5-hydroxycalamenene

• 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: 5-hydroxycalamenene
• 英文别名: (5S,8S)-2,5-dimethyl-8-propan-2-yl-5,6,7,8-tetrahydronaphthalen-1-ol
• 化学式: C₁₅H₂₂O
• 分子量: 218.339
• InChiKey: YXYMGKMWKSMRAB-JQWIXIFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-hydroxycalamenene 在 palladium on activated charcoal 作用下， 反应 5.0h， 生成 2,2,5,8-tetramethyl-2H-naphtho<1,8-bc>-furan
  参考文献：
  名称：

  Studies on Aromatic Sesquiterpenes. XII. Synthesis of (±)-cis-5-Hydroxycalamenene

  摘要：

  从邻甲酚出发，通过4-异丙基-5-甲氧基-6-甲基-1-四氢萘酮作为关键中间体，合成了(±)-顺-5-5-羟基卡拉梅烯，并通过光谱学手段与天然化合物进行了鉴定。

  DOI：

  10.1246/bcsj.63.272
• 作为产物：
  描述：

  1-hydroxy-8-isopropyl-5-methylnaphthalene-2-carbaldehyde 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 为溶剂， 以72%的产率得到5-hydroxycalamenene
  参考文献：
  名称：

  Total Synthesis of (±)- Cis -5-Hydroxycalamenene

  摘要：

  A total synthesis of (+/-)-cis-5-hydroxycalamenene 1 has been achieved from tetralone 5, which in turn was prepared from 5-methoxy-alpha-tetralone 3. Grignard reaction of compound 5 with isopropylmagnesium chloride, followed by dehydration and aromatization, provided the substituted naphthalene 7 whose conversion to (+/-)-cis-5-hydroxycalamenene 1 was accomplished by demethylation, formylation, and hydrogenation.

  DOI：

  10.1080/00397910802026204

文献信息

• Studies on Aromatic Sesquiterpenes. XII. Synthesis of (±)-<i>cis</i>-5-Hydroxycalamenene
  作者：Juichi Tanaka、Kazuo Adachi

  DOI：10.1246/bcsj.63.272

  日期：1990.1

  Starting from o-cresol, (±)-cis-5-5-hydroxycalamenene was synthesized through 4-isopropyl-5-methoxy-6-methyl-1-tetralone as a key intermediate and identified with the natural compound spectroscopically.

  从邻甲酚出发，通过4-异丙基-5-甲氧基-6-甲基-1-四氢萘酮作为关键中间体，合成了(±)-顺-5-5-羟基卡拉梅烯，并通过光谱学手段与天然化合物进行了鉴定。
• Total Synthesis of (±)-<b> <i>Cis</i> </b>-5-Hydroxycalamenene
  作者：Po S. Poon Ng、Ajoy K. Banerjee

  DOI：10.1080/00397910802026204

  日期：2008.6.20

  A total synthesis of (+/-)-cis-5-hydroxycalamenene 1 has been achieved from tetralone 5, which in turn was prepared from 5-methoxy-alpha-tetralone 3. Grignard reaction of compound 5 with isopropylmagnesium chloride, followed by dehydration and aromatization, provided the substituted naphthalene 7 whose conversion to (+/-)-cis-5-hydroxycalamenene 1 was accomplished by demethylation, formylation, and hydrogenation.