Methyl-(E)-5-hydroxy-3-oxo-7-phenylhept-6-enoate | 55848-86-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: Methyl-(E)-5-hydroxy-3-oxo-7-phenylhept-6-enoate
• 英文别名: methyl 5-hydroxy-3-oxo-7-phenyl-6-heptenoate；Methyl 7-phenyl-5-hydroxy-3-oxo-6-heptenoate；methyl 5-hydroxy-3-oxo-7-phenylhept-6-enoate
• CAS: 55848-86-7
• 化学式: C₁₄H₁₆O₄
• 分子量: 248.279
• InChiKey: CUHUZWHBAOVDHS-UHFFFAOYSA-N

物化性质

• 沸点：
  436.1±45.0 °C(Predicted)
• 密度：
  1.174±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Methyl-(E)-5-hydroxy-3-oxo-7-phenylhept-6-enoate 在 lithium aluminium tetrahydride 、 四氯化钛 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 生成 syn-5-cinnamoyl-1,3,5-pentanetriol 、 anti-5-cinnamoyl-1,3,5-pentanetriol
  参考文献：
  名称：

  Bonini, Carlo; Bianco, Armandodoriano; Fabio,Romano Di, Gazzetta Chimica Italiana, 1991, vol. 121, # 2, p. 75 - 80

  摘要：

  DOI：
• 作为产物：
  描述：

  1,3-bis(trimethylsiloxy)-1-methoxybuta-1,3-diene 、 肉桂醛 在 碘 、 三氟乙酸 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 0.02h， 以97%的产率得到Methyl-(E)-5-hydroxy-3-oxo-7-phenylhept-6-enoate
  参考文献：
  名称：

  Synthesis of multifunctionalized building blocks via vinylogous addition of Chan’s diene to carbonyl and carbonyl-related electrophiles, mediated by molecular iodine

  摘要：

  The synthesis of multifunctionalized beta-ketoesters has been achieved by using molecular iodine as a catalyst under very mild conditions. The vinylogous addition of Chan's diene 1 to carbonyl and carbonyl-related compounds (aldehydes, ketones, imines and acetals) occurred with high efficiencies and with complete gamma-selectivity, giving a useful method for the synthesis of interesting libraries of different delta-functionalized beta-ketoesters. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.02.036

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。
• Study on an Aldol Reaction Catalyzed by Ti(IV)/Calix[n]arene Complexes
  作者：Annunziata Soriente、Margherita De Rosa、Marina Fruilo、Laura Lepore、Carmine Gaeta、Placido Neri

  DOI：10.1002/adsc.200505023

  日期：2005.5

  Ti(IV)/calixarene complexes, formed in situ or previously prepared with standard procedures, can be conveniently used as efficient catalysts in the aldol reaction of Chan's silyloxydiene with a range of aldehydes bearing either activating or deactivating groups, including aromatic, heteroaromatic and α,β-unsaturated ones. The structure of both calixarene ligand and aldehyde, as well as the reaction

  原位形成或预先用标准方法制备的Ti（IV）/杯芳烃络合物可方便地用作Chan的甲硅烷氧基二烯与一系列带有活化或失活基团的醛（包括芳族，杂芳族和α）的醛的醛醇缩合反应中的高效催化剂，β-不饱和的。杯芳烃配体和醛的结构以及反应条件强烈影响反应效率。NMR实验和实验结果表明，原位制备的Ti（IV）/杯芳烃系统中催化物种的结构在很大程度上取决于所采用的浓度和温度。
• A CONVENIENT METHOD FOR THE PREPARATION OF δ-HYDROXY-β-KETOESTERS AND 6-ALKYL-5,6-DIHYDRO-4-HYDROXY-2-PYRONES. APPLICATION TO THE SYNTHESES OF KAWAIN AND DIHYDROKAWAIN
  作者：Toshio Izawa、Teruaki Mukaiyama

  DOI：10.1246/cl.1975.161

  日期：1975.2.5

  The hydroxyketoesters[3] were easily lactonized to the corresponding lactones[4] in excellent yields by the hydrolysis with aqueous alkali, followed by acidification. The present method was successfully applied to the syntheses of dihydrokawain[7c] and kawain[7d].

  δ-羟基-β-酮酯[3] 和 6-烷基-5, 6-二氢-4-羟基-2-吡喃酮[4] 通过 TiCl4 促进的双烯酮 [1] 与各种醛的加成获得 [4]。 2]，然后用酒精处理。通过用碱水溶液水解，然后酸化，羟基酮酯 [3] 很容易内酯化为相应的内酯 [4]，收率极好。该方法已成功应用于二氢卡哇因[7c]和卡哇因[7d]的合成。
• Process for the preparation of derivatives of 3,5-dihydroxypentanoic acid
  申请人：Rhone-Poulenc Rorer S.A.

  公开号：US05347039A1

  公开（公告）日：1994-09-13

  This invention is directed to a method for stereoselectively preparing a syn-dihydroxylated compound comprising reacting a 3-hydroxyket-1-one with a borohydride in the presence of titanium derivative.

  本发明涉及一种立体选择性制备合成二羟基化合物的方法，包括在钛衍生物的存在下，将3-羟基酮-1与硼氢化物反应。
• Bonini, Carlo; Bianco, Armandodoriano; Fabio,Romano Di, Gazzetta Chimica Italiana, 1991, vol. 121, # 2, p. 75 - 80
  作者：Bonini, Carlo、Bianco, Armandodoriano、Fabio,Romano Di、Mecozzi, Sandro、Proposito, Alessandro、Righi, Giuliana

  DOI：——

  日期：——