3-(1-ethoxyethenyl)-2-allyl-2-cyclohexen-1-one | 1401226-47-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(1-ethoxyethenyl)-2-allyl-2-cyclohexen-1-one
• 英文别名: 3-(1-Ethoxyethenyl)-2-prop-2-enylcyclohex-2-en-1-one；3-(1-ethoxyethenyl)-2-prop-2-enylcyclohex-2-en-1-one
• CAS: 1401226-47-8
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: PXFPUBIQCKJKRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(1-ethoxyethenyl)-2-allyl-2-cyclohexen-1-one 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以75%的产率得到3-(1-ethoxyethenyl)-2-allyl-2-cyclohexen-1-ol
  参考文献：
  名称：

  From Chiral ortho-Benzoquinone Monoketals to Nonracemic Indolinocodeines through Diels–Alder and Cope Reactions

  摘要：

  The S-dienol (-)-4 containing 10 carbons and one oxygen of the final product was prepared in 98.6% ee and 39% yield from cyclohexan-1,3-dione. It was attached to the aromatic ring as a monoether of catechol S-(-)-6 and subsequently subjected to oxidative ketalization in methanol. The allylated phenanthrofuran obtained was selectively oxidized at the terminal double bond. The fifth ring was completed by a "one-pot" amidation cyclization process promoted by palladium acetate. The final homochiral indolinocodeine (-)-31 was obtained in 16 steps and 3.6% overall yield from cyclohexan-1,3-dione.

  DOI：

  10.1021/jo3014098
• 作为产物：
  描述：

  2-烯丙基-1,3-环己二酮 在 叔丁基锂 、 potassium carbonate 作用下， 以 正己烷 、 丙酮 为溶剂， 反应 4.91h， 生成 3-(1-ethoxyethenyl)-2-allyl-2-cyclohexen-1-one
  参考文献：
  名称：

  From Chiral ortho-Benzoquinone Monoketals to Nonracemic Indolinocodeines through Diels–Alder and Cope Reactions

  摘要：

  The S-dienol (-)-4 containing 10 carbons and one oxygen of the final product was prepared in 98.6% ee and 39% yield from cyclohexan-1,3-dione. It was attached to the aromatic ring as a monoether of catechol S-(-)-6 and subsequently subjected to oxidative ketalization in methanol. The allylated phenanthrofuran obtained was selectively oxidized at the terminal double bond. The fifth ring was completed by a "one-pot" amidation cyclization process promoted by palladium acetate. The final homochiral indolinocodeine (-)-31 was obtained in 16 steps and 3.6% overall yield from cyclohexan-1,3-dione.

  DOI：

  10.1021/jo3014098

文献信息

• From Chiral <i>ortho</i>-Benzoquinone Monoketals to Nonracemic Indolinocodeines through Diels–Alder and Cope Reactions
  作者：Jihong Gao、Josephine Orso Simon、Russell Rodrigo、Abdeljalil Assoud

  DOI：10.1021/jo3014098

  日期：2013.1.4

  The S-dienol (-)-4 containing 10 carbons and one oxygen of the final product was prepared in 98.6% ee and 39% yield from cyclohexan-1,3-dione. It was attached to the aromatic ring as a monoether of catechol S-(-)-6 and subsequently subjected to oxidative ketalization in methanol. The allylated phenanthrofuran obtained was selectively oxidized at the terminal double bond. The fifth ring was completed by a "one-pot" amidation cyclization process promoted by palladium acetate. The final homochiral indolinocodeine (-)-31 was obtained in 16 steps and 3.6% overall yield from cyclohexan-1,3-dione.