(R)-2-ethoxycarbonyl-2,3-dihydro-2-methylpyran-4-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: (R)-2-ethoxycarbonyl-2,3-dihydro-2-methylpyran-4-one
• 英文别名: (R)-2-methyl-4-oxo-3,4-dihydro-2H-pyran-2-carboxylic acid ethyl ester；ethyl 2-methyl-4-oxo-3,4-dihydro-2H-pyran-2-carboxylate；ethyl (2R)-2-methyl-4-oxo-3H-pyran-2-carboxylate
• 化学式: C₉H₁₂O₄
• 分子量: 184.192
• InChiKey: NHLRCCGSQOIUOW-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  丙酮酸乙酯 、 反-1-甲氧基-3-(三甲基硅氧基)-1,3-丁二烯 在 chiral bis(oxazoline)-copper 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以52%的产率得到(R)-2-ethoxycarbonyl-2,3-dihydro-2-methylpyran-4-one
  参考文献：
  名称：

  通往季碳中心的不对称杂Diels-Alder路线：(−)-malyngolide的合成

  摘要：

  构象约束的手性双(恶唑啉)-金属配合物催化达尼塞夫斯基二烯和多种α-酮酯的不对称杂狄尔斯-阿尔德反应，对映选择性地构建了季碳中心。该反应用于合成(-)-马林高内酯。

  DOI：

  10.1016/s0040-4039(01)01227-8

文献信息

• Asymmetric hetero‐Diels‐Alder Reaction of <i>trans</i> ‐1‐Methoxy‐3‐trimethylsilyloxy‐buta‐1,3‐diene Catalyzed by Zinc Complexes
  作者：Matylda Stefaniak、Szymon Buda、Jacek Mlynarski

  DOI：10.1002/ejoc.202000822

  日期：2020.9.7

  Catalytic asymmetric hetero‐Diels‐Alder (hDA) reaction of Danishefsky diene with α‐carbonyl esters have been performed with a zinc‐based catalyst that is readily available from zinc triflate and bisoxazoline ligands.

  DAnishefsky二烯与α-羰基酯的不对称杂Diels-Alder（hDA）催化反应已通过锌基催化剂进行，该锌基三氟甲磺酸锌和双恶唑啉配体很容易获得。
• A versatile catalyst for asymmetric reactions of carbonyl groups working purely by activation through hydrogen bonding: Mukaiyama-aldol, hetero Diels–Alder and Friedel–Crafts reactions
  作者：Wei Zhuang、Thomas B. Poulsen、Karl Anker Jørgensen

  DOI：10.1039/b507778h

  日期：——

  to be promising candidates for the efficient activation of carbonyl compounds through hydrogen bonding. Exemplified by three carbonyl addition reactions: Mukaiyama-aldol, hetero Diels-Alder and Friedel-Crafts reactions we show that bis-triflamides or bis-nonaflamides of commercially available chiral diamines act as chiral Bronsted-acid catalysts, leading to the optically active products in moderate

  已证明双磺酰胺是通过氢键有效活化羰基化合物的有前途的候选物。以三个羰基加成反应为例：Mukaiyama-aldol，杂Diels-Alder和Friedel-Crafts反应，我们发现市售手性二胺的双-三氟化物或双-九氟化物充当手性布朗斯台德酸催化剂，从而导致中等至优异的收率，对映选择性高达73％ee。
• Chiral dihydropyranones via hetero Diels–Alder reaction of Danishefsky's diene and α-ketoesters: a high-throughput screening approach
  作者：Christian Wolf、Zaid Fadul、Pili A. Hawes、Emily C. Volpe

  DOI：10.1016/j.tetasy.2004.05.024

  日期：2004.7

  The chiral Lewis acid-catalyzed hetero Diels-Alder reaction between Danishefsky's diene and sterically hindered alpha-ketoesters has been optimized using a validated high-throughput screening method. The yields and enantioselectivities of three chiral dihydropyranones obtained by this multi-substrate one-pot screening approach are in excellent agreement with individual screening results. Employing ethyl benzoylformate, ethyl 3-methyl-2-oxobutyrate, and dihydro-4,4-dimethyl-2,3-furandione in one reaction mixture allowed a fast evaluation of chiral Lewis acid composition, solvent, temperature, catalyst loading, and dienophile concentration. The crude product mixtures were analyzed by HPLC using two chiral stationary phases coupled in series to avoid time-consuming work-up procedures. (C) 2004 Elsevier Ltd. All rights reserved.