ethyl 2-acetoxy-3-oxohexanoate | 37447-23-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: ethyl 2-acetoxy-3-oxohexanoate
• 英文别名: Ethyl 2-acetyloxy-3-oxohexanoate
• CAS: 37447-23-7
• 化学式: C₁₀H₁₆O₅
• 分子量: 216.234
• InChiKey: ZVPLZWQQLGEIAY-UHFFFAOYSA-N

物化性质

• 沸点：
  296.4±25.0 °C(predicted)
• 密度：
  1.091±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-acetoxy-3-oxohexanoate 在 磺酰氯 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 ethyl 6-methyl-2-propylpyridine-3-carboxylate
  参考文献：
  名称：

  The preparation of 1,2,4-triazines from α,β-diketo-ester equivalents and their application in pyridine synthesis

  摘要：

  The alpha-Chloro-alpha-acetoxy-beta-keto-esters were prepared from beta-keto-esters in good overall yields. These compounds reacted as alpha,beta-diketo-ester equivalents with amidrazones yielding triazines, generally in good yields, or with an amidrazone and 2,5-norbornadiene in a one-pot aza Diels-Alder reaction to give the corresponding pyridines. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.06.163
• 作为产物：
  描述：

  丁酰乙酸乙酯 在 磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 ethyl 2-acetoxy-3-oxohexanoate
  参考文献：
  名称：

  The preparation of 1,2,4-triazines from α,β-diketo-ester equivalents and their application in pyridine synthesis

  摘要：

  The alpha-Chloro-alpha-acetoxy-beta-keto-esters were prepared from beta-keto-esters in good overall yields. These compounds reacted as alpha,beta-diketo-ester equivalents with amidrazones yielding triazines, generally in good yields, or with an amidrazone and 2,5-norbornadiene in a one-pot aza Diels-Alder reaction to give the corresponding pyridines. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.06.163

文献信息

• Novel and Effective Synthesis of 2-Acyloxy-3-keto Esters
  作者：Sadao Tsuboi、Takuzo Komiyama、Yutaka Takaguchi

  DOI：10.1055/s-2006-926468

  日期：2006.6

  A one-pot effective synthesis of 2-acyloxy-3-keto ester is reported. Treatment of 2-chloroglycidic esters with carboxylate salts in acetonitrile provided 2-acyloxy-3-keto esters in excellent to reasonable yields.

  报道了一种一锅法有效合成 2-酰氧基-3-酮酯的方法。在乙腈中用羧酸盐处理 2-氯缩水甘油酯以优异至合理的产率提供了 2-酰氧基-3-酮酯。
• Stereoselective Mannich Reaction of <i>α</i> ‐Acetoxy‐ <i>β</i> ‐keto Esters with Isatin Imine: An Efficient Access to Vicinal Tetra‐Substituted Stereocenters
  作者：Jasneet Kaur、Banni Preet Kaur、Nasarul Islam、Pankaj Chauhan、Swapandeep Singh Chimni

  DOI：10.1002/ejoc.202101047

  日期：2021.10.7

  Synthesis of optically active 3-substituted-3-aminooxindoles containing vicinal quaternary stereogenic centers was achieved using a quinine thiourea organocatalyst. α-Acetoxy-β-keto esters have been introduced as nucleophiles to undergo Mannich reaction with isatin imines for asymmetric organocatalysis.

  使用奎宁硫脲有机催化剂合成了含有邻位四元立体中心的光学活性 3-取代-3-氨基羟吲哚。α-乙酰氧基-β-酮酯已被引入作为亲核试剂与靛红亚胺进行曼尼希反应以进行不对称有机催化。
• A convenient synthesis of pyridine and 2,2′-bipyridine derivatives
  作者：Marta Altuna-Urquijo、Alexander Gehre、Stephen P. Stanforth、Brian Tarbit

  DOI：10.1016/j.tet.2008.11.090

  日期：2009.1

  alpha-Chloro-alpha-acetoxy-beta-keto-esters 9 were readily prepared from beta-keto-esters 6 in good overall yields. These compounds reacted as alpha,beta-diketo-ester equivalents 2 with amidrazones 1 yielding triazines 3, generally in good yields. Picolinates 10 provided an alternative source of alpha,beta-diketo-ester equivalents 2 when treated with copper(II) acetate. A 'one-pot' reaction of the alpha,beta-diketo-ester equivalents 2 with amidrazones 1 in the presence of 2,5-norbornadiene 5 in boiling ethanol yielded the pyridines 4 and 2,2'-bipyridines 4 (R-1=2-pyridyl) directly without the need to isolate the corresponding triazines 3. Triazine 3c reacted with the aza-dienophiles 13 and 17 affording the products 16 and 18, respectively, in good yields. (C) 2008 Elsevier Ltd. All rights reserved.
• Synthesis of some 4,5-dihydroxypyrazoles
  作者：M. S. Khaikin、L. G. Fedorina、N. F. Rakova

  DOI：10.1007/bf00475230

  日期：1972.7
• VONTOR, TOMAS;PALAT, KAREL;ODLEROVA, ZELMIRA
  作者：VONTOR, TOMAS、PALAT, KAREL、ODLEROVA, ZELMIRA

  DOI：——

  日期：——