3-(3'-acetoxybutyl)-5-t-butyldimethylsilyloxy-2,4,4-trimethylcyclohex-2-enone | 302329-62-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(3'-acetoxybutyl)-5-t-butyldimethylsilyloxy-2,4,4-trimethylcyclohex-2-enone
• 英文别名: 4-[5-[Tert-butyl(dimethyl)silyl]oxy-2,6,6-trimethyl-3-oxocyclohexen-1-yl]butan-2-yl acetate
• CAS: 302329-62-0
• 化学式: C₂₁H₃₈O₄Si
• 分子量: 382.616
• InChiKey: ZIEWNOHIAFBVJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.42
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(3'-acetoxybutyl)-5-t-butyldimethylsilyloxy-2,4,4-trimethylcyclohex-2-enone 在 jones reagent 、 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 1.5h， 生成 5-t-butyldimethylsilyloxy-3-(3'-oxobutyl)-2,4,4-trimethylcyclohex-2-enone
  参考文献：
  名称：

  Synthesis of Natural Oxygenated Monocarbocyclic Sesquiterpenoids from 6,7-Epoxygeranyl Acetate

  摘要：

  Natural sesquiterpenes 5-(2/,5'-epoxy-2',6',6'-trimethyl)cyclohexyl-3-methyl-1-penten-3-ol (5), cis-3-[(E)-5'-hydroxy-3'-methyl-3'-pentenyl]-2,2-dimethyl-4-methylenecyclohexanol (elegansidiol) (6), 4-(5'-acetoxy-2',6',6'-trimethyl)cyclohex-2'-enyl-3-methyl-1-penten-3-ol (7) and 5-acetoxy-3-(3-hydroxy-3-methylpent-4-enyl)2,4,4-trimethylcyclohex-2-enone (8) were prepared from 6,7-epoxygeranyl acetate (9), via (2',5'-epoxy-2',6',6'-trimethyl)cyclohexylmethyl tosylate (10), for the first time. 5 is an intermediate in the synthesis of the sesquiterpene-coumarin ether (+/-)-farnesiferol C (1). The preparation of suitable intermediates for synthesising related natural farmesiferol B (3) and D (4) is also reported. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00560-3
• 作为产物：
  描述：

  4-(2',5'-epoxy-2',6',6'-trimethyl)cyclohexyl-2-butanol 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 sodium chromate(VI) 、 sodium acetate 、 三溴化硼 作用下， 以 二氯甲烷 、 乙酸酐 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 53.25h， 生成 3-(3'-acetoxybutyl)-5-t-butyldimethylsilyloxy-2,4,4-trimethylcyclohex-2-enone
  参考文献：
  名称：

  Synthesis of Natural Oxygenated Monocarbocyclic Sesquiterpenoids from 6,7-Epoxygeranyl Acetate

  摘要：

  Natural sesquiterpenes 5-(2/,5'-epoxy-2',6',6'-trimethyl)cyclohexyl-3-methyl-1-penten-3-ol (5), cis-3-[(E)-5'-hydroxy-3'-methyl-3'-pentenyl]-2,2-dimethyl-4-methylenecyclohexanol (elegansidiol) (6), 4-(5'-acetoxy-2',6',6'-trimethyl)cyclohex-2'-enyl-3-methyl-1-penten-3-ol (7) and 5-acetoxy-3-(3-hydroxy-3-methylpent-4-enyl)2,4,4-trimethylcyclohex-2-enone (8) were prepared from 6,7-epoxygeranyl acetate (9), via (2',5'-epoxy-2',6',6'-trimethyl)cyclohexylmethyl tosylate (10), for the first time. 5 is an intermediate in the synthesis of the sesquiterpene-coumarin ether (+/-)-farnesiferol C (1). The preparation of suitable intermediates for synthesising related natural farmesiferol B (3) and D (4) is also reported. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00560-3