methyl (E)-2-(1-hydroxy-1-methylethyl)-5-phenyl-4-hexenoate | 604807-76-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: methyl (E)-2-(1-hydroxy-1-methylethyl)-5-phenyl-4-hexenoate
• 英文别名: methyl (E)-2-(2-hydroxypropan-2-yl)-5-phenylhex-4-enoate
• CAS: 604807-76-3
• 化学式: C₁₆H₂₂O₃
• 分子量: 262.349
• InChiKey: TXLYNAKHUIYMDB-ZRDIBKRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  methyl (E)-2-(1-hydroxy-1-methylethyl)-5-phenyl-4-hexenoate 在 VO[N-(2-hydroxyphenyl)salicylidenimine dianion](OEt) 叔丁基过氧化氢 、 吡啶溴化氢盐 作用下， 以 乙腈 为溶剂， 以43%的产率得到(5R,6S)-5-Bromo-2,2,6-trimethyl-6-phenyl-tetrahydro-pyran-3-carboxylic acid methyl ester
  参考文献：
  名称：

  A new synthesis of the 2,2,3,5,6,6-substituted tetrahydropyran aplysiapyranoid A and its 5-epimer

  摘要：

  The vanadium(V)-catalyzed oxidation of bromide in the presence of methyl (E)-2-(1-hydroxy-1-methylethyl)-5-phenyl-4-hexenoate furnished 5,6-trans-5-bromo-6-phenyl-2,2,6-trimethyl-3-methytoxycarbonyltetrahydropyran, which was converted into the marine natural product aplysiapyranoic A and its 5-epimer, via a short sequence of decarboxylative bromination and transition metal-based procedures for transforming a phenyl into a chlorovinyl Substituent. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01468-0
• 作为产物：
  描述：

  4-苯甲酰基丁酸甲酯 在 对甲苯磺酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 苯 为溶剂， 生成 methyl (E)-2-(1-hydroxy-1-methylethyl)-5-phenyl-4-hexenoate
  参考文献：
  名称：

  A new synthesis of the 2,2,3,5,6,6-substituted tetrahydropyran aplysiapyranoid A and its 5-epimer

  摘要：

  The vanadium(V)-catalyzed oxidation of bromide in the presence of methyl (E)-2-(1-hydroxy-1-methylethyl)-5-phenyl-4-hexenoate furnished 5,6-trans-5-bromo-6-phenyl-2,2,6-trimethyl-3-methytoxycarbonyltetrahydropyran, which was converted into the marine natural product aplysiapyranoic A and its 5-epimer, via a short sequence of decarboxylative bromination and transition metal-based procedures for transforming a phenyl into a chlorovinyl Substituent. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01468-0

文献信息

• A new synthesis of the 2,2,3,5,6,6-substituted tetrahydropyran aplysiapyranoid A and its 5-epimer
  作者：Jens Hartung、Marco Greb

  DOI：10.1016/s0040-4039(03)01468-0

  日期：2003.8

  The vanadium(V)-catalyzed oxidation of bromide in the presence of methyl (E)-2-(1-hydroxy-1-methylethyl)-5-phenyl-4-hexenoate furnished 5,6-trans-5-bromo-6-phenyl-2,2,6-trimethyl-3-methytoxycarbonyltetrahydropyran, which was converted into the marine natural product aplysiapyranoic A and its 5-epimer, via a short sequence of decarboxylative bromination and transition metal-based procedures for transforming a phenyl into a chlorovinyl Substituent. (C) 2003 Elsevier Ltd. All rights reserved.