Methyl syn-(Z)-2-(1-hydroxy-1-benzyl)-3-pentenoate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: Methyl syn-(Z)-2-(1-hydroxy-1-benzyl)-3-pentenoate
• 英文别名: methyl (Z,2S)-2-[(S)-hydroxy(phenyl)methyl]pent-3-enoate
• 化学式: C₁₃H₁₆O₃
• 分子量: 220.268
• InChiKey: MXAHTGJUQPFFAG-MOKYYMMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 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 syn-(Z)-2-(1-hydroxy-1-benzyl)-3-pentenoate 在 碘 、 碳酸氢钠 作用下， 以 乙腈 为溶剂， 生成 (2RS,3RS,4SR,5SR)-2-Phenyl-3-carbmethoxy-4-iodo-5-methyltetrahydrofuran 、 (2RS,3RS,4RS,5RS)-2-Phenyl-3-carbmethoxy-4-iodo-5-methyltetrahydrofuran
  参考文献：
  名称：

  Tandem Aldol-Cyclization Sequence for the Construction of Cyclic Ethers. The Formation of Substituted Tetrahydrofurans

  摘要：

  The application of a tandem deconjugative aldol-cyclization Sequence for the construction of substituted tetrahydrofurans was examined. The aldol condensation of alkenoates proceeded with alkylation at the alpha-position to generate homoallylic alcohol moieties. These compounds could be induced to cyclize under the influence of iodine via an endo mode. The stereoselectivity for the cyclization occurred in good to excellent fashion. X-ray crystal structure analysis of three of the tetrahydrofurans established unambiguously the product stereochemistry. This was: used to propose a transition structure for the cyclization which correctly predicts the observed product stereochemistry. By this method, virtually all the possible stereoisomers for the substituted tetrahydrofurans can be constructed by judicious choice of aldol product and/or olefin geometry.

  DOI：

  10.1021/jo00101a024
• 作为产物：
  描述：

  反-2-戊酸甲酯 、 苯甲醛 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 正己烷 为溶剂， 生成 Methyl syn-(Z)-2-(1-hydroxy-1-benzyl)-3-pentenoate 、 Methyl anti-(Z)-2-(1-hydroxy-1-benzyl)-3-pentenoate
  参考文献：
  名称：

  Tandem Aldol-Cyclization Sequence for the Construction of Cyclic Ethers. The Formation of Substituted Tetrahydrofurans

  摘要：

  The application of a tandem deconjugative aldol-cyclization Sequence for the construction of substituted tetrahydrofurans was examined. The aldol condensation of alkenoates proceeded with alkylation at the alpha-position to generate homoallylic alcohol moieties. These compounds could be induced to cyclize under the influence of iodine via an endo mode. The stereoselectivity for the cyclization occurred in good to excellent fashion. X-ray crystal structure analysis of three of the tetrahydrofurans established unambiguously the product stereochemistry. This was: used to propose a transition structure for the cyclization which correctly predicts the observed product stereochemistry. By this method, virtually all the possible stereoisomers for the substituted tetrahydrofurans can be constructed by judicious choice of aldol product and/or olefin geometry.

  DOI：

  10.1021/jo00101a024

文献信息

• Tandem Aldol-Cyclization Sequence for the Construction of Cyclic Ethers. The Formation of Substituted Tetrahydrofurans
  作者：Paul Galatsis、Scott D. Millan、Patrik Nechala、George Ferguson

  DOI：10.1021/jo00101a024

  日期：1994.11

  The application of a tandem deconjugative aldol-cyclization Sequence for the construction of substituted tetrahydrofurans was examined. The aldol condensation of alkenoates proceeded with alkylation at the alpha-position to generate homoallylic alcohol moieties. These compounds could be induced to cyclize under the influence of iodine via an endo mode. The stereoselectivity for the cyclization occurred in good to excellent fashion. X-ray crystal structure analysis of three of the tetrahydrofurans established unambiguously the product stereochemistry. This was: used to propose a transition structure for the cyclization which correctly predicts the observed product stereochemistry. By this method, virtually all the possible stereoisomers for the substituted tetrahydrofurans can be constructed by judicious choice of aldol product and/or olefin geometry.