(R)-4-phenoxybutan-2-ol | 322478-50-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (R)-4-phenoxybutan-2-ol
• 英文别名: (2R)-4-phenoxybutan-2-ol
• CAS: 322478-50-2
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: WBTFUMUXXHWTLD-SECBINFHSA-N

物化性质

• 沸点：
  260.0±13.0 °C(Predicted)
• 密度：
  1.033±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  (R)-4-phenoxybutan-2-ol 在 sodium tetrahydroborate 、 羰基镁 、 三甲胺盐酸盐 、 三乙胺 作用下， 以 1,4-二氧六环 、 2-甲基-2-丁醇 、 二氯甲烷 为溶剂， 50.0 ℃ 、1.01 MPa 条件下， 反应 20.0h， 生成 (S)-2-methyl-4-phenoxybutan-1-ol
  参考文献：
  名称：

  锰催化的甲苯磺酸烷基酯的立体特异性羟甲基化。

  摘要：

  描述了使用便宜的第一行催化剂开发烷基甲苯磺酸酯的立体有针对性的羟甲基化。该转化在温和条件下以低压进行，以递送作为产物的同系醇。从容易获得的仲烷基底物上获得具有高对映体特异性的手性，非外消旋的β-支链伯醇。将反应体系的简单修改还允许访问α- ð 2醇。这些研究使用阴离子金属羰基催化，以从一氧化碳中获得具有挑战性的羟甲基阴离子的合成等价物。

  DOI：

  10.1021/acs.orglett.9b03706
• 作为产物：
  描述：

  2-(((R)-4-phenoxybutan-2-yl)oxy)tetrahydro-2H-pyran 在 甲醇 、 4-甲基苯磺酸吡啶 作用下， 以84%的产率得到(R)-4-phenoxybutan-2-ol
  参考文献：
  名称：

  锰催化的甲苯磺酸烷基酯的立体特异性羟甲基化。

  摘要：

  描述了使用便宜的第一行催化剂开发烷基甲苯磺酸酯的立体有针对性的羟甲基化。该转化在温和条件下以低压进行，以递送作为产物的同系醇。从容易获得的仲烷基底物上获得具有高对映体特异性的手性，非外消旋的β-支链伯醇。将反应体系的简单修改还允许访问α- ð 2醇。这些研究使用阴离子金属羰基催化，以从一氧化碳中获得具有挑战性的羟甲基阴离子的合成等价物。

  DOI：

  10.1021/acs.orglett.9b03706

文献信息

• Cobalt-Catalyzed Carbonylative Cross-Coupling of Alkyl Tosylates and Dienes: Stereospecific Synthesis of Dienones at Low Pressure
  作者：Brendon T. Sargent、Erik J. Alexanian

  DOI：10.1021/jacs.7b07983

  日期：2017.9.13

  carbonylative coupling of alkyl tosylates and dienes producing enantioenriched dienones. This catalytic process proceeds under low pressure and mild conditions using a simple cobalt catalyst and extends to diverse tosylate and diene coupling partners. The transformation constitutes a unique, convergent approach to the asymmetric synthesis of valuable carbonyl compounds from easily accessed starting materials

  尽管烷基亲电子试剂的有机金属交叉偶联取得了进展，但手性非外消旋底物的立体选择性反应很少。在本文中，我们报道了烷基对甲苯磺酸酯和二烯产生对映体富集的二烯酮的立体有择的羰基化偶联。该催化过程使用简单的钴催化剂在低压和温和条件下进行，并扩展到各种甲苯磺酸酯和二烯偶联伙伴。该转化构成了一种独特的，收敛的方法，可以从易于获取的起始原料中不对称地合成有价值的羰基化合物。
• 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.
• “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.
• Stereocontrolled intramolecular meta-arene–alkene photocycloaddition reactions using chiral tethers: efficiency of the tether derived from 2,4-pentanediol
  作者：Takashi Sugimura、Akiko Yamasaki、Tadashi Okuyama

  DOI：10.1016/j.tetasy.2004.11.086

  日期：2005.2

  Photochemical reactions of substrates consisting of phenyl and vinyl groups, which are tethered with a chiral diol, resulted in intramolecular meta-arene-alkene cycloaddition; the reaction efficiency as well as the stereoselectivity was studied. 1,3-Butanediol, 2-substituted 1,3-propanediols, 2-methyl-2,4-penetanediol, and 2,6-dimethyl-3,5-heptanediol were employed as tethers, and the results are compared with those obtained with 2,4-pentanediol (PD) tether, which are known to show high stereoselectivity and moderate efficiency. All the reactions with the lower analogues were less efficient than with PD, although one of the butanediol-tethered reactions afforded a single stereoisomer as PD did. The dimethylheptanediol tether showed similar efficiency but lower stereoselectivity than PD. The results suggest that the PD tether has an optimized structure having a proper flexibility. (C) 2004 Elsevier Ltd. All rights reserved.
• Manganese-Catalyzed Stereospecific Hydroxymethylation of Alkyl Tosylates
  作者：Hannah Shenouda、Erik J. Alexanian

  DOI：10.1021/acs.orglett.9b03706

  日期：2019.11.15

  The development of a stereospecific hydroxymethylation of alkyl tosylates using an inexpensive, first-row catalyst is described. The transformation proceeds under mild conditions with low pressure to deliver homologated alcohols as products. Chiral, nonracemic β-branched primary alcohols are obtained with high enantiospecificity from easily accessed secondary alkyl substrates. Simple modification of

  描述了使用便宜的第一行催化剂开发烷基甲苯磺酸酯的立体有针对性的羟甲基化。该转化在温和条件下以低压进行，以递送作为产物的同系醇。从容易获得的仲烷基底物上获得具有高对映体特异性的手性，非外消旋的β-支链伯醇。将反应体系的简单修改还允许访问α- ð 2醇。这些研究使用阴离子金属羰基催化，以从一氧化碳中获得具有挑战性的羟甲基阴离子的合成等价物。