3-acetoxy-9c-(2′-cyanoethyl)-4a,5,6,7,9,9c-pentahydrophenanthro[4,5-bcd]furan | 1401226-30-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 3-acetoxy-9c-(2′-cyanoethyl)-4a,5,6,7,9,9c-pentahydrophenanthro[4,5-bcd]furan
• 英文别名: [(12S,13S)-13-(cyanomethyl)-15-oxatetracyclo[10.2.1.05,14.08,13]pentadeca-1,3,5(14),7-tetraen-2-yl] acetate
• CAS: 1401226-30-9
• 化学式: C₁₈H₁₇NO₃
• 分子量: 295.338
• InChiKey: AJSNDSLPRKWERU-MAUKXSAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  59.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-acetoxy-9c-(2′-cyanoethyl)-4a,5,6,7,9,9c-pentahydrophenanthro[4,5-bcd]furan 在 乙酰胺 、 palladium diacetate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 72.0h， 以93%的产率得到3-acetoxy-7a,9c-(amidoethano)-4a,5,6,7,9c-pentahydrophenanthro[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 4-二甲氨基吡啶 、 sodium periodate 、 四氧化锇 、 lithium aluminium tetrahydride 、 MMPP 、 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 、 叔丁醇 为溶剂， 反应 57.83h， 生成 3-acetoxy-9c-(2′-cyanoethyl)-4a,5,6,7,9,9c-pentahydrophenanthro[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