(E)-3-(2-bromo-3-cyclohex-2-en-1-yloxy-4-methoxyphenyl)prop-2-enenitrile | 157397-86-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-3-(2-bromo-3-cyclohex-2-en-1-yloxy-4-methoxyphenyl)prop-2-enenitrile
• CAS: 157397-86-9
• 化学式: C₁₆H₁₆BrNO₂
• 分子量: 334.213
• InChiKey: MWWIWEBTQZVHEJ-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  42.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-3-(2-bromo-3-cyclohex-2-en-1-yloxy-4-methoxyphenyl)prop-2-enenitrile 在 偶氮二异丁腈 、 三(三甲基硅基)硅烷 作用下， 以 苯 为溶剂， 以44%的产率得到(4aR,7aR,8R,9cR)-3-Methoxy-4a,5,6,7,7a,8,9,9c-octahydro-phenanthro[4,5-bcd]furan-8-carbonitrile
  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 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 (E)-3-(2-bromo-3-cyclohex-2-en-1-yloxy-4-methoxyphenyl)prop-2-enenitrile
  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.