3-vinylcyclohex-2-en-1-yl methyl carbonate | 1401226-46-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: 3-vinylcyclohex-2-en-1-yl methyl carbonate
• 英文别名: (3-Ethenylcyclohex-2-en-1-yl) methyl carbonate；(3-ethenylcyclohex-2-en-1-yl) methyl carbonate
• CAS: 1401226-46-7
• 化学式: C₁₀H₁₄O₃
• 分子量: 182.219
• InChiKey: YVMBIBIQAPJOIK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-vinylcyclohex-2-en-1-yl methyl carbonate 、 邻苯二酚 在 palladium diacetate 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以50%的产率得到2-[(3-vinylcyclohex-2-en-1-yl)oxy]phenol
  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：

  二甲基二碳酸盐 、 alkaline earth salt of/the/ methylsulfuric acid 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以73%的产率得到3-vinylcyclohex-2-en-1-yl methyl carbonate
  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.