3-Methyl-4-oxo-6-phenyl-5-hexensaeure-methylester | 131407-57-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 3-Methyl-4-oxo-6-phenyl-5-hexensaeure-methylester
• 英文别名: methyl (E)-3-methyl-4-oxo-6-phenylhex-5-enoate
• CAS: 131407-57-3
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: CYTVHCZVMWZOJM-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Methyl-4-oxo-6-phenyl-5-hexensaeure-methylester 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 生成 (E)-3-methyl-4-oxo-6-phenyl-5-hexenoic acid
  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
• 作为产物：
  描述：

  4-methoxy-2-methyl-4-oxobutanoic acid 在 palladium diacetate 、 四(三苯基膦)钯 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 、 三苯基膦 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 为溶剂， 反应 20.0h， 生成 3-Methyl-4-oxo-6-phenyl-5-hexensaeure-methylester
  参考文献：
  名称：

  Concise total synthesis of 9-methoxystrobilurin A

  摘要：

  Total synthesis of a potent antifungal and cytostatic 9-methoxystrobilurin A was achieved by developing a concise and general route to beta-methoxy acrylate. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00559-1

文献信息

• Wienand, Anette; Reissig, Hans-Ulrich, Chemische Berichte, 1991, vol. 124, # 4, p. 957 - 965
  作者：Wienand, Anette、Reissig, Hans-Ulrich

  DOI：——

  日期：——
• WIENAND, ANETTE;REISS. IG, HANS-ULRICH, CHEM. BER., 124,(1991) N, C. 957-965
  作者：WIENAND, ANETTE、REISS. IG, HANS-ULRICH

  DOI：——

  日期：——
• Stereoselective reduction of .gamma.-oxobutanoic acids using DIBAL-H and zinc chloride
  作者：R. Frenette、M. Monette、M. A. Bernstein、R. N. Young、T. R. Verhoeven

  DOI：10.1021/jo00009a030

  日期：1991.4

  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.
• Concise total synthesis of 9-methoxystrobilurin A
  作者：Hiromi Uchiro、Koh Nagasawa、Yasuyuki Aiba、Susumu Kobayashi

  DOI：10.1016/s0040-4039(00)00559-1

  日期：2000.5

  Total synthesis of a potent antifungal and cytostatic 9-methoxystrobilurin A was achieved by developing a concise and general route to beta-methoxy acrylate. (C) 2000 Elsevier Science Ltd. All rights reserved.