methyl (E)-3-(2-bromo-3-cyclohex-2-en-1-yloxy-4-methoxyphenyl)prop-2-enoate | 157397-82-5

• 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 (E)-3-(2-bromo-3-cyclohex-2-en-1-yloxy-4-methoxyphenyl)prop-2-enoate
• CAS: 157397-82-5
• 化学式: C₁₇H₁₉BrO₄
• 分子量: 367.239
• InChiKey: MOIWFIQKSUVKHD-PKNBQFBNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (E)-3-(2-bromo-3-cyclohex-2-en-1-yloxy-4-methoxyphenyl)prop-2-enoate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以92%的产率得到(E)-3-(2-bromo-3-cyclohex-2-en-1-yloxy-4-methoxyphenyl)prop-2-enoic acid
  参考文献：
  名称：

  Stereochemistry of Radical Cyclizations to Side-Chain Olefinic Bonds. An Approach to Control of the C-9 Center of Morphine

  摘要：

  Styrenes of general structure 5 undergo tandem radical cyclization to cis,cis-hydrophenanthrofurans 9, products which contain the carbocyclic skeleton of the morphine alkaloids. Vinylurethane 5E-NHCO(2)Et cyclizes to 9 alpha via the intermediate radical 7E-NHCO(2)Et in the chair-chair conformation. Cyclization of 5Z-NHCO(2)Et also gives predominantly 9 alpha instead of the expected 9 beta. This anomaly is attributed to the isomerization of 5Z to 5E at a rate competitive with that of cyclization.

  DOI：

  10.1021/jo00093a026
• 作为产物：
  描述：

  2-溴-3-羟基-4-甲氧基苯甲醛 在 18-冠醚-6 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 methyl (E)-3-(2-bromo-3-cyclohex-2-en-1-yloxy-4-methoxyphenyl)prop-2-enoate
  参考文献：
  名称：

  Stereochemistry of Radical Cyclizations to Side-Chain Olefinic Bonds. An Approach to Control of the C-9 Center of Morphine

  摘要：

  Styrenes of general structure 5 undergo tandem radical cyclization to cis,cis-hydrophenanthrofurans 9, products which contain the carbocyclic skeleton of the morphine alkaloids. Vinylurethane 5E-NHCO(2)Et cyclizes to 9 alpha via the intermediate radical 7E-NHCO(2)Et in the chair-chair conformation. Cyclization of 5Z-NHCO(2)Et also gives predominantly 9 alpha instead of the expected 9 beta. This anomaly is attributed to the isomerization of 5Z to 5E at a rate competitive with that of cyclization.

  DOI：

  10.1021/jo00093a026

文献信息

• Stereochemistry of Radical Cyclizations to Side-Chain Olefinic Bonds. An Approach to Control of the C-9 Center of Morphine
  作者：Kathlyn A. Parker、Demosthenes Fokas

  DOI：10.1021/jo00093a026

  日期：1994.7

  Styrenes of general structure 5 undergo tandem radical cyclization to cis,cis-hydrophenanthrofurans 9, products which contain the carbocyclic skeleton of the morphine alkaloids. Vinylurethane 5E-NHCO(2)Et cyclizes to 9 alpha via the intermediate radical 7E-NHCO(2)Et in the chair-chair conformation. Cyclization of 5Z-NHCO(2)Et also gives predominantly 9 alpha instead of the expected 9 beta. This anomaly is attributed to the isomerization of 5Z to 5E at a rate competitive with that of cyclization.