(1R*,2S*,4S*)-1-methyl-4-(methylethyl)-1-(phenylmethoxy)-2-(2-propenyl)cyclohexane

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R*,2S*,4S*)-1-methyl-4-(methylethyl)-1-(phenylmethoxy)-2-(2-propenyl)cyclohexane
• 英文别名: [(1R,2S,4S)-1-methyl-4-propan-2-yl-2-prop-2-enylcyclohexyl]oxymethylbenzene
• 化学式: C₂₀H₃₀O
• 分子量: 286.458
• InChiKey: LRBXSLNIALYKAA-SLFFLAALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1R*,2S*,4S*)-1-methyl-4-(methylethyl)-1-(phenylmethoxy)-2-(2-propenyl)cyclohexane 在 臭氧 、 三苯基膦 作用下， 以 乙醚 为溶剂， 以83%的产率得到2-[(1R,2R,5S)-2-methyl-2-phenylmethoxy-5-propan-2-ylcyclohexyl]acetaldehyde
  参考文献：
  名称：

  Cyclohexenone Annelation by Alkylidene C−H Insertion:  Synthesis of Oxo-T-cadinol

  摘要：

  A new procedure for cyclohexenone annelation has been developed. Thus, alkylation of 4-isopropylcyclohexanone with allyl bromide gives, over several steps, ketone 8, Exposure to (trimethylsilyl)diazomethane and MeLi smoothly cyclized 8 to the cyclopentene 9 by insertion of the intermediate alkylidene carbene into the unactivated methylene CH. On debenzylation, ozonolysis, and subsequent aldol condensation, 9 is transformed into oxo-T-cadinol(1).

  DOI：

  10.1021/jo951949k
• 作为产物：
  描述：

  4-异丙基环己酮 在 copper(l) iodide 、 三乙基硼 、 四丁基碘化铵 、 双(三甲基硅烷基)氨基钾 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 、 甲苯 为溶剂， 反应 48.0h， 生成 (1R*,2S*,4S*)-1-methyl-4-(methylethyl)-1-(phenylmethoxy)-2-(2-propenyl)cyclohexane
  参考文献：
  名称：

  Cyclohexenone Annelation by Alkylidene C−H Insertion:  Synthesis of Oxo-T-cadinol

  摘要：

  A new procedure for cyclohexenone annelation has been developed. Thus, alkylation of 4-isopropylcyclohexanone with allyl bromide gives, over several steps, ketone 8, Exposure to (trimethylsilyl)diazomethane and MeLi smoothly cyclized 8 to the cyclopentene 9 by insertion of the intermediate alkylidene carbene into the unactivated methylene CH. On debenzylation, ozonolysis, and subsequent aldol condensation, 9 is transformed into oxo-T-cadinol(1).

  DOI：

  10.1021/jo951949k

文献信息

• Cyclohexenone Annelation by Alkylidene C−H Insertion:  Synthesis of Oxo-<i>T</i>-cadinol
  作者：Douglass F. Taber、Thomas E. Christos、C. Nicholas Hodge

  DOI：10.1021/jo951949k

  日期：1996.1.1

  A new procedure for cyclohexenone annelation has been developed. Thus, alkylation of 4-isopropylcyclohexanone with allyl bromide gives, over several steps, ketone 8, Exposure to (trimethylsilyl)diazomethane and MeLi smoothly cyclized 8 to the cyclopentene 9 by insertion of the intermediate alkylidene carbene into the unactivated methylene CH. On debenzylation, ozonolysis, and subsequent aldol condensation, 9 is transformed into oxo-T-cadinol(1).