Diazo-acetic acid (1R,3S)-1-methyl-3-m-tolyloxy-butyl ester | 322478-32-0

• 英文名称: Diazo-acetic acid (1R,3S)-1-methyl-3-m-tolyloxy-butyl ester
• 英文别名: [(2R,4S)-4-(3-methylphenoxy)pentan-2-yl] 2-diazoacetate
• CAS: 322478-32-0
• 化学式: C₁₄H₁₈N₂O₃
• 分子量: 262.309
• InChiKey: NMQCTXMMVQAJAD-NWDGAFQWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  Diazo-acetic acid (1R,3S)-1-methyl-3-m-tolyloxy-butyl ester 在 dirhodium tetraacetate 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到(7S,9R,11aS)-4,7,9-Trimethyl-8,9-dihydro-7H,11aH-6,10-dioxa-cycloheptacycloocten-11-one
  参考文献：
  名称：

  Entropy-Controlled Asymmetric Synthesis. How Differential Activation Entropy Is Induced in Chiral Tethered Reactions

  摘要：

  [GRAPHICS]Kinetic measurements to determine effective molarities of intramolecular reactions using 2,4-pentanediol and related tethers showed that methyl groups on the tether accelerate the major diastereomeric process but decelerate the minor process. The efficient promotion of stereocontrol is suggested to be due to chiral perturbation of the reaction rate through the entropy term, The conformation of the encounter complex of the reagent and reactant moieties was deduced by stereochemical analysis of the intramolecular adducts.

  DOI：

  10.1021/ol006741m
• 作为产物：
  描述：

  3-Oxo-butyric acid (1R,3S)-1-methyl-3-m-tolyloxy-butyl ester 在 对甲苯磺酰叠氮 、 三乙胺 作用下， 以 乙腈 为溶剂， 以72.6%的产率得到Diazo-acetic acid (1R,3S)-1-methyl-3-m-tolyloxy-butyl ester
  参考文献：
  名称：

  Entropy-Controlled Asymmetric Synthesis. How Differential Activation Entropy Is Induced in Chiral Tethered Reactions

  摘要：

  [GRAPHICS]Kinetic measurements to determine effective molarities of intramolecular reactions using 2,4-pentanediol and related tethers showed that methyl groups on the tether accelerate the major diastereomeric process but decelerate the minor process. The efficient promotion of stereocontrol is suggested to be due to chiral perturbation of the reaction rate through the entropy term, The conformation of the encounter complex of the reagent and reactant moieties was deduced by stereochemical analysis of the intramolecular adducts.

  DOI：

  10.1021/ol006741m