ethyl 5-hydroxy-5-(4-methoxyphenyl)-3-oxopentanoate | 682770-51-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ethyl 5-hydroxy-5-(4-methoxyphenyl)-3-oxopentanoate
• CAS: 682770-51-0
• 化学式: C₁₄H₁₈O₅
• 分子量: 266.294
• InChiKey: KJSOXLDEIVMSCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.64
• 重原子数：
  19.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  72.83
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl 5-hydroxy-5-(4-methoxyphenyl)-3-oxopentanoate 在 4-二甲氨基吡啶 、 ammonium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 5-(4-甲氧基苯基)-3-氧代-4-戊烯酸乙酯
  参考文献：
  名称：

  Candida Rugosa lipase-catalyzed kinetic resolution of β-hydroxy-β-arylpropionates and δ-hydroxy-δ-aryl-β-oxo-pentanoates

  摘要：

  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.

  DOI：

  10.1016/j.tet.2004.12.059
• 作为产物：
  描述：

  ethyl 5-(2-chloroacetyl)oxy-5-(4-methoxyphenyl)-3-oxopentanoate 在 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 5-(4-甲氧基苯基)-3-氧代-4-戊烯酸乙酯 、 ethyl 5-hydroxy-5-(4-methoxyphenyl)-3-oxopentanoate
  参考文献：
  名称：

  Candida Rugosa lipase-catalyzed kinetic resolution of β-hydroxy-β-arylpropionates and δ-hydroxy-δ-aryl-β-oxo-pentanoates

  摘要：

  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.

  DOI：

  10.1016/j.tet.2004.12.059

文献信息

• 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。
• Construction of Two Vicinal Quaternary Carbons by Asymmetric Allylic Alkylation: Total Synthesis of Hyperolactone C and (−)-Biyouyanagin A
  作者：Chao Du、Liqi Li、Ying Li、Zhixiang Xie

  DOI：10.1002/anie.200902908

  日期：2009.10.5

  Call on triple A: Palladium‐catalyzed asymmetric allylic alkylation (Pd‐AAA; see scheme) has enabled a concise and efficient synthesis of hyperolactone C and (−)‐biyouyanagin A in only six (20 % overall yield) and seven (8 % overall yield) steps, respectively. The enantiomers of these natural products were also prepared by exploiting the same methodology.

  呼吁三A：钯催化的不对称烯丙基烷基化（Pd-AAA;参见方案）使得高内酯C和（-）-双油烟精A的简明而高效的合成仅六种（总收率20％）和七种（8％）总产量）步骤。这些天然产物的对映异构体也采用相同的方法制备。
• ——
  作者：I. P. Lokot'、F. S. Pashkovskii、F. A. Lakhvich

  DOI：10.1023/a:1011913328785

  日期：——
• 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.