(2R,4R)-4-苯氧基-2-戊醇 | 724432-50-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: (2R,4R)-4-苯氧基-2-戊醇
• 英文名称: (2R,4R)-4-phenoxypentan-2-ol
• CAS: 724432-50-2
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: QACLFMNGNFHTBM-NXEZZACHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,4R)-4-苯氧基-2-戊醇 在 sodium hydroxide 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 水 为溶剂， 生成 (2S,4R)-4-phenoxypentan-2-ol
  参考文献：
  名称：

  Asymmetric meta-arene–alkene photocycloaddition controlled by a 2,4-pentanediol tether

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2004.03.017
• 作为产物：
  描述：

  (2S,4R)-4-phenoxypentan-2-ol 在 氢氧化钾 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 (2R,4R)-4-苯氧基-2-戊醇
  参考文献：
  名称：

  “Chiral Perturbation Factor” Approach Reveals Importance of Entropy Term in Stereocontrol of the 2,4-Pentanediol-Tethered Reaction

  摘要：

  The stereocontrol mechanism of the 2, 4-pentanediol (PD)-tethered reaction was studied in detail using a reaction system consisting of phenyl and rhodium carbenoid moieties. Different tethers were examined to analyze the effects of the methyl groups on the PD tether. Among the reactions with these tethers, the PD tether achieves an unmeasurably high stereoselectivity in a diastereomeric ratio of > 500. Another tether showing a high but measurable stereoselectivity in a ratio of 41 is mostly controlled by the entropy term. To clarify the role of the methyl groups on the chiral tethers, which are the origin of the stereocontrol, the "chiral perturbation factor" is introduced. This parameter is defined as the rate of a chiral reaction relative to that of an achiral reference reaction. By analyzing the temperature dependence of the chiral perturbation factors for different chiral-tethered reactions, high potentials of the PD-tethered reaction in its stereocontrol are concluded to be due to the entropy term.

  DOI：

  10.1021/jo025937s

文献信息

• 1,5-NAPHTHYRIDINE DERIVATIVE OR SALT THEREOF
  申请人：FUJIFILM Corporation

  公开号：EP2727920B1

  公开（公告）日：2016-11-02
• US8841456B2
  申请人：——

  公开号：US8841456B2

  公开（公告）日：2014-09-23
• [EN] 1,5-NAPHTHYRIDINE DERIVATIVE OR SALT THEREOF<br/>[FR] DÉRIVÉ DE 1,5-NAPHTYRIDINE OU SEL DE CELUI-CI
  申请人：FUJIFILM CORP

  公开号：WO2013018733A1

  公开（公告）日：2013-02-07

  　一般式［１］（式中、Ｒ１、Ｒ２、Ｒ３、Ｒ４及びＲ５は、水素原子又は－Ｌ－Ｚ（式中、Ｚは、非芳香族複素環基などを；Ｌは、単結合などを示す。）などを、Ｒ６は、－Ｌ－Ｚなどを、Ｒ７及びＲ８は、水素原子などを、Ｑは、酸素原子などを示す。）で表される１，５－ナフチリジン誘導体又はその塩は、ＰＩ３Ｋ－ＡＫＴ経路及びＲａｓ－Ｒａｆ－ＭＥＫ－ＥＲＫ経路に対し、優れた阻害活性を有し、ＰＩ３Ｋ－ＡＫＴ経路及びＲａｓ－Ｒａｆ－ＭＥＫ－ＥＲＫ経路が関与する疾患の予防又は治療などの処置に有用である。
• 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.
• “Chiral Perturbation Factor” Approach Reveals Importance of Entropy Term in Stereocontrol of the 2,4-Pentanediol-Tethered Reaction
  作者：Takahiro Tei、Yasuhiro Sato、Kazutake Hagiya、Akira Tai、Tadashi Okuyama、Takashi Sugimura

  DOI：10.1021/jo025937s

  日期：2002.9.1

  The stereocontrol mechanism of the 2, 4-pentanediol (PD)-tethered reaction was studied in detail using a reaction system consisting of phenyl and rhodium carbenoid moieties. Different tethers were examined to analyze the effects of the methyl groups on the PD tether. Among the reactions with these tethers, the PD tether achieves an unmeasurably high stereoselectivity in a diastereomeric ratio of > 500. Another tether showing a high but measurable stereoselectivity in a ratio of 41 is mostly controlled by the entropy term. To clarify the role of the methyl groups on the chiral tethers, which are the origin of the stereocontrol, the "chiral perturbation factor" is introduced. This parameter is defined as the rate of a chiral reaction relative to that of an achiral reference reaction. By analyzing the temperature dependence of the chiral perturbation factors for different chiral-tethered reactions, high potentials of the PD-tethered reaction in its stereocontrol are concluded to be due to the entropy term.