ethyl 2-butoxy-3,4-dihydro-6-phenyl-2H-pyran-5-carboxylate | 1256543-90-4

• 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: ethyl 2-butoxy-3,4-dihydro-6-phenyl-2H-pyran-5-carboxylate
• 英文别名: ethyl 2-butoxy-6-phenyl-3,4-dihydro-2H-pyran-5-carboxylate
• CAS: 1256543-90-4
• 化学式: C₁₈H₂₄O₄
• 分子量: 304.386
• InChiKey: AVKQMMYVTPHFRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.91
• 重原子数：
  22.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-butoxy-3,4-dihydro-6-phenyl-2H-pyran-5-carboxylate 在 manganese(II) chloride tetrahydrate 作用下， 以 硝基甲烷 为溶剂， 反应 11.0h， 以56%的产率得到ethyl β-oxo-α-(3-oxopropyl)benzenepropanoate
  参考文献：
  名称：

  氯化锰作为酮羰基存在下吲哚选择性转化的有效催化剂

  摘要：

  已发现四水合氯化锰催化对吲哚的选择性转化有效，可以促进所需的酸催化反应，同时，还需要酸的辅助副反应，吲哚的亲电反应与并存的酮羰基不发生。可以顺利进行某些酸催化的反应，例如2-烷氧基-3,4-二氢吡喃与吲哚的开环反应，以及β-酮酸酯与含有C-3未取代的吲哚片段的醇的酯交换反应通过使用氯化锰作为催化剂。氯化锰催化还开发了吲哚，3,4-二氢吡喃和β-酮酸酯的新的多组分反应。

  DOI：

  10.1002/adsc.201100211
• 作为产物：
  描述：

  乙烯基正丁醚 、 2-(羟基苯基甲基)丙烯酸乙酯 在 2-碘酰基苯甲酸 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以51%的产率得到ethyl 2-butoxy-3,4-dihydro-6-phenyl-2H-pyran-5-carboxylate
  参考文献：
  名称：

  Baylis-Hillman 加合物与富电子烯烃在 IBX 存在下的氧化 oxoDiels-Alder 反应

  摘要：

  摘要 Baylis-Hillman 加合物被碘氧基苯甲酸 (IBX) 氧化为 2-methylene-1,3-dicarbonyl 化合物，该化合物可以作为氧二烯与富电子烯烃反应生成各种氧代 Diels-Alder 加合物，收率良好. 图形概要

  DOI：

  10.1080/00397911.2010.541967

文献信息

• Ring-Opening Reactions of 2-Alkoxy-3,4-dihydropyrans with Thiols or Thiophenols
  作者：Minghao Li、Haoquan Li、Tao Li、Yanlong Gu

  DOI：10.1021/ol103110q

  日期：2011.3.4

  An electrophilic ring-opening reaction of 2-alkoxy-3,4-dihydropyran with a thiophenol or thiol is developed for the first time. The generated product contains not only a 1,3-dicarbonyl moiety but also a fragment of bis(alkylthio)methane. A possible mechanism is also proposed on the basis of postulating a ring-opening monotransthioacetalization product, which was prepared by using LiBr as catalyst as

  首次开发了2-烷氧基-3,4-二氢吡喃与硫酚或硫醇的亲电开环反应。产生的产物不仅包含1，3-二羰基部分，而且还包含双（烷硫基）甲烷的片段。在假定开环单反硫代缩醛化产物的基础上，还提出了一种可能的机理，该产物是使用LiBr作为催化剂制备的。
• From Waste Biomass to Solid Support: Lignosulfonate as a Cost-Effective and Renewable Supporting Material for Catalysis
  作者：Shaohuan Sun、Rongxian Bai、Yanlong Gu

  DOI：10.1002/chem.201303364

  日期：2014.1.7

  2) lignin‐SO3Cu(OTf), and 3) lignin‐IL@NH2 (IL=ionic liquid). These solid materials were then examined in many organic transformations. It was finally found that, compared with its homogeneous counterpart as well as some other solid catalysts that are prepared by using different supports with the same metal or catalytically active species, the lignin‐supported catalysts showed better performance in these reactions

  木质素磺酸盐（LS）是有机废物，是造纸过程中亚硫酸盐制浆过程中蒸煮过程的副产品。本文将LS用作固定阳离子物种的阴离子载体材料，然后将其用作某些有机转化中的非均相催化剂。与此策略，制备了三种木质素为载体的催化剂进行，包括1）木质素-SO 3钪（OTF）2，2）木质素-SO 3的Cu（OTF），和3）木质素IL @ NH 2（IL ＝离子液体）。然后在许多有机转化中检查了这些固体材料。最终发现，与同质对应物以及通过使用具有相同金属或催化活性物种的不同载体制备的其他一些固体催化剂相比，木质素负载的催化剂不仅在以下方面表现出更好的性能：活动，也涉及可回收性。
• 2-Alkoxy-3,4-dihydropyrans as modular substrates to construct polyheterocycles by reacting with NH2-containing bisnucleophiles
  作者：Jing Yang、Shaohuan Sun、Biao Zhang、Juan Zhang、Yanlong Gu

  DOI：10.1016/j.tet.2014.10.023

  日期：2014.12

  2-Alkoxy-3,4-dihydropyrans were proved to be a class of powerful modular substrates to construct polyheterocycles by reacting with NH2-containing dinucleophiles, such as anthranilamide, 2-aminobenzenethiol, 1-(2-aminophenyl)pyrrole, and 2-(o-aminophenyl)indole in the presence of LiBr·H2O. A three-component reaction of isatoic anhydride, 2-alkoxy-3,4-dihydropyran and amine was also developed as well

  通过与含NH 2的二亲核试剂（如邻氨基苯甲酰胺，2-氨基苯硫醇，1-（2-氨基苯基）吡咯和2）反应，证明2-烷氧基-3,4-二氢吡喃是一类强大的模块化底物，可用于构建多杂环。-（邻氨基苯基）吲哚在LiBr·H 2 O的存在下。还开发了等角酸酐，2-烷氧基-3,4-二氢吡喃和胺的三组分反应。
• Gluconic acid aqueous solution: a task-specific bio-based solvent for ring-opening reactions of dihydropyrans
  作者：Jie Yang、Binghua Zhou、Minghao Li、Yanlong Gu

  DOI：10.1016/j.tet.2012.11.076

  日期：2013.1

  Gluconic acid aqueous solution (GAAS) that is a largely available bio-based chemical was proved to be an effective task-specific medium for ring-opening reactions of dihydropyrans. In the presence of nucleophiles, such as indoles, 1,3-cyclohexanediones, N,N-dimethylaniline, N-methylaniline, 2-naphthol, and resorcin, a series of 2-substituted 1, 3-dicarbonyl compounds were synthesized in good to excellent yields. The first example of ring-opening of oxa-Pictet-Spengler product with nucleophiles was also described. These results not only demonstrate the feasibility of using GAAS as a sustainable solvent, but also offer an effective way for the ring-opening reactions of dihydropyrans with nucleophiles. Because these reactions proceeded with excellent atom-economy in a sustainable bio-based solvent, the present method was thus characterized by many properties of green chemistry, such as green solvent, atom-economy, and utilization of bio-based chemicals. (C) 2012 Elsevier Ltd. All rights reserved.