5-(4-Fluoro-phenyl)-5-hydroxy-3-oxo-pentanoic acid methyl ester | 682770-47-4

• 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-Fluoro-phenyl)-5-hydroxy-3-oxo-pentanoic acid methyl ester
• 英文别名: Methyl 5-(4-fluorophenyl)-5-hydroxy-3-oxopentanoate
• CAS: 682770-47-4
• 化学式: C₁₂H₁₃FO₄
• 分子量: 240.231
• InChiKey: QHOQFXJWYKVJFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-(4-Fluoro-phenyl)-5-hydroxy-3-oxo-pentanoic acid methyl ester 在 4-二甲氨基吡啶 、 水 、 N,N'-二环己基碳二亚胺 、 磷脂酶B 作用下， 以 二氯甲烷 、 异丙醚 为溶剂， 反应 24.0h， 生成 (5S) methyl δ-butyryloxy-δ-(p-fluorophenyl)-β-oxo-pentanoate
  参考文献：
  名称：

  A Chemoenzymatic Approach to Optically Active 5-Hydroxy-3-oxo-carboxylates

  摘要：

  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。

  DOI：

  10.1055/s-2004-817746
• 作为产物：
  描述：

  1,3-bis(trimethylsiloxy)-1-methoxybuta-1,3-diene 、 对氟苯甲醛 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99%的产率得到5-(4-Fluoro-phenyl)-5-hydroxy-3-oxo-pentanoic acid methyl ester
  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

• 一种3-羰基5-羟基酯类化合物的合成方法
  申请人：温州大学新材料与产业技术研究院

  公开号：CN112851513B

  公开（公告）日：2022-10-28

  本发明公开了一种结构如(1)所示的3‑羰基5‑羟基酯类化合物的新型合成方法，所述方法包含以下步骤：以结构如式(2)所示的普通碳基类化合物与(3)多羰基二羧酸单边酯类化合物为原料，在有机溶剂A中，过渡金属催化剂的条件下直接充分反应，反应结束后反应体系经分离纯化，高收率高选择性得到所述的3‑羰基5‑羟基酯类化合物
• Candida Rugosa lipase-catalyzed kinetic resolution of β-hydroxy-β-arylpropionates and δ-hydroxy-δ-aryl-β-oxo-pentanoates
  作者：Chengfu Xu、Chengye Yuan

  DOI：10.1016/j.tet.2004.12.059

  日期：2005.2

  A simple and convenient method was reported for the preparation of optically active beta-hydroxy-beta-arylpropionates, delta-hydroxy-delta-aryl-beta-oxo-pentanoates and their butyryl derivatives via CRL-catalyzed hydrolysis. The optically active products are potential precursors of some chiral pharmaceuticals and natural products. (C) 2005 Elsevier Ltd. All rights reserved.
• 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.
• 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。