ethyl (4S,5S,9E)-3-oxo-4,7,7,10-tetramethyl-4,5-methano-11-hydroxy-9-nonenoate | 199997-10-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl (4S,5S,9E)-3-oxo-4,7,7,10-tetramethyl-4,5-methano-11-hydroxy-9-nonenoate
• 英文别名: ethyl 3-[(1S,2S)-2-[(E)-6-hydroxy-2,2,5-trimethylhex-4-enyl]-1-methylcyclopropyl]-3-oxopropanoate
• CAS: 199997-10-9
• 化学式: C₁₈H₃₀O₄
• 分子量: 310.434
• InChiKey: LAPMQOUCRNTTAY-QAGQHWBLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (4S,5S,9E)-3-oxo-4,7,7,10-tetramethyl-4,5-methano-11-hydroxy-9-nonenoate 在 2,4,6-三甲基吡啶 、 氢氧化钾 、 caesium carbonate 、 甲基磺酰氯 、 lithium chloride 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.5h， 生成 (+)-Bicyclohumulenone
  参考文献：
  名称：

  Application of the chemo- and enantioselective cyclopropanation of polyenes to the total synthesis of (+)-bicyclohumulenone

  摘要：

  The chemo- and enantioselective cyclopropanation of a monoprotected bis(allylic alcohol) using a chiral dioxaborolane-derived ligand and Zn(CH2I)(2) was used as a key step in the total synthesis of (+)-bicyclohumulenone. The synthesis of this important perfume component was efficiently accomplished in 16 steps from diethyl 3,3-dimethylglutarate in 9% overall yield. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)01014-4
• 作为产物：
  描述：

  (2S,3S,7E)-2,5,5,8-tetramethyl-2,3-methano-9-(t-butyldiphenylsilyloxy)-7-nonen-1-al 在 N-甲基吲哚酮 、 四丙基高钌酸铵 、 4 A molecular sieve 、 四丁基氟化铵 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 6.75h， 生成 ethyl (4S,5S,9E)-3-oxo-4,7,7,10-tetramethyl-4,5-methano-11-hydroxy-9-nonenoate
  参考文献：
  名称：

  Application of the chemo- and enantioselective cyclopropanation of polyenes to the total synthesis of (+)-bicyclohumulenone

  摘要：

  The chemo- and enantioselective cyclopropanation of a monoprotected bis(allylic alcohol) using a chiral dioxaborolane-derived ligand and Zn(CH2I)(2) was used as a key step in the total synthesis of (+)-bicyclohumulenone. The synthesis of this important perfume component was efficiently accomplished in 16 steps from diethyl 3,3-dimethylglutarate in 9% overall yield. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)01014-4

文献信息

• Application of the chemo- and enantioselective cyclopropanation of polyenes to the total synthesis of (+)-bicyclohumulenone
  作者：AndréB. Charette、Hélène Juteau

  DOI：10.1016/s0040-4020(97)01014-4

  日期：1997.12

  The chemo- and enantioselective cyclopropanation of a monoprotected bis(allylic alcohol) using a chiral dioxaborolane-derived ligand and Zn(CH2I)(2) was used as a key step in the total synthesis of (+)-bicyclohumulenone. The synthesis of this important perfume component was efficiently accomplished in 16 steps from diethyl 3,3-dimethylglutarate in 9% overall yield. (C) 1997 Elsevier Science Ltd.