4-[(1-hydroxy-1-(4-methoxyphenyl)methyl)]-2-buten-4-olide | 475232-65-6

• 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-(4-methoxyphenyl)methyl)]-2-buten-4-olide
• 英文别名: 5-[hydroxy(4-methoxyphenyl)methyl]furan-2(5H)one；2-[hydroxy-(4-methoxyphenyl)methyl]-2H-furan-5-one
• CAS: 475232-65-6
• 化学式: C₁₂H₁₂O₄
• 分子量: 220.225
• InChiKey: VOYHJCYSELBSQX-UHFFFAOYSA-N

物化性质

• 沸点：
  453.5±35.0 °C(Predicted)
• 密度：
  1.294±0.06 g/cm3(Predicted)

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

• 作为反应物：
  描述：

  4-[(1-hydroxy-1-(4-methoxyphenyl)methyl)]-2-buten-4-olide 在 H-ZSM-5 zeolite 作用下， 以 苯 为溶剂， 反应 12.0h， 以90.8%的产率得到(Z)-4-(4-methoxybenzylidene)-2-butenolide
  参考文献：
  名称：

  ZEOLITE MEDIATED STEREOSELECTIVE SYNTHESIS OF γ-ALKYLIDENEBUTENOLIDES

  摘要：

  Stereoselective synthesis of Z-gamma-alkylidenebutenolides has been achieved through H-ZSM 5 mediated dehydration.

  DOI：

  10.1081/scc-120004083
• 作为产物：
  描述：

  2(5H)-呋喃酮 、 4-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68%的产率得到4-[(1-hydroxy-1-(4-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。
• Organocatalyzed Highly Enantioselective and anti-Selective Construction of γ-Butenolides through Vinylogous Mukaiyama Aldol Reaction
  作者：Ning Zhu、Bao-Chun Ma、Yong Zhang、Wei Wang

  DOI：10.1002/adsc.201000099

  日期：——

  The formation of chiral γ‐butenolides has been achieved with good yields (up to 90%), high enantioselectivity (up to 91%) and diastereoselectivity (up to 9/1, anti‐selective) through an organocatalyzed vinylogous Mukaiyama aldol reaction of 2‐(trimethylsilyloxy)furan and aldehydes. A wide range of chiral γ‐butenolides was obtained under mild conditions by this methodology.

  通过2的有机乙烯基乙烯基Mukaiyama醇醛醇醛缩醛反应2可以形成高收率（高达90％），高对映选择性（高达91％）和非对映选择性（高达9/1，抗选择性）的手性γ-丁烯内酯。 -（三甲基甲硅烷氧基）呋喃和醛。通过这种方法，在温和的条件下获得了广泛的手性γ-丁烯内酯。
• The first organocatalytic addition of 2-trimethylsilyloxyfuran to carbonyl compounds: hydrogen-bond catalysis in γ-butenolides synthesis
  作者：Margherita De Rosa、Lucia Citro、Annunziata Soriente

  DOI：10.1016/j.tetlet.2006.09.143

  日期：2006.11

  This letter describes the first example of diastereoselective 'organocatalyzed' synthesis of the butenolide products substituted at the gamma-position by a chain bearing hydroxyl groups. The urea-derivative 4 has proved to be an efficient catalyst for the addition of the commercial TMSOF to carbonyl compounds under solvent-free conditions. The reaction conditions and generality of the procedure have been examined. (c) 2006 Elsevier Ltd. All rights reserved.
• 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.
• ZEOLITE MEDIATED STEREOSELECTIVE SYNTHESIS OF γ-ALKYLIDENEBUTENOLIDES
  作者：N. Sundar、Mrinal K. Kundu、P. Veera Reddy、G. Mahendra、Sujata V. Bhat

  DOI：10.1081/scc-120004083

  日期：2002.1.1

  Stereoselective synthesis of Z-gamma-alkylidenebutenolides has been achieved through H-ZSM 5 mediated dehydration.