2-(1,4-dioxaspiro[4.5]dec-8-ylidenemethyl)-4-methoxy-1-naphthol | 1431376-56-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(1,4-dioxaspiro[4.5]dec-8-ylidenemethyl)-4-methoxy-1-naphthol
• 英文别名: 2-(1,4-Dioxaspiro[4.5]decan-8-ylidenemethyl)-4-methoxynaphthalen-1-ol；2-(1,4-dioxaspiro[4.5]decan-8-ylidenemethyl)-4-methoxynaphthalen-1-ol
• CAS: 1431376-56-5
• 化学式: C₂₀H₂₂O₄
• 分子量: 326.392
• InChiKey: OGVSVTNSOWDEHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-甲氧基-1-萘酚 、 8-[Chloro-(toluene-4-sulfinyl)-methylene]-1,4-dioxa-spiro[4.5]decane 在 正丁基锂 、 叔丁基氯化镁 、 异丙基氯化镁 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以62%的产率得到2-(1,4-dioxaspiro[4.5]dec-8-ylidenemethyl)-4-methoxy-1-naphthol
  参考文献：
  名称：

  Alkenylation of 1- and 2-Naphthols by Using Magnesium Alkylidene Carbenoids as Electrophilic Alkenylating Agents

  摘要：

  1- and 2-Naphthols were successfully alkenylated in a regioselective manner by treating the corresponding lithium 1- and 2-naphtholates with magnesium alkylidene carbenoids. The magnesium alkylidene carbenoids were generated in situ by a sulfoxide-magnesium exchange reaction of 1-chlorovinyl 4-tolyl sulfoxides with isopropylmagnesium chloride. The reaction of magnesium alkylidene carbenoids with lithium 2-naphtholates took place at the 1-position of the naphthyl ring to give 1-(alk-1-enyl)-2-naphthols in respectable yields. The alkenylation of 1-naphthols proceeded at the 2-position of the naphthol ring to give 2-(alk-1-enyl)-1-naphthols in yields of 56-67%. In contrast to the reaction of lithium naphtholates with magnesium alkylidene carbenoids, the reaction of lithium phenolates gave low yields of the corresponding alk-1-enyl aryl ethers.

  DOI：

  10.1055/s-0032-1318132

文献信息

• Alkenylation of 1- and 2-Naphthols by Using Magnesium Alkylidene Carbenoids as Electrophilic Alkenylating Agents
  作者：Tsuyoshi Satoh、Tsutomu Kimura、Masaya Watanabe、Gaku Kashiwamura、Jo Sakurada

  DOI：10.1055/s-0032-1318132

  日期：——

  1- and 2-Naphthols were successfully alkenylated in a regioselective manner by treating the corresponding lithium 1- and 2-naphtholates with magnesium alkylidene carbenoids. The magnesium alkylidene carbenoids were generated in situ by a sulfoxide-magnesium exchange reaction of 1-chlorovinyl 4-tolyl sulfoxides with isopropylmagnesium chloride. The reaction of magnesium alkylidene carbenoids with lithium 2-naphtholates took place at the 1-position of the naphthyl ring to give 1-(alk-1-enyl)-2-naphthols in respectable yields. The alkenylation of 1-naphthols proceeded at the 2-position of the naphthol ring to give 2-(alk-1-enyl)-1-naphthols in yields of 56-67%. In contrast to the reaction of lithium naphtholates with magnesium alkylidene carbenoids, the reaction of lithium phenolates gave low yields of the corresponding alk-1-enyl aryl ethers.