1-(benzyloxy)-3-phenylpropan-2-ol | 173917-50-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(benzyloxy)-3-phenylpropan-2-ol
• 英文别名: 1-Phenyl-3-phenylmethoxypropan-2-ol
• CAS: 173917-50-5
• 化学式: C₁₆H₁₈O₂
• 分子量: 242.318
• InChiKey: PYHFJKUJKSPIBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  1-(benzyloxy)-3-phenylpropan-2-ol 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 氢气 作用下， 以 正己烷 、 二氯甲烷 、 异丙醇 为溶剂， 生成 2-acetoxy-3-phenylpropan-1-ol
  参考文献：
  名称：

  Kinetic resolution of 2-acylated-1,2-diols by lipase-catalyzed enantiomer selective acylation

  摘要：

  Enantiomer selectivity of lipase catalyzed acylation of 2-acylated 1,2-diols was studied. First, acylation of 2-acetoxyheptan-1-ol rac-3b with vinyl acetate was investigated by varying the enzyme and the solvent, showing the highest enantiomer selectivity by using lipase from Pseudomonas fluorescens (PfL) in hexane-vinyl acetate (VA). We have found varying or even reversed enantiomer selectivity for different secondary acyl moieties in 2-acyloxyheptan-1-ols rac-3bA-F. Next, all six possible types of enantiomer selective biotransformations (hydrolysis of diacetate and the two kinds of monoacetetes; acylation of diol and the two kinds of monoacetates) were compared on two model diols rac-4b,d. Among the transformations investigated, acetylation of secondary monoacetates rac-3b,d showed the highest enantiomer selectivity. Finally, PfL catalyzed acetylations of several 2-acetylated 1,2-diols rac-3a-g were investigated under our optimum conditions. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00161-9
• 作为产物：
  描述：

  苄氧基乙醛 在 palladium dihydroxide aluminum oxide 、 氢气 作用下， 以 乙醇 为溶剂， 20.0~65.0 ℃ 、100.0 kPa 条件下， 生成 1-(benzyloxy)-3-phenylpropan-2-ol
  参考文献：
  名称：

  钯催化的苄基硝基键裂解：不对称合成的新机会。

  摘要：

  DOI：

  10.1002/anie.200604263

文献信息

• Glycerine and CeCl3˙7H2O: An Efficient and Recyclable Reaction Medium for Ring Opening of Epoxides with Thioamides and Amines
  作者：A. Narsaiah、Sachin Wadavrao、A. Reddy、J. Yadav

  DOI：10.1055/s-0030-1258366

  日期：2011.2

  Oxiranes undergo rapid ring-opening reaction with a range of thioamides and amines to afford the corresponding β-amino alcohol derivatives. The reactions were carried out using glycerine and cerium(III) chloride as a recyclable reaction medium. All the reactions were carried out at room temperature and the products were obtained in excellent yields.

  环氧乙烷与一系列硫酰胺和胺迅速发生开环反应，生成相应的β-氨基醇衍生物。反应采用甘油和氯化铈(III)作为可回收反应介质进行。所有反应均在室温下进行，产物收率极佳。
• Copper-catalyzed/mediated borylation reactions of epoxides with diboron reagents: access to β-hydroxyl boronic esters
  作者：Ebrahim-Alkhalil M. A. Ahmed、Xi Lu、Tian-Jun Gong、Zhen-Qi Zhang、Bin Xiao、Yao Fu

  DOI：10.1039/c6cc07924e

  日期：——

  We report the first copper-catalyzed/mediated borylative ring opening reaction of epoxides.

  我们报道了环氧的第一个铜催化/介导的硼化开环反应。
• Convenient Synthesis of Monoprotected 1,2-Diols
  作者：László Poppe、Katalin Recseg、Lajos Novák

  DOI：10.1080/00397919508011475

  日期：1995.12

  Abstract Reaction of the protected glycidol derivatives (1A-C) with a wide variety of Grignard reagents (2a-h) in the presence of catalytic amount of CuCN provided the corresponding monoprotected diol derivatives (3) in a highly regioselective manner.

  摘要 在催化量的 CuCN 存在下，受保护的缩水甘油衍生物 (1A-C) 与多种格氏试剂 (2a-h) 的反应以高度区域选择性的方式提供了相应的单保护二醇衍生物 (3)。
• Nickel-Catalyzed Regiodivergent Opening of Epoxides with Aryl Halides: Co-Catalysis Controls Regioselectivity
  作者：Yang Zhao、Daniel J. Weix

  DOI：10.1021/ja410704d

  日期：2014.1.8

  Epoxides are versatile intermediates in organic synthesis, but have rarely been employed in cross-coupling reactions. We report that bipyridine-ligated nickel can mediate the addition of functionalized aryl halides, a vinyl halide, and a vinyl triflate to epoxides under reducing conditions. For terminal epoxides, the regioselectivity of the reaction depends upon the cocatalyst employed. Iodide cocatalysis

  环氧化物是有机合成中的通用中间体，但很少用于交叉偶联反应。我们报告说，联吡啶连接的镍可以在还原条件下介导官能化芳基卤化物、乙烯基卤化物和乙烯基三氟甲磺酸酯与环氧化物的加成。对于末端环氧化物，反应的区域选择性取决于所用的助催化剂。碘化物共催化通过碘醇中间体在受阻较小的位置打开。Titanocene 共催化导致在更受阻的位置打开，大概是通过 Ti(III) 介导的自由基生成。1,2-二取代的环氧化物在两种条件下都打开，主要形成反式产物。
• Enantioselective Alkyl−Alkyl Suzuki Cross-Couplings of Unactivated Homobenzylic Halides
  作者：Bunnai Saito、Gregory C. Fu

  DOI：10.1021/ja8013677

  日期：2008.5.1

  effective method for asymmetric cross-couplings of unactivated alkyl electrophiles has been developed, specifically, a nickel-based catalyst for stereoconvergent Suzuki reactions of homobenzylic bromides with alkylboranes. To the best of our knowledge, there are no previous examples of enantioselective Suzuki couplings of alkyl electrophiles (activated or unactivated). Both of the catalyst components

  已开发出用于未活化的烷基亲电试剂的不对称交叉偶联的第一种有效方法，特别是用于高苄基溴与烷基硼烷的立体收敛 Suzuki 反应的镍基催化剂。据我们所知，之前没有烷基亲电试剂（活化或未活化）的对映选择性 Suzuki 偶联的例子。两种催化剂组分都是可商购的。