1-(2'-hydroxyphenyl)-1-propanol | 615563-76-3

• 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-(2'-hydroxyphenyl)-1-propanol
• 英文别名: (R)-1-(2-hydroxyphenyl)propan-1-one；(R)-2-(1'-hydroxypropyl)phenol；2-[(1R)-1-hydroxypropyl]phenol
• CAS: 615563-76-3
• 化学式: C₉H₁₂O₂
• 分子量: 152.193
• InChiKey: QWZBWROUTWGTDT-MRVPVSSYSA-N

物化性质

• 沸点：
  254.5±7.0 °C(Predicted)
• 密度：
  1.123±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (1'R,αS)-1-(α-methylbenzyloxy)-2-(1'-hydroxypropyl)benzene 在 30% Pd/C 、 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、405.33 kPa 条件下， 反应 16.0h， 以95%的产率得到1-(2'-hydroxyphenyl)-1-propanol
  参考文献：
  名称：

  一系列2-（1'-羟烷基）酚的立体发散性不对称合成

  摘要：

  （S）-α-甲基苄基作为手性助剂的使用允许三羰基铬络合的苯氧基环的非对映选择性的邻去质子化。当用醛处理所得的邻阴离子时，形成了两个相对较差博士的非对映异构体络合物，它们在新形成的苄基立体异构中心的构型上有所不同。但是，这两个邻-formylation接着用格氏试剂处理和邻酰基化，然后还原用超氢®被发现是完全非对映选择性的，从而可以在> 99：1 dr中获得相应苄醇配合物的差向异构体。随后氧化除去三羰基铬单元，然后裂解O -α-甲基苄基手性助剂，得到对映体纯的2-（1'-羟烷基）苯酚。按照该立体发散方法，可以从[（α-甲基苄氧基）苯] Cr（CO）3的单个对映体中获得产物的任一对映体。

  DOI：

  10.1016/j.tet.2010.07.058

文献信息

• α-Pinene-Based New Chiral Ionic Liquids and their Application as Phase Transfer Catalysts in Enantioselective Addition of Diethylzinc to Aldehydes
  作者：Sanjay Malhotra、Yun Wang、Vineet Kumar

  DOI：10.2174/157017809787893073

  日期：2009.4.1

  Amino alcohol functionalized new chiral ionic liquids have been synthesized from (+)-α-pinene, an easily available natural product. The effectiveness of these CILs as phase transfer catalysts (PTC) in enantioselective C-C bond formation has been demonstrated through the addition of diethylzinc to representative aldehydes, and the corresponding chiral alcohols with good yields and enantiomeric excess

  由（+）-α-pine烯（一种容易获得的天然产物）合成了氨基醇官能化的新型手性离子液体。这些CIL作为对映选择性CC键形成相转移催化剂（PTC）的有效性已通过将二乙基锌添加到代表性的醛中得到证明，并且获得了具有良好收率和对映体过量的相应手性醇。
• The synthesis of chiral amino diol tridentate ligands and their enantioselective induction during the addition of diethylzinc to aldehydes
  作者：An-lin Zhang、Li-wen Yang、Nian-fa Yang、Yan-ling Liu

  DOI：10.1016/j.tetasy.2013.11.007

  日期：2014.2

  A series of C2-symmetric chiral amino diol tridentate ligands 3a–g were prepared from achiral bulky organolithiums, achiral bulky primary amines, and optically active epichlorohydrin (ECH). The prepared C2-symmetric chiral amino diol tridentate ligands were capable of inducing enantioselectivity in the model reaction of aromatic and aliphatic aldehydes with diethylzinc with an ee of up to 96%. The

  由非手性庞大的有机锂，非手性庞大的伯胺和旋光表氯醇（ECH）制备了一系列C 2对称的手性氨基二醇三齿氨基配体3a – g。准备好的C 2芳族和脂族醛与二乙基锌的模型反应中，对称对称的手性氨基二醇三齿配体能够诱导对映选择性，ee最高可达96％。可以通过调节在手性配体的合成中使用的非手性试剂的空间位阻来调节对映选择性。加成产物的构型取决于氨基二醇配体的构型，可以通过在配体的制备过程中使用具有所需构型的ECH来根据需要简单地控制。
• A Green approach towards the synthesis of chiral alcohols using functionalized alginate immobilized Saccharomyces cerevisiae cells
  作者：Narmada Muthineni、Manikanta Swamy Arnipally、Sridhar Bojja、Harshadas Mitaram Meshram、Ajay Kumar Srivastava、Bhaskar Rao Adari

  DOI：10.1016/j.molcatb.2016.10.016

  日期：2016.12

  The stereochemistry of the drug molecule is gaining greater therapeutic importance and thus much attention was drawn in synthesis of chiral compounds by the pharmaceutical industry. In this study Saccharomyces cerevisiae cells immobilized on functionalized alginate beads, catalyze the bio-reduction of prochiral ketones 1a-12a to their corresponding chiral alcohols 1b-12b in higher yields of 60-99% and.excellent optical purity 75-97%. The synthesized chiral azido alcohols 10b-12b were further subjected to hydrogenation using Palladium(Pd) nanoparticles (<= 5 nm), to obtain chiral amino alcohols 10c-12c of therapeutic importance. Thus, a simple, green and inexpensive continuous chemo-enzymatic process has been developed in the synthesis of chiral alcohols/amino alcohols to enhance the scope of the methodology towards industrial application. (C) 2016 Elsevier B.V. All rights reserved.
• Chiral amide from (1S,2R)-(+)-norephedrine alkaloid in the enantioselective addition of diethylzinc to aryl and heteroaryl aldehydes
  作者：Nallamuthu Ananthi、Umesh Balakrishnan、Ajayan Vinu、Katsuhiko Ariga、Sivan Velmathi

  DOI：10.1016/j.tetasy.2009.07.011

  日期：2009.8

  Chiral amide synthesized from (1S,2R)-(+)-norephedrine and furoic acid was found to catalyze the enantioselective ethylation of aromatic and heteroaromatic aldehydes to secondary alcohols with 99.8% enantioselectivity at 0 degrees C without the addition of a promoter such as titanium tetraisopropoxide. (c) 2009 Elsevier Ltd. All rights reserved.
• The stereodivergent asymmetric synthesis of a range of 2-(1′-hydroxyalkyl)phenols
  作者：Stephen G. Davies、W. Ewan Hume、Paul M. Roberts、James E. Thomson

  DOI：10.1016/j.tet.2010.07.058

  日期：2010.10

  be completely diastereoselective, giving access to either epimer of the corresponding benzylic alcohol complexes in >99:1 dr. Subsequent oxidative removal of the chromium tricarbonyl unit, followed by cleavage of the O-α-methylbenzyl chiral auxiliary gives enantiopure 2-(1′-hydroxyalkyl)phenols. Following this stereodivergent procedure, either enantiomer of the product may be accessed from a single

  （S）-α-甲基苄基作为手性助剂的使用允许三羰基铬络合的苯氧基环的非对映选择性的邻去质子化。当用醛处理所得的邻阴离子时，形成了两个相对较差博士的非对映异构体络合物，它们在新形成的苄基立体异构中心的构型上有所不同。但是，这两个邻-formylation接着用格氏试剂处理和邻酰基化，然后还原用超氢®被发现是完全非对映选择性的，从而可以在> 99：1 dr中获得相应苄醇配合物的差向异构体。随后氧化除去三羰基铬单元，然后裂解O -α-甲基苄基手性助剂，得到对映体纯的2-（1'-羟烷基）苯酚。按照该立体发散方法，可以从[（α-甲基苄氧基）苯] Cr（CO）3的单个对映体中获得产物的任一对映体。