trans-(RS,SR)-γ-hydroxy-β-methoxy-γ-phenylbutanoic acid lactone | 133101-74-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: trans-(RS,SR)-γ-hydroxy-β-methoxy-γ-phenylbutanoic acid lactone
• CAS: 133101-74-3；133101-75-4
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: AJPUAEGKRQWXOR-KOLCDFICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.69
• 重原子数：
  14.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2'-甲氧基苯乙酮 在 sodium hydroxide 、 双(三甲基硅烷基)氨基钾 、 二异丁基氢化铝 、 三氟乙酸 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 9.0h， 生成 trans-(RS,SR)-γ-hydroxy-β-methoxy-γ-phenylbutanoic acid lactone
  参考文献：
  名称：

  Stereoselective reduction of .gamma.-oxobutanoic acids using DIBAL-H and zinc chloride

  摘要：

  A variety of gamma-aromatic gamma-ketobutanoic acids can be reduced selectively, under optimized conditions, by the use of DIBAL-H and ZnCl2 to provide the (RS,SR)-gamma-aryl-gamma-hydroxy-beta-methylbutanoic acids. Further evidence has been gathered to support the hypothesis that the reaction proceeds by formation of a seven-membered ring complex with the aluminium or zinc atom bridging the ketone and carboxyl groups which preceeds the reduction step and that this templated reduction accounts for observed high diastereoselectivity. Also we have shown that some gamma-aryl-gamma-butyrolactones can be easily transformed via an oxidative cleavage of the aromatic ring to provide selective synthesis of either cis- or trans-tetrahydro-3-methyl-5-oxo-2-furancarboxylic acid derivatives.

  DOI：

  10.1021/jo00009a030

文献信息

• Regioselective Ring Opening and Isomerization Reactions of 3,4-Epoxyesters Catalyzed by Boron Trifluoride
  作者：Javier Izquierdo、Santiago Rodríguez、Florenci V. González

  DOI：10.1021/ol201378w

  日期：2011.8.5

  Efficient ring opening of 3,4-epoxyesters with alcohols to produce 4-alkoxy-3-hydroxyesters and their isomerization into 4-ketoesters using boron trifluoride as the catalyst are presented. Both transformations are simple and efficient methods for the synthesis of the above named synthetically useful compounds.

  提出了3，4-环氧酯与醇的有效开环以产生4-烷氧基-3-羟基酯，并使用三氟化硼作为催化剂将其异构化为4-酮酯。两种转化都是用于合成上述命名的有用化合物的简单而有效的方法。