[(2S,4S)-4-phenoxypentan-2-yl] 2-diazoacetate | 322478-28-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: [(2S,4S)-4-phenoxypentan-2-yl] 2-diazoacetate
• CAS: 322478-28-4
• 化学式: C₁₃H₁₆N₂O₃
• 分子量: 248.282
• InChiKey: YZVCIMBCYTZSCL-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  [(2S,4S)-4-phenoxypentan-2-yl] 2-diazoacetate 在 dirhodium tetraacetate 作用下， 以 二氯甲烷 为溶剂， 生成 (3S,5S,8S)-3,5-dimethyl-2,6-dioxabicyclo[6.5.0]trideca-1(13),9,11-trien-7-one 、 (3S,5S,8R)-3,5-dimethyl-2,6-dioxabicyclo[6.5.0]trideca-1(13),9,11-trien-7-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：

  (4S,2R)-4-phenoxypentane-2-ol 在 对甲苯磺酰叠氮 、 三乙胺 、 苯甲酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 [(2S,4S)-4-phenoxypentan-2-yl] 2-diazoacetate
  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

文献信息

• Entropy-Controlled Asymmetric Synthesis. How Differential Activation Entropy Is Induced in Chiral Tethered Reactions
  作者：Takashi Sugimura、Kazutake Hagiya、Yasuhiro Sato、Takahiro Tei、Akira Tai、Tadashi Okuyama

  DOI：10.1021/ol006741m

  日期：2001.1.1

  [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.