methyl 3-<2-(5-methylfuryl)>-3-hydroxy-2-methylenepropanoate | 124575-70-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: methyl 3-<2-(5-methylfuryl)>-3-hydroxy-2-methylenepropanoate
• 英文别名: methyl 2-[5-methylfuran-2-yl(hydroxy)methyl]prop-2-enoate；Methyl 2-[hydroxy-(5-methylfuran-2-yl)methyl]prop-2-enoate
• CAS: 124575-70-8
• 化学式: C₁₀H₁₂O₄
• 分子量: 196.203
• InChiKey: KWWOBKATYIHDBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3-<2-(5-methylfuryl)>-3-hydroxy-2-methylenepropanoate 在 N-溴代丁二酰亚胺(NBS) 、 sodium acetate 、 碳酸氢钠 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.08h， 以71.429%的产率得到
  参考文献：
  名称：

  Sequential Morita–Baylis–Hillman/Achmatowicz reactions: an expeditious access to pyran-3(6H)-ones with a unique substitution pattern

  摘要：

  We herein disclosed a novel approach to synthesize densely functionalized 6-hydroxy-2H-pyran-3(6H)-ones with moderate to good diastereoselectivity. The method is based on a two step sequence using Morita-Baylis-Hillman adducts as substrates for the Achmatowicz rearrangement, allowing the preparation of highly substituted pyran-3-ones with overall yields ranging from 17% to 80% and a unique substitution pattern. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.09.120
• 作为产物：
  描述：

  5-甲基呋喃醛 、 丙烯酸甲酯（MA） 在 三乙烯二胺 、 溶剂黄146 作用下， 以 neat (no solvent) 为溶剂， 反应 20.0h， 以84%的产率得到methyl 3-<2-(5-methylfuryl)>-3-hydroxy-2-methylenepropanoate
  参考文献：
  名称：

  Morita-Baylis-Hillman 反应的改进协议允许前所未有的广泛合成范围

  摘要：

  通过在无溶剂条件下将 DABCO 和乙酸结合，活化和未活化醛的 Morita-Baylis-Hillman 反应速率均显着提高。所公开的程序操作简单并且与多种亲核和亲电反应伙伴相容。

  DOI：

  10.1002/ejoc.202101448

文献信息

• Drewes, S. E.; Emslie, N. D.; Khan, A. A., Synthetic Communications, 1989, vol. 19, # 5and6, p. 959 - 964
  作者：Drewes, S. E.、Emslie, N. D.、Khan, A. A.、Roos, G. H. P.

  DOI：——

  日期：——
• DREWES, S. E.;EMSLIE, N. D.;KHAN, A. A.;ROOS, G. H. P., SYNTH. COMMUN., 19,(1989) N-6, C. 959-964
  作者：DREWES, S. E.、EMSLIE, N. D.、KHAN, A. A.、ROOS, G. H. P.

  DOI：——

  日期：——
• Sequential Morita–Baylis–Hillman/Achmatowicz reactions: an expeditious access to pyran-3(6H)-ones with a unique substitution pattern
  作者：Bruno B. Guidotti、Fernando Coelho

  DOI：10.1016/j.tetlet.2015.09.120

  日期：2015.11

  We herein disclosed a novel approach to synthesize densely functionalized 6-hydroxy-2H-pyran-3(6H)-ones with moderate to good diastereoselectivity. The method is based on a two step sequence using Morita-Baylis-Hillman adducts as substrates for the Achmatowicz rearrangement, allowing the preparation of highly substituted pyran-3-ones with overall yields ranging from 17% to 80% and a unique substitution pattern. (C) 2015 Elsevier Ltd. All rights reserved.
• An Improved Protocol for the Morita‐Baylis‐Hillman Reaction Allows Unprecedented Broad Synthetic Scope
  作者：Nilton S. Camilo、Hugo Santos、Lucas A. Zeoly、Fábio S. Fernandes、Manoel T. Rodrigues、Thiago S. Silva、Samia R. Lima、José Cláudio Serafim、Aline S. B. de Oliveira、Arthur G. Carpanez、Giovanni W. Amarante、Fernando Coelho

  DOI：10.1002/ejoc.202101448

  日期：2022.3.7

  By the combination of DABCO and acetic acid under solvent-free conditions, the Morita-Baylis-Hillman reaction rate of both activated and non-activated aldehydes increased significantly. The disclosed procedure is operationally simple and is compatible with a wide array of both nucleophilic and electrophilic reaction partners.

  通过在无溶剂条件下将 DABCO 和乙酸结合，活化和未活化醛的 Morita-Baylis-Hillman 反应速率均显着提高。所公开的程序操作简单并且与多种亲核和亲电反应伙伴相容。