(S)-1-phenylpentan-3-ol | 71747-37-0

• 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: (S)-1-phenylpentan-3-ol
• 英文别名: (S)-1-phenyl-3-pentanol；1-phenyl-3-pentanol；1-phenylpentan-3-ol；(S)-5-phenylpentan-3-ol；(3S)-1-phenylpentan-3-ol
• CAS: 71747-37-0
• 化学式: C₁₁H₁₆O
• 分子量: 164.247
• InChiKey: NFHFXJDPAATBQI-NSHDSACASA-N

物化性质

• 熔点：
  38°C
• 沸点：
  251.73°C (rough estimate)
• 密度：
  0.9687

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-1-phenylpentan-3-ol 在 吡啶 、 4-二甲氨基吡啶 、 三氟化硼乙醚 作用下， 反应 20.0h， 生成 ethyl (3R,4R,5S)-4-acetamido-5-azido-3-[(3S)-1-phenylpentan-3-yl]oxycyclohexene-1-carboxylate
  参考文献：
  名称：

  Structure−Activity Relationship Studies of Novel Carbocyclic Influenza Neuraminidase Inhibitors

  摘要：

  A series of influenza neuraminidase inhibitors with the cyclohexene scaffold containing lipophilic side chains have been synthesized anti evaluated for influenza A and B neuraminidase inhibitory activity. The size and geometry of side chains have been modified systematically in order to investigate structure-activity relationships of this class of compounds. The X-ray crystal structures of several analogues complexed with neuraminidase revealed that the lipophilic side chains bound to the hydrophobic pocket consisted of Glu276, Ala246, Arg224, and Ile222 of the enzyme active site. The structure-activity relationship studies of this series have also demonstrated remarkably different inhibitory potency between influenza A and B neuraminidase. This indicated that the lipophilic side chains had quite different hydrophobic interactions with influenza A and B neuraminidase despite their complete homology in the active site. Influenza B neuraminidase appeared to be much more sensitive toward the increased steric bulkiness of inhibitors compared to influenza A neuraminidase. From the extensive structure-activity relationship investigation reported in this article, GS 4071 emerged as one of the most potent influenza neuraminidase inhibitors against both influenza A and B strains.

  DOI：

  10.1021/jm980162u
• 作为产物：
  描述：

  苯甲酰乙酸 在 tris-(dibenzylideneacetone)dipalladium(0) 、 palladium 10% on activated carbon 、 氢气 、 (-)-1(R),2(R)-bis<2'-(diphenylphosphino)benzamido>-1,2-diphenylethane 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， -15.0~20.0 ℃ 、101.33 kPa 条件下， 反应 22.0h， 生成 (S)-1-phenylpentan-3-ol
  参考文献：
  名称：

  钯催化 β-酮酸不对称脱羧加成到杂原子取代的艾伦

  摘要：

  报道了 Pd 催化的 β-酮酸与杂原子取代的丙二烯的不对称加成反应。该反应通过分支选择性脱羧烯丙基化途径以不对称方式生成 β 取代的酮。该反应适用于各种烷氧基丙二烯以及酰胺基丙二烯。

  DOI：

  10.1002/anie.202107990

文献信息

• Improved method for the conversion of pinacolboronic esters into trifluoroborate salts: facile synthesis of chiral secondary and tertiary trifluoroborates
  作者：Viktor Bagutski、Abel Ros、Varinder K. Aggarwal

  DOI：10.1016/j.tet.2009.10.002

  日期：2009.11

  A general method for the preparation of virtually any potassium trifluoroborate salt from the corresponding pinacolboronic ester is reported. Thus, conditions for an azeotropic removal of pinacol from the reaction mixture were found to afford the desired potassium trifluoroborates of sufficient purity (>95%) in nearly quantitative yields irrespective of the nature of the product. The utility of this

  报道了从相应的频哪醇硼酸酯制备几乎任何三氟硼酸钾盐的通用方法。因此，发现从反应混合物中共沸除去频哪醇的条件以几乎定量的产率提供了具有足够纯度（＞ 95％）的所需三氟硼酸钾，而与产物的性质无关。通过制备大量对映体富集的仲和叔三氟硼酸钾说明了该方法的实用性。
• Enantioselective addition of diethylzinc to aldehydes catalyzed by titanium(IV) complexes of N-sulfonylated amino alcohols with two stereogenic centers
  作者：Jing-Song You、Ming-Yuan Shao、Han-Mou Gau

  DOI：10.1016/s0957-4166(01)00522-5

  日期：2001.11

  Bidentate N-sulfonylated amino alcohols with one or two stereogenic centers were prepared and applied as chiral ligands in the titanium(IV)-catalyzed asymmetric addition of diethylzinc to aldehydes, affording excellent enantioselectivities of up to 98% e.e.

  制备具有一个或两个立体生成中心的双齿N-磺酰化氨基醇，并将其用作手性配体，用于钛（IV）催化的二乙基锌与醛的不对称加成中，可提供高达98％ee的出色对映选择性
• Polystyrene-Supported (2<i>S</i>)-(−)-3-<i>exo</i>-Piperazinoisoborneol: An Efficient Catalyst for the Batch and Continuous Flow Production of Enantiopure Alcohols
  作者：Laura Osorio-Planes、Carles Rodríguez-Escrich、Miquel A. Pericàs

  DOI：10.1021/ol300415f

  日期：2012.4.6

  (PS-PIB) of 3-exo-morpholinoisoborneol (MIB), designed for increased chemical stability, has been synthesized and used as a ligand in the asymmetric alkylation of aldehydes with Et2Zn. The supported ligand turned out to be highly active and enantioselective for a broad scope of substrates (92–99% ee), allowing repeated recycling. A single-pass, continuous flow process implemented with PS-PIB shows only

  为提高化学稳定性而设计的3-外-吗啉代异冰片醇（MIB）的聚苯乙烯支撑类似物（PS-PIB）已合成，并用作醛与Et 2 Zn的不对称烷基化反应中的配体。结果表明，受支持的配体对多种底物（92–99％ee）具有很高的活性和对映选择性，可以重复使用。使用PS-PIB实施的单程连续流工艺在运行30小时后，转化率仅略有下降。
• The synthesis of new oxazoline-containing bifunctional catalysts and their application in the addition of diethylzinc to aldehydes
  作者：Vincent Coeffard、Helge Müller-Bunz、Patrick J. Guiry

  DOI：10.1039/b822580j

  日期：——

  bifunctional catalysts is reported employing a microwave-assisted Buchwald–Hartwig aryl amination as the key step. Covalent attachment of 2-(o-aminophenyl)oxazolines and pyridine derivatives generated in good-to-high yields a series of ligands in two or three steps in which each part was altered independently to tune the activity and the selectivity of the corresponding catalysts. These catalysts prepared

  据报道，采用微波辅助的Buchwald-Hartwig芳基胺化法作为关键步骤，可以直接制备新型的含恶唑啉的新型模块式双功能催化剂。2-（邻氨基苯基）恶唑啉和吡啶衍生物的共价连接以高到高的方式生成，分两步或三步产生一系列配体，其中每个部分独立地改变以调节活性和相应催化剂的选择性。这些原位制备的催化剂随后用于不对称加成二乙基锌生成各种醛，生成对映体选择性高达68％的相应醇。还提出了一种基于相关X射线晶体结构的过渡态模型来解释观察到的立体选择性。
• Switching of Enantioselectivity in the Catalytic Addition of Diethylzinc to Aldehydes by Regioisomeric Chiral 1,3-Amino Sulfonamide Ligands
  作者：Takuji Hirose、Kazuyuki Sugawara、Koichi Kodama

  DOI：10.1021/jo200834n

  日期：2011.7.1

  Twenty chiral 1,3-amino sulfonamides of two classes (2a–i and 3a–k) have been prepared from (−)-cis-2-benzamidocyclohexanecarboxylic acid (1) and studied as ligands for catalytic enantioselective addition of Et2Zn to a variety of aromatic and aliphatic aldehydes. The ligands 2 and 3 are regioisomers in which the position of the amine and sulfonamide groups is exchanged. Each class of ligands with the

  从（-）-顺式-2-苯甲酰胺基环己烷羧酸（1）制备了两类（2a – i和3a – k）的二十种手性1,3-氨基磺酰胺，并研究了其作为Et 2 Zn催化对映选择性加成的配体。各种芳香族和脂肪族醛。配体2和3是区域异构体，其中胺和磺酰胺基团的位置被交换。显示具有相同手性的每一类配体提供具有相反立体化学的仲醇。结构调查表明，叔氨基和p的组合-甲苯磺酰脲基对反应最有效。通过优化结构和反应条件，最佳配体定量提供了两种对映体仲醇，对（S）-和（R）-对映体的对映体选择性良好，对映体选择性分别高达94％和98％ee 。