3-(m-Methoxyphenyl)prop-1-yl diazoacetate | 171007-72-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(m-Methoxyphenyl)prop-1-yl diazoacetate
• 英文别名: 3-(3-methoxyphenyl)prop-1-yl diazoacetate；3-(3-Methoxyphenyl)propyl 2-diazoacetate
• CAS: 171007-72-0
• 化学式: C₁₂H₁₄N₂O₃
• 分子量: 234.255
• InChiKey: BARCUOQTGWQYQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  37.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(m-Methoxyphenyl)prop-1-yl diazoacetate 在 Rh2<4(S)-MPPIM>4 作用下， 以 二氯甲烷 为溶剂， 生成 4-<(3-methoxyphenyl)methyl>dihydrofuran-2(3H)-one
  参考文献：
  名称：

  Optimization of Enantiocontrol for Carbon-Hydrogen Insertion with Chiral Dirhodium(II) Carboxamidates. Synthesis of Natural Dibenzylbutyrolactone Lignans from 3-Aryl-1-propyl Diazoacetates in High Optical Purity

  摘要：

  DOI：

  10.1021/jo00126a002
• 作为产物：
  描述：

  3-(3-甲氧基苯基)丙酸 在 lithium hydroxide 、 lithium aluminium tetrahydride 、 sodium acetate 、 三乙胺 、 甲烷磺酰基叠氮化物 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 24.17h， 生成 3-(m-Methoxyphenyl)prop-1-yl diazoacetate
  参考文献：
  名称：

  Intramolecular Regioselective Insertion into Unactivated Prochiral Carbon−Hydrogen Bonds with Diazoacetates of Primary Alcohols Catalyzed by Chiral Dirhodium(II) Carboxamidates. Highly Enantioselective Total Synthesis of Natural Lignan Lactones

  摘要：

  Intramolecular insertion into unactivated prochiral C-H bonds of 3-aryl-1-propyl diazoacetates catalyzed by dirhodium(II) tetrakis[methyl 1-(3-phenyl propanoyl)imidazolidin-2-one-4(R or S)-carboxylate], Rh-2(4R-MPPIM)(4) or Rh-2(4S-MPPIM)(4), occurs in 91-96% ee and with virtually complete regiocontrol for the formation of beta-benzyl-gamma-butyrolactones. This methodology has been applied to the total synthesis of dibenzylbutyrolactone lignans (-)- and (+)-enterolactone, (-)- and (+)-hinokinin, and (+)-arctigenin from substituted cinnamic acids in 19-27% overall yields. Aryltetralin lignan (+)-isodeoxypodophyllotoxin was prepared from the reactant 3,4-(methylenedioxy)cinnamic acid in 36% yield overall, and the lactone precursor to (+)-isolauricerisinol was formed in 96.5% ee and 23% yield overall. Applications of the chiral Rh-2(MPPIM)4 catalysts to fully aliphatic systems resulting in the formation of beta-substituted-gamma-butyrolactones with high regiocontrol and with 93-96% ee have demonstrated the generality of this methodology. A model that provides accurate predictions of beta-substituted-gamma-butyrolactone absolute configurations in these asymmetric metal carbene transformations is described.

  DOI：

  10.1021/jo961607u