methyl 4-<2-hydroxy-5-(2-propenyloxy)phenyl>-7,9-dioxa-2-decenoate | 126666-04-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: methyl 4-<2-hydroxy-5-(2-propenyloxy)phenyl>-7,9-dioxa-2-decenoate
• 英文别名: methyl (E)-4-(2-hydroxy-5-prop-2-enoxyphenyl)-6-(methoxymethoxy)hex-2-enoate
• CAS: 126666-04-4
• 化学式: C₁₈H₂₄O₆
• 分子量: 336.385
• InChiKey: KZNOQSRKZRTNMT-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.78
• 重原子数：
  24.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  74.22
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 4-<2-hydroxy-5-(2-propenyloxy)phenyl>-7,9-dioxa-2-decenoate 在 哌啶 、 四氯化碳 、 potassium cyanide 、 三氟化硼乙醚 、 二异丁基氢化铝 、 三苯基膦 作用下， 以 甲醇 、 甲苯 、 乙腈 为溶剂， 反应 79.0h， 生成 (2R*,3S*)-3-<3-(2-chloroethyl)-2,3-dihydro-5-(2-propenyloxy)-2-benzofuranyl>-2-<(trimethylsilyl)oxy>-propanenitrile
  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：

  对苯醌 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 methyl 4-<2-hydroxy-5-(2-propenyloxy)phenyl>-7,9-dioxa-2-decenoate
  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