O-Ethoxycarbonyl-o-acetylphenol | 64042-56-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-Ethoxycarbonyl-o-acetylphenol
• 英文别名: (2-Acetylphenyl) ethyl carbonate
• CAS: 64042-56-4
• 化学式: C₁₁H₁₂O₄
• 分子量: 208.214
• InChiKey: WRORRGNSRGHEPM-UHFFFAOYSA-N

物化性质

• 沸点：
  262 °C
• 密度：
  1.147±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  O-Ethoxycarbonyl-o-acetylphenol 在 sodium tetrahydroborate 、 cerium(III) chloride heptahydrate 作用下， 以 乙醇 为溶剂， 反应 0.67h， 生成 乙基苯酚
  参考文献：
  名称：

  Deoxygenation of α,β-unsaturated acylphenols through ethyl o-acylphenylcarbonates with Luche reduction

  摘要：

  An efficient protocol for deoxygenation of alpha,beta-unsaturated acylphenols through ethyl o-acylphenylcarbonates with Luche reduction is described. The reaction shows very good selectivity and tolerates a wide range of functionalities on alpha,beta-unsaturated acylphenols, giving corresponding 2-allylphenols in good to excellent yields. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.02.109
• 作为产物：
  描述：

  乙醇 、 4-Methylidene-2H,4H-1,3-benzodioxin-2-one 生成 O-Ethoxycarbonyl-o-acetylphenol
  参考文献：
  名称：

  Lonsky,W.; Traitler,H., Chemische Berichte, 1977, vol. 110, p. 2601 - 2606

  摘要：

  DOI：

文献信息

• Shobana, N.; Amirthavalli, M.; Deepa, V., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 965 - 966
  作者：Shobana, N.、Amirthavalli, M.、Deepa, V.、Shanmugam, P.

  DOI：——

  日期：——
• Further developments in the synthesis of lamellarin alkaloids via direct metal–halogen exchange
  作者：Poonsakdi Ploypradith、Wiyada Jinaglueng、Chitkavee Pavaro、Somsak Ruchirawat

  DOI：10.1016/s0040-4039(02)02887-3

  日期：2003.2

  Direct metal-halogen exchange of 2-bromopyrrole carbonate derivatives with tert-butyllithium followed by the intramolecular lactonization of the resulting 2-pyrrole anion onto the carbonate provided the corresponding lamellarins in moderate to good yield. The lamellarin framework could be obtained from the direct metal-halogen exchange strategy in a 26-33% overall yield over 5-6 steps. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Utility of Polymer-Supported Reagents in the Total Synthesis of Lamellarins
  作者：Poonsakdi Ploypradith、Rachel Kirk Kagan、Somsak Ruchirawat

  DOI：10.1021/jo050388m

  日期：2005.6.1

  Four solid-supported reagents have been utilized in the multistep synthesis of lamellarins. The use of Amberlyst A-26 Br-3(-) and polymer bound pyridine hydrobromide perbromide (PVPHP) for keto alpha-bromination of the less studied ortho-substituted acetophenone derivatives selectively furnished the corresponding monobromination products (phenacyl bromide derivatives), which were used directly in condensation reactions with benzyldihydroisoquinoline mediated by Amberlyst A-26 NaCO3-. The 2H-pyrrole carbonates subsequently underwent intramolecular Friedel-Crafts transacylation followed by lactonization to provide the lamellarin skeleton. Alternatively, Amberlyst A-26 NaCO3- effectively served as base in condensation reaction of benzyldihydroisoquinoline with alpha-nitrocinnamate derivatives to provide the corresponding 2-ethoxycarbonyl pyrroles, which smoothly underwent O-debenzylation reaction followed by lactonization to furnish the lamellarin skeleton. The novel Amberlyst-15 mediated lactonization reactions effectively combined the otherwise two separate steps into a single transformation.
• SHOBANA, N.;MIRTHAVALLI, M. A.;DEEPA, V.;SHANMUGAM, P., INDIAN J. CHEM. B, 27,(1988) N0, C. 965-966
  作者：SHOBANA, N.、MIRTHAVALLI, M. A.、DEEPA, V.、SHANMUGAM, P.

  DOI：——

  日期：——
• LONSKY W.; TRAITLER H., CHEM. BER. <CHBE-AM>, 1977, 110, NO 7, 2601-2606
  作者：LONSKY W.、 TRAITLER H.

  DOI：——

  日期：——