(2R,4S)-4-m-Tolyloxy-pentan-2-ol | 322478-46-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2R,4S)-4-m-Tolyloxy-pentan-2-ol
• CAS: 322478-46-6
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: AVONFXUXUDADOH-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.53
• 重原子数：
  14.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (2R,4S)-4-m-Tolyloxy-pentan-2-ol 在 对甲苯磺酰叠氮 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 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
• 作为产物：
  描述：

  (2R,4R)-pentanediol 、 间甲酚 在 dialkyl azodicarboxylate 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 以90.2%的产率得到(2R,4S)-4-m-Tolyloxy-pentan-2-ol
  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

• Asymmetric meta-arene–alkene photocycloaddition controlled by a 2,4-pentanediol tether
  作者：Kazutake Hagiya、Akiko Yamasaki、Tadashi Okuyama、Takashi Sugimura

  DOI：10.1016/j.tetasy.2004.03.017

  日期：2004.5

  Photo-irradiation of a substrate having phenyl and vinyl groups resulted in a stereocontrolled meta-arene-alkene cycloaddition when the two groups were connected by a chiral 2,4-pentanediol tether. The regioselectivity during the ring closing step after the initial addition was dependent on the stereochemistry of the tether and the photolysis conditions. The substrate bearing a p-tolyl or 3,5-xylyl group instead of the phenyl also underwent strict stereocontrolled addition. In the case of the o- and m-tolyl substrates, the regioselectivity due to the unsymmetric substitution of the arene moiety was also fully controlled. (C) 2004 Elsevier Ltd. All rights reserved.