力衰竭、扩张型心肌病、血小板抑制剂、癌症和阻塞性肺部疾病。其中，X=H、烷基、芳基、杂环芳基；Y=H、烷基、芳基、杂环芳基；R=取代苯基；A=H、烷基、烷氧基、卤素、二卤代基；B=H、烷基、烷氧基、卤素、二卤代基；C=H、烷基、烷氧基、卤素、二卤代基。
• Enantioselective Radical S_N2-Type Alkylation of Morita–Baylis–Hillman Adducts Using Dual Photoredox/Palladium Catalysis
  作者：Xiangbin Bai、Linlin Qian、Hong-Hao Zhang、Shouyun Yu

  DOI：10.1021/acs.orglett.1c03064

  日期：2021.11.5

  An enantioselective radical alkylation of 4-alkyl-1,4-dihydropyridines with Morita–Baylis–Hillman (MBH) adducts has been reported. The SN2-type products are predominant. This reaction is enabled by dual photoredox/palladium catalysis. The alkylation products are provided in good yields with good regio- and enantioselectivity. The use of Ding’s spiroketal-based bis(phosphine) (SKP) ligand is crucial

  已经报道了 4-烷基-1,4-二氢吡啶与 Morita-Baylis-Hillman (MBH) 加合物的对映选择性自由基烷基化。S N 2 型产品占主导地位。该反应是通过双光氧化还原/钯催化实现的。烷基化产物以良好的产率和良好的区域选择性和对映选择性提供。Ding 的基于螺缩酮的双（膦）（SKP）配体的使用对于实现令人满意的区域选择性和对映选择性至关重要。生成的 α,β-不饱和酯可以很容易地还原为合成有用的手性烯丙醇。
• Organophotoredox-Catalyzed Arylation and Aryl Sulfonylation of Morita–Baylis–Hillman Acetates with Diaryliodonium Reagents
  作者：Sudip Senapati、Sushanta Kumar Parida、Sayali Sunil Karandikar、Sandip Murarka

  DOI：10.1021/acs.orglett.3c03146

  日期：2023.11.3

  organophotoredox-catalyzed stereoselective allylic arylation of MBH acetates with a palette of diaryliodonium triflates (DAIRs) to provide the corresponding trisubstituted alkenes in moderate to good yields. The method could be extended to three-component coupling involving 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct (DABSO) as a sulfur dioxide surrogate for the synthesis of biologically relevant

  我们报道了一种有机光氧化还原催化的 MBH 乙酸酯与二芳基碘鎓三氟甲磺酸盐 (DAIR) 的立体选择性烯丙基芳基化反应，以中等至良好的产率提供相应的三取代烯烃。该方法可以扩展到三组分偶联，涉及 1,4-二氮杂双环[2.2.2]辛烷双（二氧化硫）加合物（DABSO）作为二氧化硫替代物，用于合成生物学相关的烯丙基砜。这两个反应都是在温和的条件下进行的，具有广泛的范围、稳健性和明显的官能团耐受性。
• Photoinduced Alkylsulfonylation and Cyanoalkylsulfonylation of Morita–Baylis–Hillman Adducts via Multicomponent Insertion of Sulfur Dioxide
  作者：Zhi-Jie Song、Yu Bao、Yun-Jia Sun、Shenghu Yan、Yue Zhang、Guigen Li、Jia-Yin Wang

  DOI：10.1021/acs.joc.4c00052

  日期：2024.4.5

  alkylsulfonylation and cyanoalkylsulfonylation of MBH adducts have been developed through the multicomponent insertion of sulfur dioxide, enabling the assembly of two C–S bonds to generate structurally diverse allylic alkylsulfones (43 examples in total). The reaction of MBH adducts with potassium alkyltrifluoroborates and 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct afforded sulfones with generally good

  通过二氧化硫的多组分插入，开发了通用且方便的可见光促进的MBH加合物烷基磺酰化和氰基烷基磺酰化，使得两个C-S键组装能够生成结构多样的烯丙基烷基砜（总共43个例子）。 MBH加合物与烷基三氟硼酸钾和1,4-二氮杂双环[2.2.2]辛烷双(二氧化硫)加合物反应得到了具有良好产率的砜。值得注意的是，将N ， N ， N '， N'-四甲基乙二胺作为碱添加到光催化体系中，利用环酮肟酯作为C自由基前体，产生烷基磺酰基单元和氰基锚定的三取代烯烃。这两个反应都构建了两个 C-S 键，并且以中等至优异的产率获得了所有所需的产物，并且具有完全的立体特异性。
• US9242982B2
  申请人：——

  公开号：US9242982B2

  公开（公告）日：2016-01-26