(S)-2-[(2-allyl-3-vinylcyclohex-2-en-1-yl)oxy]phenol | 1401226-07-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (S)-2-[(2-allyl-3-vinylcyclohex-2-en-1-yl)oxy]phenol
• 英文别名: 2-[(1S)-3-ethenyl-2-prop-2-enylcyclohex-2-en-1-yl]oxyphenol
• CAS: 1401226-07-0
• 化学式: C₁₇H₂₀O₂
• 分子量: 256.345
• InChiKey: HXCZHHWHACAAER-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2-[(2-allyl-3-vinylcyclohex-2-en-1-yl)oxy]phenol 在 乙酰胺 、 4-二甲氨基吡啶 、 sodium periodate 、 四氧化锇 、 MMPP 、 palladium diacetate 、 sodium hydride 、 potassium carbonate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 丙酮 、 mineral oil 、 叔丁醇 为溶剂， 反应 108.16h， 生成 3-methoxy-7a,9c-(methylamidoethano)-4a,5,6,7,9cpentahydrophenanthro[4,5-bcd]furan
  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：

  1,3-环己二酮 在 lithium aluminium tetrahydride 、 二苯基二硒醚 、 双氧水 、 铜 、 potassium carbonate 、 N,N-二甲基乙二胺 、 potassium hydroxide 、 儿萘酚硼烷 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 丙酮 、 甲苯 为溶剂， 反应 40.67h， 生成 (S)-2-[(2-allyl-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

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.