3-methoxymethyl-2-phenyl-hex-5-ene

• 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-methoxymethyl-2-phenyl-hex-5-ene
• 英文别名: [(2R,3S)-3-(methoxymethyl)hex-5-en-2-yl]benzene
• 化学式: C₁₄H₂₀O
• 分子量: 204.312
• InChiKey: ADTDGOAUANNOPE-GXTWGEPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (E)-(3-methoxyprop-1-en-1-yl)benzene 、 2-丙烯基锂 、 碘甲烷 在 四甲基乙二胺 作用下， 生成 3-methoxymethyl-2-phenyl-hex-5-ene 、 3-methoxymethyl-2-phenyl-hex-5-ene
  参考文献：
  名称：

  Carbolithiation of cinnamyl methyl ethers and 2-cinnamyl-2-methyl-1,3-dioxolane: High diastereoselectivity after electrophilic substitution

  摘要：

  The carbolithiation of cinnamyl methyl ether 4 with tert-butyllithium, benzyllithium, and allyllithium is achieved in good yields. Consecutive treatment with electrophiles yields in all three cases a good diastereoselectivity thus confirming earlier results obtained in the reaction of secondary and tertiary cinnamyl amines. The ethylene acetal of 4-phenyl-3-buten-2-one 20 can also be carbolithiated with tert-butyllithium and the products exhibit even higher diastereomeric excesses.tert-Butyllithium has been added to alpha-methylcinnamyl methyl ether 17 showing complete diastereoselection in the nucleophilic addition step. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00018-6

文献信息

• Carbolithiation of cinnamyl methyl ethers and 2-cinnamyl-2-methyl-1,3-dioxolane: High diastereoselectivity after electrophilic substitution
  作者：Christian Mück-Lichtenfeld、Hubertus Ahlbrecht

  DOI：10.1016/s0040-4020(99)00018-6

  日期：1999.2

  The carbolithiation of cinnamyl methyl ether 4 with tert-butyllithium, benzyllithium, and allyllithium is achieved in good yields. Consecutive treatment with electrophiles yields in all three cases a good diastereoselectivity thus confirming earlier results obtained in the reaction of secondary and tertiary cinnamyl amines. The ethylene acetal of 4-phenyl-3-buten-2-one 20 can also be carbolithiated with tert-butyllithium and the products exhibit even higher diastereomeric excesses.tert-Butyllithium has been added to alpha-methylcinnamyl methyl ether 17 showing complete diastereoselection in the nucleophilic addition step. (C) 1999 Elsevier Science Ltd. All rights reserved.