5-(hydroxy(4-tolyl)methyl)furan-2(5H)-one

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-(hydroxy(4-tolyl)methyl)furan-2(5H)-one
• 英文别名: 5-((hydroxy)(p-tolyl)methyl)furan-2(5H)-one；5-(hydroxy(phenyl)methyl)furan-2(5H)-one；(2S)-2-[(R)-hydroxy-(4-methylphenyl)methyl]-2H-furan-5-one
• 化学式: C₁₂H₁₂O₃
• 分子量: 204.225
• InChiKey: COERKSMASSYPHH-CMPLNLGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (2S)-2-[(R)-(4-methylphenyl)-trimethylsilyloxymethyl]-2H-furan-5-one 在 盐酸 作用下， 以 乙醚 为溶剂， 以100%的产率得到5-(hydroxy(4-tolyl)methyl)furan-2(5H)-one
  参考文献：
  名称：

  Iodine as a mild and efficient catalyst for the diastereoselective synthesis of δ-silyloxy-γ-lactones

  摘要：

  Aldehydes undergo smooth nucleophilic addition with 2-trimethylsilyloxyfuran in the presence of 10 mol % of iodine under mild and neutral conditions to produce the corresponding 6-silyloxy-alpha,beta-unsaturated-gamma-lactones in high yields and with moderate diastereoselectivity. ortho-Substituted benzaldehydes afford the syn-isomer predominantly. The use of iodine makes this procedure quite simple, more convenient and cost-effective. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2008.07.085

文献信息

• Diastereoselective Mukaiyama Aldol Reaction of 2-(Trimethylsilyloxy)furan Catalyzed by Bismuth Triflate
  作者：Thierry Ollevier、Jean-Emmanuel Bouchard、Valerie Desyroy

  DOI：10.1021/jo702085p

  日期：2008.1.1

  We have developed an efficient vinylogous Mukaiyama aldol reaction of 2-(trimethylsilyloxy)furan with various aromatic aldehydes mediated by bismuth triflate in low catalyst loading (1 mol %). The reaction proceeds rapidly and affords the corresponding 5-(hydroxy(aryl)methyl)furan-2(5H)-ones in high yields with good to very good diastereoselectivities (dr up to >98:2). Such selectivities, albeit previously

  我们已经开发了在低催化剂负载量（1 mol％）下2-（三甲基甲硅烷氧基）呋喃与三氟甲磺酸铋介导的各种芳族醛的高效乙烯树脂Mukaiyama aldol反应。反应迅速进行并以高收率提供良好的至非常好的非对映选择性（dr高达> 98：2）的相应5-（羟基（芳基）甲基）呋喃-2（5 H）-酮。尽管以前用其他路易斯酸报道过，但这种选择性可以用低得多的催化剂负载量来实现。还可以以良好的非对映选择性获得衍生自酮的5-（羟基（烷基）甲基）呋喃-2（5 H）-1 。
• N-Heterocyclic Carbene Catalyzed Vinylogous Aldol Reaction of 2-(Trimethylsilyloxy)furan and Aldehydes
  作者：Lin He、Guang-Fen Du、Cheng-Zhi Gu、Bin Dai

  DOI：10.1055/s-0030-1258551

  日期：2010.10

  A N-Heterocyclic carbenes (NHC) catalyzed vinylogous aldol reaction between 2-(trimethylsilyloxy)furan and aldehydes has been developed, providing γ-substituted butenolides in high yields with good diastereoselectivities. Furthermore, the catalyst loading can be reduced to 1 mol%.

  一种N-杂环卡宾（NHC）催化的2-（三甲基硅氧基）呋喃与醛的乙烯式醇醛反应已经开发出来，能够在高产率和良好的非对映选择性下提供γ-取代的丁烯内酯。此外，催化剂负载量可降至1摩尔%。
• Diastereoselective Synthesis of <font>γ</font>-Butenolides Catalyzed by Potassium <i>tert</i>-Butoxide
  作者：Guang-Fen Du、Lin He、Cheng-Zhi Gu、Bin Dai

  DOI：10.1080/00397911.2010.538888

  日期：2012.4.15

  Abstract Potassium tert-butoxide (0.1 mol%) catalyzed a vinylogous Mukaiyama aldol reaction between aromatic and aliphatic aldehydes with 2-(trimethylsilyloxy)furan. The corresponding γ-butenolides were obtained in good yields with good diastereoselectivities. GRAPHICAL ABSTRACT

  摘要 叔丁醇钾 (0.1 mol%) 催化芳香醛和脂肪醛与 2-（三甲基甲硅烷氧基）呋喃之间的乙烯基 Mukaiyama 羟醛反应。以良好的收率和良好的非对映选择性获得了相应的γ-丁烯内酯。图形概要
• 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。
• Asymmetric Direct Vinylogous Aldol Reaction of Unactivated γ-Butenolide to Aldehydes
  作者：Yang Yang、Ke Zheng、Jiannan Zhao、Jian Shi、Lili Lin、Xiaohua Liu、Xiaoming Feng

  DOI：10.1021/jo100946d

  日期：2010.8.6

  The asymmetric direct vinylogous aldol reaction of unactivated γ-butenolide with aldehydes has been developed, giving the corresponding 5-(1′-hydroxy)butenolide derivatives in high yields (up to 93%) and enantioselectivities (up to 83% ee) under mild conditions.

  已开发出未活化的γ-丁烯内酯与醛类的不对称直接乙烯基醛醇缩合反应，可在温和的条件下以高收率（高达93％）和对映选择性（高达83％ee）提供相应的5-（1'-羟基）丁烯醇内酯衍生物。情况。