methyl 5-hydroxy-5-(4-methoxyphenyl)-3-oxopentanoate | 133810-03-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: methyl 5-hydroxy-5-(4-methoxyphenyl)-3-oxopentanoate
• CAS: 133810-03-4
• 化学式: C₁₃H₁₆O₅
• 分子量: 252.267
• InChiKey: LZOCNRQPKNUXPA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 5-hydroxy-5-(4-methoxyphenyl)-3-oxopentanoate 在 4-乙酰氨基苯磺酰叠氮 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以80%的产率得到methyl 2-diazo-5-hydroxy-5-(4-methoxyphenyl)-3-oxopentanoate
  参考文献：
  名称：

  A short and convenient strategy for the synthesis of pyridazines via Diaza–Wittig reaction

  摘要：

  A convenient and selective synthesis of 6-substituted-4-hydroxy-3-methoxycarbonyl pyridazines has been developed via a diaza-Wittig reaction. The desired products substituted at the C6 position can be obtained from readily available starting materials under mild conditions. This represents an attractive new method for the synthesis of pyridazine derivatives. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.09.059
• 作为产物：
  描述：

  甲醇 以71%的产率得到
  参考文献：
  名称：

  ABE, KOJI;TAKAHASHI, SENJI;MORI, NOBUO, CHEM. EXPRESS, 6,(1991) N, C. 193-195

  摘要：

  DOI：

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。
• A Chemoenzymatic Approach to Optically Active 5-Hydroxy-3-oxo-carboxylates
  作者：Chengye Yuan、Chengfu Xu、Yonghui Zhang

  DOI：10.1055/s-2004-817746

  日期：——

  Enzymatic hydrolysis was applied to the preparation of certain chiral 5-hydroxy-3-oxo-carboxylates that are potential precursors for natural product synthesis via the formation of lactone derivatives and tetrahydropyran rings.

  酶促水解被应用于某些手性5-羟基-3-氧基羧酸酯的制备，这些化合物是通过形成内酯衍生物和四氢吡喃环用于天然产物合成的潜在前体。
• 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。
• ——
  作者：I. P. Lokot'、F. S. Pashkovskii、F. A. Lakhvich

  DOI：10.1023/a:1011913328785

  日期：——
• Synthesis of multifunctionalized building blocks via vinylogous addition of Chan’s diene to carbonyl and carbonyl-related electrophiles, mediated by molecular iodine
  作者：Rosaria Villano、Maria R. Acocella、Arrigo Scettri

  DOI：10.1016/j.tet.2011.02.036

  日期：2011.4

  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.