Methyl (2S*,3S*)-4-(2 hydroxy-5-(2-propenyloxy)phenyl)-2-octenoate | 126666-03-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: Methyl (2S*,3S*)-4-(2 hydroxy-5-(2-propenyloxy)phenyl)-2-octenoate
• 英文别名: methyl (E)-4-(2-hydroxy-5-prop-2-enoxyphenyl)oct-2-enoate
• CAS: 126666-03-3
• 化学式: C₁₈H₂₄O₄
• 分子量: 304.386
• InChiKey: LUGYNIWANQKHPL-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.39
• 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：

  Methyl (2S*,3S*)-4-(2 hydroxy-5-(2-propenyloxy)phenyl)-2-octenoate 在 palladium on activated charcoal 哌啶 、 氢气 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 甲醇 、 苯 为溶剂， 反应 24.25h， 生成 ((2S,3S)-5-Allyloxy-3-butyl-2,3-dihydro-benzofuran-2-yl)-acetic acid methyl ester
  参考文献：
  名称：

  Controlling the stereochemistry of the ring junction in hexahydrodibenzofurans

  摘要：

  The 8-hydroxy-1,2,3,4,4a,9b-hexahydrodibenzofuran-3-one formed during the acid-catalyzed rearrangement of 1,4,4a,8a-tetrahydro-1-methoxy-1,4-ethanonaphthalene-5,8-dione is, contrary to published reports, exclusively the cis isomer by X-ray crystallography. The stereochemical outcome of this intramolecular Michael addition results from the cyclid nature of the alpha,beta-unsaturated carbonyl, since, in acyclic systems, the addition product is a trans-2,3-disubstituted 2,3-dihydrobenzofuran. The trans relationship of the 2- and 3-substituents in the acyclic system was confirmed by annulation to the trans-8-hydroxy-1,2,3,4,4a,9b-hexahydrodibenzofuran-3-one and X-ray crystallographic analysis of the 3-cyanohydrin.

  DOI：

  10.1021/jo00021a042
• 作为产物：
  描述：

  正己醛 以 四氢呋喃 为溶剂， 生成 Methyl (2S*,3S*)-4-(2 hydroxy-5-(2-propenyloxy)phenyl)-2-octenoate
  参考文献：
  名称：

  Controlling the stereochemistry of the ring junction in hexahydrodibenzofurans

  摘要：

  The 8-hydroxy-1,2,3,4,4a,9b-hexahydrodibenzofuran-3-one formed during the acid-catalyzed rearrangement of 1,4,4a,8a-tetrahydro-1-methoxy-1,4-ethanonaphthalene-5,8-dione is, contrary to published reports, exclusively the cis isomer by X-ray crystallography. The stereochemical outcome of this intramolecular Michael addition results from the cyclid nature of the alpha,beta-unsaturated carbonyl, since, in acyclic systems, the addition product is a trans-2,3-disubstituted 2,3-dihydrobenzofuran. The trans relationship of the 2- and 3-substituents in the acyclic system was confirmed by annulation to the trans-8-hydroxy-1,2,3,4,4a,9b-hexahydrodibenzofuran-3-one and X-ray crystallographic analysis of the 3-cyanohydrin.

  DOI：

  10.1021/jo00021a042