trans-1-(benzyloxy)-4,4-dimethyl-2-pentene | 146330-84-9

• 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: trans-1-(benzyloxy)-4,4-dimethyl-2-pentene
• 英文别名: [(E)-4,4-dimethylpent-2-enoxy]methylbenzene
• CAS: 146330-84-9
• 化学式: C₁₄H₂₀O
• 分子量: 204.312
• InChiKey: KWPIEVLTKLBPNY-JXMROGBWSA-N

物化性质

• 沸点：
  269.2±9.0 °C(predicted)
• 密度：
  0.923±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  5
• 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

• 作为反应物：
  描述：

  trans-1-(benzyloxy)-4,4-dimethyl-2-pentene 在 sodium azide 、 lithium perchlorate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 二乙二醇二甲醚 为溶剂， 反应 96.0h， 生成
  参考文献：
  名称：

  Regiochemical control of the ring opening of 1,2-epoxides by means of chelating processes. 5. Synthesis and reactions of some 2,3-epoxy-1-alkanol derivatives

  摘要：

  In order to study the effect of a remote polar functionality on the regiochemistry of the ring opening of aliphatic epoxides, the synthesis and some nucleophilic additions (methanolysis, azidolysis, and aminolysis) of suitable 2,3-epoxy-1-alkanol derivatives (epoxides trans-1a-d and cis-2) were carried out. The C-3 selectivity commonly observed when nonchelating ring opening conditions are used is lower than when the epoxides are allowed to react in the presence of metal ions (Li+, Mg2+, Zn2+) due to the probable intervention of bidentate-chelated intermediates in the latter case, and in some instances an almost complete C-3 regioselection is obtained. Under identical conditions involving chelation control, trans epoxide la shows higher C-3 selectivity than cis isomer 2. A free hydroxyl functionality is not necessary in order to observe chelation-controlled regioselectivity in the epoxides that we examined.

  DOI：

  10.1021/jo00057a040
• 作为产物：
  描述：

  ethyl (E)-4,4-dimethyl-2-pentenoate 在 sodium hydride 、 二异丁基氢化铝 作用下， 以 乙醚 、 正己烷 为溶剂， 反应 18.0h， 生成 trans-1-(benzyloxy)-4,4-dimethyl-2-pentene
  参考文献：
  名称：

  Regiochemical control of the ring opening of 1,2-epoxides by means of chelating processes. 5. Synthesis and reactions of some 2,3-epoxy-1-alkanol derivatives

  摘要：

  In order to study the effect of a remote polar functionality on the regiochemistry of the ring opening of aliphatic epoxides, the synthesis and some nucleophilic additions (methanolysis, azidolysis, and aminolysis) of suitable 2,3-epoxy-1-alkanol derivatives (epoxides trans-1a-d and cis-2) were carried out. The C-3 selectivity commonly observed when nonchelating ring opening conditions are used is lower than when the epoxides are allowed to react in the presence of metal ions (Li+, Mg2+, Zn2+) due to the probable intervention of bidentate-chelated intermediates in the latter case, and in some instances an almost complete C-3 regioselection is obtained. Under identical conditions involving chelation control, trans epoxide la shows higher C-3 selectivity than cis isomer 2. A free hydroxyl functionality is not necessary in order to observe chelation-controlled regioselectivity in the epoxides that we examined.

  DOI：

  10.1021/jo00057a040

文献信息

• Regiochemical control of the ring opening of 1,2-epoxides by means of chelating processes. 5. Synthesis and reactions of some 2,3-epoxy-1-alkanol derivatives
  作者：Marco Chini、Paolo Crotti、Lee A. Flippin、Cristina Gardelli、Elena Giovani、Franco Macchia、Mauro Pineschi

  DOI：10.1021/jo00057a040

  日期：1993.2

  In order to study the effect of a remote polar functionality on the regiochemistry of the ring opening of aliphatic epoxides, the synthesis and some nucleophilic additions (methanolysis, azidolysis, and aminolysis) of suitable 2,3-epoxy-1-alkanol derivatives (epoxides trans-1a-d and cis-2) were carried out. The C-3 selectivity commonly observed when nonchelating ring opening conditions are used is lower than when the epoxides are allowed to react in the presence of metal ions (Li+, Mg2+, Zn2+) due to the probable intervention of bidentate-chelated intermediates in the latter case, and in some instances an almost complete C-3 regioselection is obtained. Under identical conditions involving chelation control, trans epoxide la shows higher C-3 selectivity than cis isomer 2. A free hydroxyl functionality is not necessary in order to observe chelation-controlled regioselectivity in the epoxides that we examined.