5-((4-bromophenyl)(hydroxy)methyl)furan-2(5H)-one | 1233510-46-7

• 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-((4-bromophenyl)(hydroxy)methyl)furan-2(5H)-one
• 英文别名: (2S)-2-[(R)-(4-bromophenyl)-hydroxymethyl]-2H-furan-5-one
• CAS: 1233510-46-7
• 化学式: C₁₁H₉BrO₃
• 分子量: 269.095
• InChiKey: SOWRMERSZFOZBR-GXSJLCMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  三甲硅氧基-2-呋喃 、 对溴苯甲醛 在 四氯化硅 、 二甲基亚砜 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 5-((4-bromophenyl)(hydroxy)methyl)furan-2(5H)-one 、 (S)-5-((S)-(4-bromophenyl)(hydroxy)methyl)furan-2(5H)-one
  参考文献：
  名称：

  四氯化硅在有机合成中的应用：乙烯醇醛醇缩醛反应的新应用

  摘要：

  本文介绍了一种基于SiCl 4催化的乙烯基醇醛醇缩醛反应的新颖而有效的方法。根据亲核性迈尔（Mayr）规模，通过使用催化量的SiCl 4而不使用任何其他助催化剂，证明了陈氏二烯的乙烯基醇醛醇缩醛反应是有效的。相反，SiCl 4 / Lewis碱系统已被方便地用于较少亲核的Danishefsky's二烯和2-三甲基甲硅烷基氧基呋喃（TMSOF）的高效选择性乙烯基反应。实际上，许多路易斯碱（例如亚砜，甲酰胺和磷酰胺）已成功用作SiCl 4发起人。由2,2,6-三甲基-[1,3]-二恶英-4-酮衍生物衍生而来的TMSOF和甲硅烷基氧二烯需要化学计量的SiCl 4，而Chan和Danishefsky的二烯的乙烯基醇醛缩合反应在存在催化或亚化学计量的催化剂。

  DOI：

  10.1016/j.tet.2005.02.020

文献信息

• Asymmetric Vinylogous Aldol Reaction of Silyloxy Furans with a Chiral Organic Salt
  作者：Ravi P. Singh、Bruce M. Foxman、Li Deng

  DOI：10.1021/ja103331t

  日期：2010.7.21

  significance there is a general lack of asymmetric vinylogous aldol reactions that tolerate variations of both the silyloxy furans and aldehydes. We have developed a new chiral organic catalyst based on a carboxylate-ammonium salt prepared from a thiourea-amine and a carboxylic acid. This new catalyst enabled us to develop an efficient asymmetric vinylogous aldol reaction of unprecedented scope with respect

  尽管它们具有合成意义，但普遍缺乏耐受甲硅烷氧基呋喃和醛变化的不对称乙烯基醛醇反应。我们开发了一种基于由硫脲胺和羧酸制备的羧酸铵盐的新型手性有机催化剂。这种新催化剂使我们能够针对 2-三甲基甲硅烷氧基呋喃和醛，开发出范围空前的高效不对称乙烯基醛醇反应。
• 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。
• Uncatalyzed, Diastereoselective Vinylogous Mukaiyama Aldol Reactions on Aqueous Media: Pyrrole vs Furan 2-Silyloxy Dienes
  作者：Claudio Curti、Lucia Battistini、Franca Zanardi、Gloria Rassu、Vincenzo Zambrano、Luigi Pinna、Giovanni Casiraghi

  DOI：10.1021/jo101799e

  日期：2010.12.17

  diastereoselective vinylogous Mukaiyama aldol reaction is reported, between pyrrole/furan-based dienoxy silanes and aromatic aldehydes on salty water/methanol medium, at almost human body temperature, under ultrasonic irradiation. With pyrrole dienes the reaction is anti-selective, while that of furan dienes is syn-selective. The dual role of water as both reaction medium and promoter is highlighted.

  据报道，在超声波辐射下，几乎在人体温度下，在咸水/甲醇介质中，吡咯/呋喃基二烯氧基硅烷与芳族醛之间发生了第一个未催化的非对映选择性乙烯基Mukaiyama aldol反应。对于吡咯二烯，反应是反选择性的，而呋喃二烯的反应是顺选择性的。强调了水作为反应介质和促进剂的双重作用。
• Highly enantioselective vinylogous addition of 2-trimethylsilyloxyfuran to aldehydes promoted by the SiCl4/chiral Lewis base system
  作者：Laura Palombi、Maria R. Acocella、Nicoletta Celenta、Antonio Massa、Rosaria Villano、Arrigo Scettri

  DOI：10.1016/j.tetasy.2006.11.041

  日期：2006.12

  This paper reports the regio-, diastereo- and highly enantioselective vinylogous aldol reaction of 2-trimethylsilyloxyfuran (TMSOF) promoted by the SiCl4/Lewis base catalytic system. Several electron-pair donors proved to be effective as SiCl4 activators versus the TMSOF gamma-selective addition to aldehydes giving rise to different diastereoisomeric ratios, while Denmark's chiral bis-phosphoramide (R,R)-7 gave the highest enantioselectivity for both the anti- and syn-diastereoisomers. Furthermore, by using ambident electrophiles such as alpha,beta-unsaturated aldehydes, the SiCl4/Lewis base-promoted process leads exclusively to the 1,2-addition products. (c) 2006 Elsevier Ltd. All rights reserved.