4-[(1-hydroxy-1-(3-methoxyphenyl)methyl)]-2-buten-4-olide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-[(1-hydroxy-1-(3-methoxyphenyl)methyl)]-2-buten-4-olide
• 英文别名: 2-[hydroxy-(3-methoxyphenyl)methyl]-2H-furan-5-one
• 化学式: C₁₂H₁₂O₄
• 分子量: 220.225
• InChiKey: OPXQELFMSUTOAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2(5H)-呋喃酮 、 3-甲氧基苯甲醛 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以73%的产率得到4-[(1-hydroxy-1-(3-methoxyphenyl)methyl)]-2-buten-4-olide
  参考文献：
  名称：

  γ-Regioselectivity of lithiated 2-buten-4-olide towards aromatic aldehydes: a simple synthesis of γ-arylidenebutenolides

  摘要：

  Lithiated 2-buten-4-olide was found to react with aromatic aldehydes regioselectively at gamma-position to provide 4-(1-aryl-1-hydroxymethyl)-2-buten-4-olides which could be readily converted into the corresponding (Z)-gamma-arylidenebutenolides. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00669-3

文献信息

• Catalytic, Enantioselective Vinylogous Mukaiyama Aldol Reaction of Furan-Based Dienoxy Silanes: A Chemodivergent Approach to γ-Valerolactone Flavan-3-ol Metabolites and δ-Lactone Analogues
  作者：Claudio Curti、Nicoletta Brindani、Lucia Battistini、Andrea Sartori、Giorgio Pelosi、Pedro Mena、Furio Brighenti、Franca Zanardi、Daniele Del Rio

  DOI：10.1002/adsc.201500705

  日期：2015.12.14

  a set of hydroxyphenyl γ-valerolactones was achieved starting from 2-silyloxyfuran and alkoxy-substituted benzaldehydes as common precursors. Key synthesis steps included an enantioselective vinylogous Mukaiyama aldol reaction and a Barton–McCombie deoxygenation. Five enantioenriched γ-valerolactone targets were obtained in 5–6 steps, 18–63% overall yields and 82–98 % ee, paving the way for the straightforward

  从2-甲硅烷氧基呋喃和烷氧基取代的苯甲醛作为常见的前体开始，实现了一组羟苯基γ-戊内酯的不对称合成。关键的合成步骤包括对映选择性的乙烯基Mukaiyama aldol反应和Barton-McCombie脱氧反应。通过5–6个步骤获得了5个对映体富集的γ-戊内酯目标，总产率为18–63％，ee为82–98％，这为直接进入此类具有生物有效性且难得的flavan -3-ol代谢物铺平了道路。同时，偶然发现了一种空前的一锅还原环扩展过程，从酚丁醇化物前体产生外消旋的δ-内酯类似物。
• γ-Regioselectivity of lithiated 2-buten-4-olide towards aromatic aldehydes: a simple synthesis of γ-arylidenebutenolides
  作者：Manat Pohmakotr、Patoomratana Tuchinda、Pornchai Premkaisorn、Vichai Reutrakul

  DOI：10.1016/s0040-4020(98)00669-3

  日期：1998.9

  Lithiated 2-buten-4-olide was found to react with aromatic aldehydes regioselectively at gamma-position to provide 4-(1-aryl-1-hydroxymethyl)-2-buten-4-olides which could be readily converted into the corresponding (Z)-gamma-arylidenebutenolides. (C) 1998 Elsevier Science Ltd. All rights reserved.