(+/-)-(3-(benzyloxymethoxy)hex-5-enyl)benzene | 916426-89-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+/-)-(3-(benzyloxymethoxy)hex-5-enyl)benzene
• 英文别名: 1-Phenylhex-5-en-3-yloxymethoxymethylbenzene；1-phenylhex-5-en-3-yloxymethoxymethylbenzene
• CAS: 916426-89-6
• 化学式: C₂₀H₂₄O₂
• 分子量: 296.409
• InChiKey: DYDOOLDSMSYKLL-UHFFFAOYSA-N

物化性质

• 沸点：
  413.4±45.0 °C(Predicted)
• 密度：
  1.021±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-(3-(benzyloxymethoxy)hex-5-enyl)benzene 在 一氯化碘 、 锂硼氢 作用下， 以 二氯甲烷 、 甲苯 、 四氢呋喃 为溶剂， 反应 0.34h， 以67%的产率得到((3RS,5RS)-5-benzyloxy-6-iodo-3-methoxyhexyl)benzene
  参考文献：
  名称：

  Electrophile-Induced Ether Transfer:  A New Approach to Polyketide Structural Units

  摘要：

  [GRAPHICS]A strategically novel approach to the formation of syn-1,3-diol mono- and diethers through electrophilic activation of homoallylic alkoxymethyl ethers has been developed. The resulting polyketide-like synthetic fragments are generated in good yield and with excellent stereocontrol. A chairlike transition state is proposed to account for the high stereoselectivity. Varying the conditions of the reaction workup results in the efficient generation of mono- and diether containing structural units common to polyketide natural products.

  DOI：

  10.1021/ol0623318
• 作为产物：
  描述：

  苄基氯甲基醚 、 1-苯基-5-己烯-3-醇 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以4.03 g的产率得到(+/-)-(3-(benzyloxymethoxy)hex-5-enyl)benzene
  参考文献：
  名称：

  Electrophile-Induced Ether Transfer:  A New Approach to Polyketide Structural Units

  摘要：

  [GRAPHICS]A strategically novel approach to the formation of syn-1,3-diol mono- and diethers through electrophilic activation of homoallylic alkoxymethyl ethers has been developed. The resulting polyketide-like synthetic fragments are generated in good yield and with excellent stereocontrol. A chairlike transition state is proposed to account for the high stereoselectivity. Varying the conditions of the reaction workup results in the efficient generation of mono- and diether containing structural units common to polyketide natural products.

  DOI：

  10.1021/ol0623318

文献信息

• Electrophile-Induced Ether Transfer:  A New Approach to Polyketide Structural Units
  作者：Kai Liu、Richard E. Taylor、Rendy Kartika

  DOI：10.1021/ol0623318

  日期：2006.11.9

  [GRAPHICS]A strategically novel approach to the formation of syn-1,3-diol mono- and diethers through electrophilic activation of homoallylic alkoxymethyl ethers has been developed. The resulting polyketide-like synthetic fragments are generated in good yield and with excellent stereocontrol. A chairlike transition state is proposed to account for the high stereoselectivity. Varying the conditions of the reaction workup results in the efficient generation of mono- and diether containing structural units common to polyketide natural products.