5-hydroxy-5-phenyl-pent-2-enoic acid methyl ester | 1004960-84-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 5-hydroxy-5-phenyl-pent-2-enoic acid methyl ester
• 英文别名: (R)-(E)-methyl 5-hydroxy-5-phenylpent-2-enoate；(E)-methyl (5R)-hydroxy-5-phenylpent-2-enoate；methyl (E,5R)-5-hydroxy-5-phenylpent-2-enoate
• CAS: 1004960-84-2
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: VXFYGMBFRDCANQ-FZPLPXEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-hydroxy-5-phenyl-pent-2-enoic acid methyl ester 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 (R)-6-phenyl-5,6-dihydro-2H-pyran-2-one
  参考文献：
  名称：

  Enzyme mediated kinetic resolution of δ-hydroxy-α,β-unsaturated esters as a route to optically active δ-lactones

  摘要：

  A novel synthetic route to optically active saturated and unsaturated delta-lactones based on enzymatic kinetic resolution and ring-closing metathesis reactions has been proposed. The influence of temperature, co-solvent, organic additives and the substrate structure on the catalytic behavior of selected hydrolases was studied. The substantial impact of the organic co-solvent and surfactant type on the enzymatic activity and enantioselectivity was observed providing enantiomerically pure delta-hydroxy-alpha,beta-unsaturated esters. The established protocol combining enzymatic kinetic resolution with ring closing metathesis was successfully applied in the synthesis of the enantiomerically pure (6R)-phenyl-5,6-dihydro-2H-pyran-2-one which plays crucial role in the synthesis of the number of bioactive compounds. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2017.05.003
• 作为产物：
  描述：

  methyl 5-hydroxy-5-phenyl-2-pentenoate 在 4-二甲氨基吡啶 、 Pseudomonas fluorescence lipase 、 水 、 三乙胺 作用下， 以 aq. phosphate buffer 、 二氯甲烷 、 甲基叔丁基醚 为溶剂， 反应 25.33h， 生成 5-hydroxy-5-phenyl-pent-2-enoic acid methyl ester
  参考文献：
  名称：

  Enzyme mediated kinetic resolution of δ-hydroxy-α,β-unsaturated esters as a route to optically active δ-lactones

  摘要：

  A novel synthetic route to optically active saturated and unsaturated delta-lactones based on enzymatic kinetic resolution and ring-closing metathesis reactions has been proposed. The influence of temperature, co-solvent, organic additives and the substrate structure on the catalytic behavior of selected hydrolases was studied. The substantial impact of the organic co-solvent and surfactant type on the enzymatic activity and enantioselectivity was observed providing enantiomerically pure delta-hydroxy-alpha,beta-unsaturated esters. The established protocol combining enzymatic kinetic resolution with ring closing metathesis was successfully applied in the synthesis of the enantiomerically pure (6R)-phenyl-5,6-dihydro-2H-pyran-2-one which plays crucial role in the synthesis of the number of bioactive compounds. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2017.05.003

文献信息

• Oxazaborolidinone-Promoted Vinylogous Mukaiyama Aldol Reactions
  作者：Serkan Simsek、Melanie Horzella、Markus Kalesse

  DOI：10.1021/ol702640w

  日期：2007.12.1

  delta-Hydroxy-alpha,beta-unsaturated carbonyl compounds were prepared in one step via the vinylogous Mukaiyama aldol reactions with O,O-silyl ketene acetals. Isopropyl alcohol as additive and tryptophane-based B-phenyloxazaborolidinone were required for obtaining the gamma-alkylated product in high enantioselectivities.

  通过乙烯基的Mukaiyama醇醛醇缩醛与O，O-甲硅烷基乙烯酮缩醛的一步制备δ-羟基-α，β-不饱和羰基化合物。为了获得高对映选择性，需要使用异丙醇作为添加剂和色氨酸基B-苯基氧杂氮杂硼烷酮。