methyl 3-(2-benzyloxy-3-ethoxyphenyl)-3-hydroxy-2-methylenepropanoate | 515160-06-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: methyl 3-(2-benzyloxy-3-ethoxyphenyl)-3-hydroxy-2-methylenepropanoate
• 英文别名: Methyl 2-[(3-ethoxy-2-phenylmethoxyphenyl)-hydroxymethyl]prop-2-enoate
• CAS: 515160-06-2
• 化学式: C₂₀H₂₂O₅
• 分子量: 342.392
• InChiKey: JJMKJXSMAFPADG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3-(2-benzyloxy-3-ethoxyphenyl)-3-hydroxy-2-methylenepropanoate 在 盐酸 作用下， 以 乙酸酐 、 溶剂黄146 为溶剂， 以94%的产率得到3-(chloromethyl)-8-ethoxycoumarin
  参考文献：
  名称：

  A Convenient and Improved Baylis-Hillman Synthesis of 3-Substituted 2H-1-benzopyran-2-ones

  摘要：

  研究表明，使用 O-苄基水杨醛前体对巴利斯-希尔曼（Baylis-Hillman）产物进行卤酸催化脱保护和环化，可以化学选择性地获得 3-（卤甲基）香豆素（3-卤甲基-2H-1-苯并吡喃-2-酮），而且收率很高。

  DOI：

  10.1055/s-2002-35984
• 作为产物：
  描述：

  3-乙氧基水杨醛 在 三乙烯二胺 、 potassium carbonate 、 sodium iodide 作用下， 以 氯仿 、 丙酮 为溶剂， 生成 methyl 3-(2-benzyloxy-3-ethoxyphenyl)-3-hydroxy-2-methylenepropanoate
  参考文献：
  名称：

  A Convenient and Improved Baylis-Hillman Synthesis of 3-Substituted 2H-1-benzopyran-2-ones

  摘要：

  研究表明，使用 O-苄基水杨醛前体对巴利斯-希尔曼（Baylis-Hillman）产物进行卤酸催化脱保护和环化，可以化学选择性地获得 3-（卤甲基）香豆素（3-卤甲基-2H-1-苯并吡喃-2-酮），而且收率很高。

  DOI：

  10.1055/s-2002-35984

文献信息

• Application of Baylis–Hillman Methodology in the Synthesis of Coumarin Derivatives
  作者：Perry T. Kaye、M. A. Musa

  DOI：10.1081/scc-120018937

  日期：2003.1.6

  Abstract A general, chemoselective approach to 3-substituted coumarins via Baylis–Hillman reactions of O-benzylated salicylaldehyde precursors has been demonstrated. Competitive cyclization to chromene derivatives is inhibited by conjugate addition of benzylamine or piperidine to the α,β-unsaturated ester intermediates.

  摘要 已经证明了通过 O-苄基化水杨醛前体的 Baylis-Hillman 反应生成 3-取代香豆素的通用化学选择性方法。苄胺或哌啶与 α,β-不饱和酯中间体的共轭加成抑制了色烯衍生物的竞争性环化。
• Application of the acetate of baylis-hillman adducts of salicylaldehydes in the synthesis of methyl 2-oxo-2,3-dihydrobenzo[<i>b</i>]oxepine-4-carboxylates
  作者：Sang-Hyun Ahn、Hee Nam Lim、Kee-Jung Lee

  DOI：10.1002/jhet.5570450622

  日期：2008.11

  A simple synthesis of several methyl 2-oxo-2,3-dihydrobenzo[b]oxepine-4-carboxylates from Baylis-Hillman adducts of O-benzyl protected 2-hydroxybenzadehydes has been described through the acetylation, cyanation, debenzylation, as well as acid assisted Pinner cyclization.

  已经描述了通过乙酰化，氰化，脱苄基以及O-苄基保护的2-羟基苯甲醛的Baylis-Hillman加合物简单合成几种2-oxo-2,3-dihydrobenzo [ b ] oxepine-4-羧酸甲酯的方法。酸辅助的Pinner环化。
• Evaluation of Baylis–Hillman Routes to 3-(Aminomethyl)coumarin Derivatives
  作者：Idris Olasupo、Nathan R. Rose、Rosalyn Klein、Luqman A. Adams、Oluwole B. Familoni、Perry T. Kaye

  DOI：10.1080/00397911.2013.803575

  日期：2014.1.17

  The relative merits of two different Baylis-Hillman approaches toward the preparation of coumarin derivatives, containing peptide-like side chains, have been explored. In one approach, use of methyl acrylate as the activated alkene requires a protecting group strategy, an approach that is not necessary when using tert-butyl acrylate. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource(s): Full experimental and spectral details.]
• Synthesis of cinnamate ester–AZT conjugates as potential dual-action HIV-1 integrase and reverse transcriptase inhibitors
  作者：Temitope O. Olomola、Rosalyn Klein、Perry T. Kaye

  DOI：10.1016/j.tet.2014.09.045

  日期：2014.12

  Synthetic approaches to a series of novel cinnamate ester-AZT conjugates have been explored and a successful pathway has finally been developed. alpha-(Halomethyl)cinnamate esters, obtained in high yield by treating benzyl-protected salicylaldehde-derived Baylis-Hillman adducts with acetyl bromide at low temperature, have been treated with propargylamine to afford substrates for click chemistry reactions with azidothymidine (AZT) in the presence of in situ generated Cu(I) catalyst to produce the title compounds. (C) 2014 Elsevier Ltd. All rights reserved.