(R)-methyl (E)-6-benzyloxy-4-hydroxy-2-hexenoate | 161814-44-4

• 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: (R)-methyl (E)-6-benzyloxy-4-hydroxy-2-hexenoate
• 英文别名: methyl (E,4R)-4-hydroxy-6-phenylmethoxyhex-2-enoate
• CAS: 161814-44-4
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: OLIUONNZMWDAHW-GWJCSSMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-methyl (E)-6-benzyloxy-4-hydroxy-2-hexenoate 以 吡啶 、 氯仿 为溶剂， 反应 80.0h， 生成 (2S,3S,3aR)-2-((R)-3-Benzyloxy-1-methanesulfonyloxy-propyl)-hexahydro-pyrrolo[1,2-b]isoxazole-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Diastereofacial Selectivity in the Cycloaddition of Nitrones to (E)-γ-Oxygenated α,β-Unsaturated Esters

  摘要：

  The 1,3-dipolar cycloadditions of nitrones 1 and 2 to a series of 1,2-disubstituted electron-deficient olefins bearing an allylic stereocenter, 4-8, are reported. The synlanti stereochemistry of the major endo adducts may be rationalized through the Houk transition-state model, but the possibility of intramolecular hydrogen bonding must be taken into account. In the case of the minor exo adducts the syn stereochemistry always predominates.

  DOI：

  10.1021/jo960960x
• 作为产物：
  描述：

  (R)-6-Benzyloxy-4-hydroxy-2-phenylselanyl-hexanoic acid methyl ester 在 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (R)-methyl (E)-6-benzyloxy-4-hydroxy-2-hexenoate
  参考文献：
  名称：

  Synthesis of (+)-Methyl (R,E)-6-Benzyloxy-4-hydroxy-2-hexenoate and Its Mesylate Derivative

  摘要：

  Methyl (E)-6-benzyloxy-4-hydroxy-2-hexenoate is prepared in both racemic and enantiopure form through reaction between (2-benzyloxy)ethyloxirane and the dianion of phenylselenoacetic acid followed by esterification with diazomethane, oxidation to the selenoxide and subsequent pyrolysis in 72% overall yield.

  DOI：

  10.1080/00397919508011364

文献信息

• Diastereofacial Selectivity in the Cycloaddition of Nitrones to (<i>E</i>)-γ-Oxygenated α,β-Unsaturated Esters
  作者：Félix Busqué、Pedro de March、Marta Figueredo、Josep Font、Montserrat Monsalvatje、Albert Virgili、Ángel Álvarez-Larena、Juan F. Piniella

  DOI：10.1021/jo960960x

  日期：1996.1.1

  The 1,3-dipolar cycloadditions of nitrones 1 and 2 to a series of 1,2-disubstituted electron-deficient olefins bearing an allylic stereocenter, 4-8, are reported. The synlanti stereochemistry of the major endo adducts may be rationalized through the Houk transition-state model, but the possibility of intramolecular hydrogen bonding must be taken into account. In the case of the minor exo adducts the syn stereochemistry always predominates.
• Synthesis of (+)-Methyl (<i>R,E</i>)-6-Benzyloxy-4-hydroxy-2-hexenoate and Its Mesylate Derivative
  作者：P. de March、M. Figueredo、J. Font、M. Monsalvatje

  DOI：10.1080/00397919508011364

  日期：1995.2

  Methyl (E)-6-benzyloxy-4-hydroxy-2-hexenoate is prepared in both racemic and enantiopure form through reaction between (2-benzyloxy)ethyloxirane and the dianion of phenylselenoacetic acid followed by esterification with diazomethane, oxidation to the selenoxide and subsequent pyrolysis in 72% overall yield.