ethyl 2-acetoxy-2-chloro-3-oxo-3-phenylpropanoate | 865445-60-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-acetoxy-2-chloro-3-oxo-3-phenylpropanoate
• 英文别名: Ethyl 2-acetyloxy-2-chloro-3-oxo-3-phenylpropanoate
• CAS: 865445-60-9
• 化学式: C₁₃H₁₃ClO₅
• 分子量: 284.696
• InChiKey: LDZJWLUDUVBKSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 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-2-chloro-3-oxo-3-phenylpropanoate 在 甲胺 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成 ethyl 2,3-dioxo-3-phenylpropanoate
  参考文献：
  名称：

  高度取代的咪唑衍生物的便捷合成

  摘要：

  摘要 已开发出由 α-乙酰氧基-α-氯-β-酮酯、醛和乙酸铵一锅法合成三取代咪唑衍生物的方法。图形概要

  DOI：

  10.1080/00397911.2011.591957
• 作为产物：
  描述：

  ethyl 2-acetoxy-3-oxo-3-phenylpropanoate 在 磺酰氯 作用下， 以 二氯甲烷 为溶剂， 以77%的产率得到ethyl 2-acetoxy-2-chloro-3-oxo-3-phenylpropanoate
  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

• A convenient synthesis of substituted 2,2′:6′,2″-terpyridines
  作者：Alexander Gehre、Stephen P. Stanforth、Brian Tarbit

  DOI：10.1016/j.tetlet.2008.05.128

  日期：2008.8

  The 2,2′:6′,2″-terpyridines 8a and 8b were prepared in good yield by reacting α-acetoxy-α-chloro-β-keto-esters 1 (R1 = nPr and Ph) with the bis-amidrazone 7 and 2,5-norbornadiene 5 in ethanol at reflux.

  的2,2'：6'，2“-terpyridines图8a和图8b分别以良好的收率由α乙酸基α氯β酮酯反应制备1（R 1  =  Ñ Pr和PH）与双-乙醇中的dra胺7和2,5-降冰片二烯5回流。
• 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.