(S)-5-((S)-(4-bromophenyl)(hydroxy)methyl)furan-2(5H)-one | 1252614-20-2

• 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: (S)-5-((S)-(4-bromophenyl)(hydroxy)methyl)furan-2(5H)-one
• 英文别名: 5-((4-bromophenyl)(hydroxy)methyl)furan-2(5H)-one；(2S)-2-[(S)-(4-bromophenyl)-hydroxymethyl]-2H-furan-5-one
• CAS: 1252614-20-2
• 化学式: C₁₁H₉BrO₃
• 分子量: 269.095
• InChiKey: SOWRMERSZFOZBR-ONGXEEELSA-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：

  2(5H)-呋喃酮 、 对溴苯甲醛 在 C₃₇H₃₈F₉N₅O₅S 作用下， 以 乙醚 为溶剂， 反应 48.0h， 以94%的产率得到
  参考文献：
  名称：

  方酸-磺酰胺有机催化剂用于不对称直接乙烯基醛醇缩合反应

  摘要：

  呋喃-2（5 H）-one与醛的不对称直接乙烯基醇醛缩合反应，在催化量的新型方酰胺-磺酰胺有机催化剂的存在下，导致相应的加成产物具有高到极好的对映选择性。这是第一个成功的报告，阐明了使用方酸酰胺-磺酰胺有机催化剂进行高度立体选择性反应的一个例子。

  DOI：

  10.1021/acs.joc.7b00287

文献信息

• Silicon tetrachloride in organic synthesis: new applications for the vinylogous aldol reaction
  作者：Maria R. Acocella、Margherita De Rosa、Antonio Massa、Laura Palombi、Rosaria Villano、Arrigo Scettri

  DOI：10.1016/j.tet.2005.02.020

  日期：2005.4

  efficient methodology for vinylogous aldol reactions based on SiCl4 catalysis. According to the nucleophilicity Mayr's scale, vinylogous aldol reaction of Chan's diene proved to be effective by using catalytic amount of SiCl4, without any other promoter. On the contrary, the SiCl4/Lewis base system has been conveniently exploited for the efficient and selective vinylogous reaction of less nucleophilic

  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。
• 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。
• Organocatalytic asymmetric direct vinylogous aldol reactions of γ-crotonolactone with aromatic aldehydes
  作者：Sunil V. Pansare、Eldho K. Paul

  DOI：10.1039/c0cc04191b

  日期：——

  The direct aldol reaction of γ-crotonolactone and various aromatic aldehydes is catalyzed by bifunctional aminothiourea and aminosquaramide organocatalysts to provide diastereomerically and enantiomerically enriched 5-substituted 2(5H) furanones (γ-butenolides). The reaction is a simple alternative to the classical vinylogous aldol reaction of silyloxy furans.

  双功能氨基硫脲和氨基方酰胺有机催化剂催化γ-巴豆酸内酯和各种芳香醛的直接羟醛反应，提供非对映体和对映体富集的5-取代2(5H)呋喃酮（γ-丁烯内酯）。该反应是甲硅烷氧基呋喃的经典插烯羟醛反应的简单替代反应。
• 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.