4-(p-tolyl)-5,6-dihydro-2H-pyran-2-one | 24060-19-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 4-(p-tolyl)-5,6-dihydro-2H-pyran-2-one
• 英文别名: 4-(4-Methylphenyl)-2,3-dihydropyran-6-one；4-(4-methylphenyl)-2,3-dihydropyran-6-one
• CAS: 24060-19-3
• 化学式: C₁₂H₁₂O₂
• 分子量: 188.226
• InChiKey: LZQMRCAFBIVXND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(p-tolyl)-5,6-dihydro-2H-pyran-2-one 在 吡啶 、 盐酸羟胺 、 potassium tert-butylate 、 二异丁基氢化铝 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 、 环己烷 为溶剂， 反应 25.5h， 生成 (1E,3E)-1-phenyl-3-(p-tolyl)hexa-3,5-dien-1-one oxime
  参考文献：
  名称：

  Catalytic Enantioselective 1,4-Iodofunctionalizations of Conjugated Dienes

  摘要：

  The first catalytic enantioselective 1,4-iodofunctionalizations of conjugated dienes have been developed. Starting from beta,gamma,delta,epsilon-unsaturated oximes and 4-Ns hydrazones, these N-iodosuccinimide-mediated reactions are catalyzed by newly modified tertiary aminothiourea derivatives and furnish Delta(2)-isoxazoline and Delta(2)-pyrazoline derivatives, respectively, containing an (E)-allyl iodide group at the quaternary stereogenic center generally in high yield and with excellent enantioselectivity (up to 98.5:1.5 er).

  DOI：

  10.1021/acs.orglett.5b02026
• 作为产物：
  描述：

  4-甲苯硼酸 、 methyl 5-[1-(tert-butyl)-1,1-dimethylsilyl]oxy-2-pentynoate 在 copper (I) acetate 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 7.0h， 以88%的产率得到4-(p-tolyl)-5,6-dihydro-2H-pyran-2-one
  参考文献：
  名称：

  Synthesis of 4-Aryl-Substituted Butenolides and Pentenolides by Copper-Catalyzed Hydroarylation

  摘要：

  We have investigated the effect of the type of protecting group used and the tether length of 4- and 5-hydroxy-substituted 2-alkynoates on the yields and selectivity of the product of hydroarylation. The use of methyl, methoxymethyl, and tert-butyldimethylsilyl (TBS) as protecting groups increased the total yield of the products. While the protected 4-hydroxy-2-butynoates afforded products formed from two or more alkyne substrates, 5-hydroxy-2-pentynoate derivatives exclusively yielded 1:1 adducts. These facts suggest that the product selectivity depends on the distance of the alkoxy group from the alkyne moiety rather than the type of the protecting group. Among the protecting groups used in this study, the TBS group was found to produce butenolides and pentenolides in good total yields via the one-pot hydroarylation/lactonization.

  DOI：

  10.3987/com-09-s(s)8

文献信息

• Palladium-Catalyzed Regioselective [5 + 1] Annulation of Vinyl Aziridines/Epoxides with ClCF₂COONa
  作者：Dandan Zuo、Tao Zhang、Jingjing Zhao、Wen Luo、Chaojie Wang、Pan Li

  DOI：10.1021/acs.orglett.2c01739

  日期：2022.7.1

  regioselective [5 + 1] annulation reactions of vinyl aziridines/epoxides with ClCF2COONa have been developed. Significantly, vinyl aziridines/epoxides act as heteroatom-containing five-atom synthons, and commercially available and cheap ClCF2COONa acts as the source of carbonyl serving as a difluorocarbene precursor. This protocol provides an efficient and practical method for the synthesis of δ-lactams and

  已经开发了钯催化的乙烯基氮丙啶/环氧化物与 ClCF 2 COONa 的区域选择性 [5 + 1] 环化反应。重要的是，乙烯基氮丙啶/环氧化物充当含杂原子的五原子合成子，而市售且廉价的 ClCF 2 COONa 充当用作二氟卡宾前体的羰基来源。该协议为以良好收率合成 δ-内酰胺和 δ-内酯提供了一种有效且实用的方法。
• 一种钯催化条件下合成α,β-不饱和杂环己基酮类化合物的方法
  申请人：河南大学

  公开号：CN114853664B

  公开（公告）日：2023-09-29

  本发明属于化合物制备技术领域，具体涉及一种钯催化条件下合成α,β‑不饱和杂环己基酮类化合物的方法，该方法是以式I所示的化合物和式II所示的ClCF2CO2Na为原料，在催化剂、配体、碱和溶剂作用下，所述催化剂为钯催化剂，在惰性气氛条件下发生环化反应，即烯基氮杂环丙烷/烯基环氧乙烷氧化开环，与ClCF2CO2Na提供的二氟卡宾形成配合物，该配合物在迁移插入和还原消除后，最终形成目标产物α,β‑不饱和杂环己基酮类化合物。本发明工艺简单，收率高。本发明中催化剂醋酸钯和配体三环己基膦，价格低，不需要过多处理；反应步骤简单，能以可观的产率获得相应产物。
• Palladium-Catalyzed Carbonylative [5+1] Cycloaddition of <i>N</i>-Tosyl Vinylaziridines: Solvent-Controlled Divergent Synthesis of α,β- and β,γ-Unsaturated δ-Lactams
  作者：Tao Zhang、Shichong Wang、Dandan Zuo、Jingjing Zhao、Wen Luo、Chaojie Wang、Pan Li

  DOI：10.1021/acs.joc.2c00710

  日期：2022.8.5
• Catalytic Enantioselective 1,4-Iodofunctionalizations of Conjugated Dienes
  作者：Chandra Bhushan Tripathi、Santanu Mukherjee

  DOI：10.1021/acs.orglett.5b02026

  日期：2015.9.18

  The first catalytic enantioselective 1,4-iodofunctionalizations of conjugated dienes have been developed. Starting from beta,gamma,delta,epsilon-unsaturated oximes and 4-Ns hydrazones, these N-iodosuccinimide-mediated reactions are catalyzed by newly modified tertiary aminothiourea derivatives and furnish Delta(2)-isoxazoline and Delta(2)-pyrazoline derivatives, respectively, containing an (E)-allyl iodide group at the quaternary stereogenic center generally in high yield and with excellent enantioselectivity (up to 98.5:1.5 er).
• Synthesis of 4-Aryl-Substituted Butenolides and Pentenolides by Copper-Catalyzed Hydroarylation
  作者：Yoshihiko Yamamoto、Naohiro Kirai

  DOI：10.3987/com-09-s(s)8

  日期：——

  We have investigated the effect of the type of protecting group used and the tether length of 4- and 5-hydroxy-substituted 2-alkynoates on the yields and selectivity of the product of hydroarylation. The use of methyl, methoxymethyl, and tert-butyldimethylsilyl (TBS) as protecting groups increased the total yield of the products. While the protected 4-hydroxy-2-butynoates afforded products formed from two or more alkyne substrates, 5-hydroxy-2-pentynoate derivatives exclusively yielded 1:1 adducts. These facts suggest that the product selectivity depends on the distance of the alkoxy group from the alkyne moiety rather than the type of the protecting group. Among the protecting groups used in this study, the TBS group was found to produce butenolides and pentenolides in good total yields via the one-pot hydroarylation/lactonization.