(3-Hydroxy-2-methylidene-5-phenylpentyl) acetate | 235090-81-0

• 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: (3-Hydroxy-2-methylidene-5-phenylpentyl) acetate
• 英文别名: (3-hydroxy-2-methylidene-5-phenylpentyl) acetate
• CAS: 235090-81-0
• 化学式: C₁₄H₁₈O₃
• 分子量: 234.295
• InChiKey: KMRUULKWTVXGPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 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：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3-Hydroxy-2-methylidene-5-phenylpentyl) acetate 在 咪唑 、 Grubbs catalyst first generation 、 草酰氯 、 双(三甲基硅烷基)氨基钾 、 potassium carbonate 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氘代苯 为溶剂， -78.0~30.0 ℃ 、689.47 kPa 条件下， 反应 6.0h， 生成 (tert-butyl)(dimethyl)(2-methylidene-1-phenethyl-but-3-enyloxy)silane
  参考文献：
  名称：

  Equilibrium Control in Enyne Metathesis:  Crossover Studies and the Kinetic Reactivity of (E,Z)-1,3-Disubstituted-1,3-Dienes

  摘要：

  The stereoselectivity of diene bond formation in the ruthenium-carbene mediated intermolecular enyne metathesis was studied. Initial reaction between an alkyne and 1-hexene gave mixtures of E- and Z-isomers in the newly formed 1,3-diene. However, over time the mixtures equilibrated to form mostly the diene of the E-configuration. To evaluate individual reactivity of the E- and Z-dienes, they were independently synthesized. The E-diene was found to be kinetically-stable under nominal metathesis conditions while the Z-diene isomerized to the E-isomer. The Z-isomeric dienes were found to react with other alkenes to produce a new diene of E-configuration. A secondary metathesis mechanism involving ruthenium alkylidene intermediates was invoked to explain the dynamic stereochemistry observed in this study.

  DOI：

  10.1021/jo0482209
• 作为产物：
  描述：

  苯丙醛 、 2-溴-2-丙烯基乙酸酯 在 chromium dichloride 、 nickel dichloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以93%的产率得到(3-Hydroxy-2-methylidene-5-phenylpentyl) acetate
  参考文献：
  名称：

  2-Bromoallyl Acetate:  A Useful Structural Unit for Sequential Carbon−Carbon Bond Formation

  摘要：

  [GRAPHICS]2-Bromoallyl acetate has been shown to be an efficient substrate for Ni(II)/Cr(II) mediated coupling reactions with a variety of aliphatic and aryl aldehydes, Surprisingly, elimination of acetate from the intermediate vinylchromium species does not appear to compete with carbon-carbon bond formation. In addition, the allylic acetate products have been shown to be useful allyl nucleophile precursors through palladium mediated reactions. These results suggest that acyloxyalkenyl bromides are efficient linchpins for multiple carbon-carbon bond formation.

  DOI：

  10.1021/ol9900865

文献信息

• Equilibrium Control in Enyne Metathesis:  Crossover Studies and the Kinetic Reactivity of (<i>E,Z</i>)-1,3-Disubstituted-1,3-Dienes
  作者：Anthony J. Giessert、Steven T. Diver

  DOI：10.1021/jo0482209

  日期：2005.2.1

  The stereoselectivity of diene bond formation in the ruthenium-carbene mediated intermolecular enyne metathesis was studied. Initial reaction between an alkyne and 1-hexene gave mixtures of E- and Z-isomers in the newly formed 1,3-diene. However, over time the mixtures equilibrated to form mostly the diene of the E-configuration. To evaluate individual reactivity of the E- and Z-dienes, they were independently synthesized. The E-diene was found to be kinetically-stable under nominal metathesis conditions while the Z-diene isomerized to the E-isomer. The Z-isomeric dienes were found to react with other alkenes to produce a new diene of E-configuration. A secondary metathesis mechanism involving ruthenium alkylidene intermediates was invoked to explain the dynamic stereochemistry observed in this study.
• 2-Bromoallyl Acetate:  A Useful Structural Unit for Sequential Carbon−Carbon Bond Formation
  作者：Richard E. Taylor、Jeffrey P. Ciavarri

  DOI：10.1021/ol9900865

  日期：1999.8.1

  [GRAPHICS]2-Bromoallyl acetate has been shown to be an efficient substrate for Ni(II)/Cr(II) mediated coupling reactions with a variety of aliphatic and aryl aldehydes, Surprisingly, elimination of acetate from the intermediate vinylchromium species does not appear to compete with carbon-carbon bond formation. In addition, the allylic acetate products have been shown to be useful allyl nucleophile precursors through palladium mediated reactions. These results suggest that acyloxyalkenyl bromides are efficient linchpins for multiple carbon-carbon bond formation.