methyl [(E)-1-phenylhex-4-en-3-yl] carbonate | 1370526-49-0

• 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: methyl [(E)-1-phenylhex-4-en-3-yl] carbonate
• CAS: 1370526-49-0
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: PLIYAAXUPUKYOY-XVNBXDOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl [(E)-1-phenylhex-4-en-3-yl] carbonate 、 联硼酸频那醇酯 在 potassium tert-butylate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 copper(l) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以95%的产率得到(E)-4,4,5,5-tetramethyl-2-(6-phenylhex-3-en-2-yl)-1,3,2-dioxaborolane
  参考文献：
  名称：

  Practical procedure for copper(I)-catalyzed allylic boryl substitution with stoichiometric alkoxide base

  摘要：

  We have developed a useful procedure for borylation using catalytic CuCl/Xantphos and stoichiometric K(O-t-Bu): the highly versatile method is suitable for the synthesis of allylboronates including those with terminal and internal allylic systems, cyclic structures, and functional groups. Optically active allylboronates were synthesized from prochiral substrates with a chiral diphosphine ligand using this procedure. The reaction rate is generally higher than the original Cu(O-t-Bu)/ligand catalyst system, which we previously reported. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.08.081

文献信息

• Copper(I)-Catalyzed Allylic Substitution of Silyl Nucleophiles through SiSi Bond Activation
  作者：Hajime Ito、Yuko Horita、Masaya Sawamura

  DOI：10.1002/adsc.201100819

  日期：2012.3.16

  We report the first copper(I)‐catalyzed reaction between a disilane and allylic carbonates to produce allylsilanes. The silyl nucleophilic substitution proceeded primarily in a SN2 fashion whereas SN2′ products were also obtained through σ‐π‐σ isomerization of the copper(III) intermediate depending on the substrate’s steric bulk.

  我们报告了乙硅烷与烯丙基碳酸酯之间的第一个铜（I）催化反应，生成烯丙基硅烷。甲硅烷基亲核取代主要以S N 2方式进行，而S N 2'产物也通过铜（III）中间体的σ-π-σ异构化而获得，具体取决于底物的空间体积。
• Practical procedure for copper(I)-catalyzed allylic boryl substitution with stoichiometric alkoxide base
  作者：Hajime Ito、Takanori Miya、Masaya Sawamura

  DOI：10.1016/j.tet.2011.08.081

  日期：2012.4

  We have developed a useful procedure for borylation using catalytic CuCl/Xantphos and stoichiometric K(O-t-Bu): the highly versatile method is suitable for the synthesis of allylboronates including those with terminal and internal allylic systems, cyclic structures, and functional groups. Optically active allylboronates were synthesized from prochiral substrates with a chiral diphosphine ligand using this procedure. The reaction rate is generally higher than the original Cu(O-t-Bu)/ligand catalyst system, which we previously reported. (C) 2011 Elsevier Ltd. All rights reserved.