1,3-dioxane-2-carboxylic acid | 204527-26-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二恶烷
• 英文名称: 1,3-dioxane-2-carboxylic acid
• CAS: 204527-26-4
• 化学式: C₅H₈O₄
• mdl: MFCD19231855
• 分子量: 132.116
• InChiKey: AFWWNXOSDUHYFQ-UHFFFAOYSA-N

物化性质

• 沸点：
  278.3±35.0 °C(Predicted)
• 密度：
  1.310±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,3-dioxane-2-carboxylic acid 、 甘氨酸苄酯对甲苯磺酸盐 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以3.16 g的产率得到benzyl [([1,3]-dioxane-2-carbonyl)amino]acetate
  参考文献：
  名称：

  Direct anti-selective asymmetric hydrogenation of α-amino-β-keto esters through dynamic kinetic resolution using Ru-axially chiral phosphine catalysts—stereoselective synthesis of anti-β-hydroxy-α-amino acids

  摘要：

  The asymmetric hydrogenation of alpha-amino-beta-keto esters using ruthenium (Ru) anti-selectively proceeds via a dynamic kinetic resolution to afford anti-beta-hydroxy-alpha-amino acids with high enantiomeric purities, which are important chiral building blocks for the synthesis of medicines and natural products. A mechanistic investigation has revealed that the Ru-catalyzed asymmetric hydrogenation takes place via the hydrogenation of the double bond in the enol tautomer of the substrate. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.12.024
• 作为产物：
  描述：

  乙基1,3-二恶烷-2-羧酸酯 在 sodium hydroxide 、 水 作用下， 以 乙醇 为溶剂， 生成 1,3-dioxane-2-carboxylic acid
  参考文献：
  名称：

  Direct anti-selective asymmetric hydrogenation of α-amino-β-keto esters through dynamic kinetic resolution using Ru-axially chiral phosphine catalysts—stereoselective synthesis of anti-β-hydroxy-α-amino acids

  摘要：

  The asymmetric hydrogenation of alpha-amino-beta-keto esters using ruthenium (Ru) anti-selectively proceeds via a dynamic kinetic resolution to afford anti-beta-hydroxy-alpha-amino acids with high enantiomeric purities, which are important chiral building blocks for the synthesis of medicines and natural products. A mechanistic investigation has revealed that the Ru-catalyzed asymmetric hydrogenation takes place via the hydrogenation of the double bond in the enol tautomer of the substrate. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.12.024

文献信息

• Visible‐Light‐Promoted Nickel‐ and Organic‐Dye‐Cocatalyzed Formylation Reaction of Aryl Halides and Triflates and Vinyl Bromides with Diethoxyacetic Acid as a Formyl Equivalent
  作者：He Huang、Xiangmin Li、Chenguang Yu、Yueteng Zhang、Patrick S. Mariano、Wei Wang

  DOI：10.1002/anie.201610108

  日期：2017.2

  synergistic nickel‐ and organic‐dye‐mediated photoredox catalysis is reported. Distinct from widely used palladium‐catalyzed formylation processes, this reaction proceeds by a two‐step mechanistic sequence involving initial in situ generation of the diethoxymethyl radical from diethoxyacetic acid by a 4CzIPN‐mediated photoredox reaction. The formyl‐radical equivalent then undergoes nickel‐catalyzed substitution

  据报道，在协同的镍和有机染料介导的光氧化还原催化下，芳基卤化物，芳基三氟甲磺酸酯和乙烯基溴化物发生了简单的甲酰化反应。与广泛使用的钯催化的甲酰化工艺不同，该反应通过两步机理进行，该过程涉及通过4CzIPN介导的光氧化还原反应从二乙氧基乙酸中原位生成二乙氧基甲基自由基。然后，甲酰基自由基与芳基卤化物，三氟甲磺酸酯和乙烯基溴化物进行镍催化的取代反应，形成相应的醛产物。重要的是，除了芳基溴化物之外，反应性较低的芳基氯和三氟甲磺酸酯和乙烯基卤化物可作为该方法的有效底物。由于该反应所涉及的温和条件可以耐受过多的官能团，