methyl 3-(4-acetoxy-3-methoxy-5-methylphenyl)-2-(bromomethyl)propenoate | 496024-89-6

• 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: methyl 3-(4-acetoxy-3-methoxy-5-methylphenyl)-2-(bromomethyl)propenoate
• 英文别名: methyl (Z)-3-(4-acetyloxy-3-methoxy-5-methylphenyl)-2-(bromomethyl)prop-2-enoate
• CAS: 496024-89-6
• 化学式: C₁₅H₁₇BrO₅
• 分子量: 357.201
• InChiKey: RPAOUPCEIOQQNN-WUXMJOGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3-(4-acetoxy-3-methoxy-5-methylphenyl)-2-(bromomethyl)propenoate 在 sodium tetrahydroborate 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.83h， 生成 1-[2-carbomethoxy-3-(4-acetoxy-3-methoxy-5-methylphenyl)-2-propenyl]-(4S)-acetoxy-(5R)-hydroxypyrrolidin-2-one
  参考文献：
  名称：

  An Asymmetric Synthesis of Aza Analogues of the Tricyclic Skeleton of Daphnane and the ABC Ring System of Phorbol

  摘要：

  An asymmetric synthesis of aza analogues of the ABC ring system of phorbol and related compounds containing the 5-7-6-fused framework of daphnane involved construction of the central seven-membered ring by a regioselective reduction of a chiral imide and cyclization with trifluoromethanesulfonic acid. Subsequent demethylation and oxidative dearomatization of ring C afforded an enantiopure dienone 20 with the same relative and absolute configuration at the 9- and 10-positions of the phorbol skeleton.

  DOI：

  10.1021/jo0205816
• 作为产物：
  描述：

  4-hydroxy-3-methoxy-5-methylbenzaldehyde 在 sodium hydroxide 、 氢溴酸 、 四丁基硫酸氢铵 、 奎宁环-3-醇 作用下， 以 二氯甲烷 为溶剂， 反应 115.0h， 生成 methyl 3-(4-acetoxy-3-methoxy-5-methylphenyl)-2-(bromomethyl)propenoate
  参考文献：
  名称：

  An Asymmetric Synthesis of Aza Analogues of the Tricyclic Skeleton of Daphnane and the ABC Ring System of Phorbol

  摘要：

  An asymmetric synthesis of aza analogues of the ABC ring system of phorbol and related compounds containing the 5-7-6-fused framework of daphnane involved construction of the central seven-membered ring by a regioselective reduction of a chiral imide and cyclization with trifluoromethanesulfonic acid. Subsequent demethylation and oxidative dearomatization of ring C afforded an enantiopure dienone 20 with the same relative and absolute configuration at the 9- and 10-positions of the phorbol skeleton.

  DOI：

  10.1021/jo0205816

文献信息

• An Asymmetric Synthesis of Aza Analogues of the Tricyclic Skeleton of Daphnane and the ABC Ring System of Phorbol
  作者：Charles M. Marson、Jennifer H. Pink、David Hall、Michael B. Hursthouse、Abdul Malik、Christopher Smith

  DOI：10.1021/jo0205816

  日期：2003.2.1

  An asymmetric synthesis of aza analogues of the ABC ring system of phorbol and related compounds containing the 5-7-6-fused framework of daphnane involved construction of the central seven-membered ring by a regioselective reduction of a chiral imide and cyclization with trifluoromethanesulfonic acid. Subsequent demethylation and oxidative dearomatization of ring C afforded an enantiopure dienone 20 with the same relative and absolute configuration at the 9- and 10-positions of the phorbol skeleton.