(2R)-1-phenylbutan-2-ol | 29393-19-9

• 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: (2R)-1-phenylbutan-2-ol
• 英文别名: (R)-1-phenyl-2-butanol；(R)-1-phenylbutan-2-ol；1-phenyl-2-butanol
• CAS: 29393-19-9
• 化学式: C₁₀H₁₄O
• 分子量: 150.221
• InChiKey: LYUPJHVGLFETDG-SNVBAGLBSA-N

物化性质

• 沸点：
  226.6±0.0 °C(Predicted)
• 密度：
  0.980±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  (2R)-1-phenylbutan-2-ol 在 NADPH 、 nicotinamide adenine dinucleotide phosphate 、 W₁₁₀A/I₈₆A/C₂₉₅A TeSADH 作用下， 以 乙腈 为溶剂， 生成 1-苯基-2-丁酮
  参考文献：
  名称：

  Thermoanaerobacter ethanolicus secondary alcohol dehydrogenase mutants with improved racemization activity

  摘要：

  Controlled racemization of enantiopure alcohols is a key step in dynamic kinetic resolution. We recently reported the racemization of enantiopure phenyl-ring-containing alcohols using W110A Thermoanaerobacter ethanolicus secondary alcohol dehydrogenase (W110A TeSADH), which relies on selectivity mistakes. Trp-110 lines the large pocket of the active site of TeSADH, which allows W110A TeSADH mutant to accommodate phenyl-ring-containing substrates in Prelog mode, albeit with selectivity mistakes. Here, we report the racemization of enantiopure phenyl-ring-containing alcohols using several Trp-110 mutants of TeSADH in the presence of the oxidized and reduced forms of nicotinamide adenine dinucleotide. We observed a noticeable enhancement in racemization efficiency when W110G TeSADH was used compared with W110Q, W110M, W110L, W110I, and W110V. This observation was anticipated because the W110G mutation is expected to open the large pocket of the active site to a greater extent compared to other mutants of TeSADH at W110. Both enantiomers of 1-phenyl-2-propanol and 4-phenyl-2-butanol were fully racemized by W110G TeSADH. We also constructed a triple mutant of TeSADH, W110A/186A/C295A, by site-directed mutagenesis with the aim of opening the two pockets of the active site of TeSADH. The W110A/186A/C295A mutant was employed to racemize enantiopure phenyl-ring-containing alcohols. The current study demonstrates that W110G and W110A/186A/C295A TeSADH are more efficient catalysts for the racemization of enantiopure secondary alcohols than the previously reported mutant W110A TeSADH [6]. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2015.02.012
• 作为产物：
  描述：

  1-苯基-2-丁酮 在 Mucor racemsous 7924 作用下， 以 various solvent(s) 为溶剂， 以34%的产率得到(2R)-1-phenylbutan-2-ol
  参考文献：
  名称：

  使用目标微生物库快速鉴定对映选择性酮还原

  摘要：

  调查了大约300个微生物的集合，以通过对映选择性还原一系列烷基芳基酮来生成手性仲醇的能力。将证明在还原模型酮中有用的微生物培养物排列在多孔板中，并用于快速鉴定能够产生手性醇的特定生物，这些手性醇在几种候选药物的合成中用作中间体。显示大约60种培养物可选择性还原提供R和S的各种酮相应醇的对映体含量为92–99％ee，1-4 g / L时产率高达95％。还报道了基于外消旋醇的选择性微生物氧化的手性醇的替代方法。该研究为通过选择性微生物生物转化产生手性醇提供了有用的参考。

  DOI：

  10.1016/j.tet.2003.10.123

文献信息

• Mechanistic Studies of the Copper-Catalyzed Electrophilic Amination of Diorganozinc Reagents and Development of a Zinc-Free Protocol
  作者：Matthew J. Campbell、Jeffrey S. Johnson

  DOI：10.1021/ol0702829

  日期：2007.4.1

  mechanism for the copper-catalyzed amination of diorganozinc reagents by O-benzoyl-N,N-dialkylhydroxylamines is supported by following stereochemically defined organometallics through the reaction and by employing the endocyclic restriction test. A copper-catalyzed electrophilic amination of organomagnesium compounds is also described in which the use of zinc halides has been eliminated.

  [反应：见正文]通过遵循立体化学定义的有机金属化合物通过反应并采用环内限制性试验，可以支持SN2机制，以O-苯甲酰基-N，N-二烷基羟胺的铜催化胺化二有机锌试剂。还描述了铜催化的有机镁化合物的亲电子胺化，其中已经消除了卤化锌的使用。
• d-Penicillamine and l-cysteine derived thiazolidine catalysts: an efficient approach to both enantiomers of secondary alcohols
  作者：M. Elisa Silva Serra、Dora Costa、Dina Murtinho、Nélia C.T. Tavares、Teresa M.V.D. Pinho e Melo

  DOI：10.1016/j.tet.2016.08.036

  日期：2016.9

  d-Penicillamine derived thiazolidine ligands were prepared in a two-step synthetic sequence and used in the enantioselective alkylation of a variety of aromatic aldehydes with diethylzinc at room temperature. Excellent ee, up to >99%, and nearly complete conversions were observed. Structurally analogous l-cysteine derived thiazolidine ligands were also synthesized and tested for comparative purposes

  d-青霉胺衍生的噻唑烷配体以两步合成顺序制备，并在室温下用于各种芳香醛与二乙基锌的对映选择性烷基化。优秀的ee，高达> 99％，并且观察到几乎完全的转换。还合成了结构相似的1-半胱氨酸衍生的噻唑烷配体，并进行了比较试验，结果显示出很好的选择性，尽管选择性略低，最高可达89％。两种噻唑烷的组合使用构成合成（S）和（R）手性仲醇的对映异构体，从而引出了无数有用的具有相反绝对构型的旋光产物。
• Expanding the Substrate Specificity of <i>Thermoanaerobacter pseudoethanolicus</i> Secondary Alcohol Dehydrogenase by a Dual Site Mutation
  作者：Musa M. Musa、Odey Bsharat、Ibrahim Karume、Claire Vieille、Masateru Takahashi、Samir M. Hamdan

  DOI：10.1002/ejoc.201701351

  日期：2018.2.14

  The authors acknowledge the support provided by the Deanship of Scientific Research (DSR) at King Fahd University of Petroleum and Minerals (KFUPM) for funding this work under project number IN151032. They also acknowledge the supported by baseline research fund to S.M.H. by King Abdullah University of Science and Technology.

  作者感谢法赫德国王石油和矿产大学 (KFUPM) 科学研究院长 (DSR) 为在项目编号 IN151032 下资助这项工作提供的支持。他们还感谢阿卜杜拉国王科技大学对 SMH 的基线研究基金的支持。
• Iron(II) Complexes Containing Unsymmetrical P–N–P′ Pincer Ligands for the Catalytic Asymmetric Hydrogenation of Ketones and Imines
  作者：Paraskevi O. Lagaditis、Peter E. Sues、Jessica F. Sonnenberg、Kai Yang Wan、Alan J. Lough、Robert H. Morris

  DOI：10.1021/ja4082233

  日期：2014.1.29

  hydrogenation using iron. The complexes are prepared in two steps: (1) a one-pot reaction of phosphonium dimers ([cyclo-(PR2CH2CH(OH)(-))2][Br]2), KOtBu, FeBr2, and Ph2PCH2CH2NH2 (or (S,S)-Ph2PCH(Ph)CH(Me)NH2 for the enantiopure complex) in THF under a CO atmosphere to produce the complexes cis- and trans-[Fe(Br)2(CO)(P-CH═N-P')]; (2) the reaction of these with AgBF4 under CO(g) to afford the dicarbonyl complexes

  在用 LiAlH4 和醇处理后，新的二羰基铁络合物形成反式-[Fe(Br)(CO)2(P-CH=N-P')][BF4]（其中 P-CH=NP' = R2PCH2CH =NCH2CH2PPh2 和 R = Cy 或 iPr 或 P-CH=NP' = (S,S)-Cy2PCH2CH=NCH(Me)CH(Ph)PPh2) 是在 50°添加 KOtBu 的 THF 溶剂中酮加氢的催化剂C 和 5 个大气压的 H2。R = Ph 的配合物没有活性。使用 enantiopure 复合物，在 TOF 高达 2000 h(-1)、TON 高达 5000 的范围内，以高达 85% (S) 的对映体过量生产醇。活化的亚胺在 TOF 20 h(-1) 和 TON 99 下以 90% ee 氢化成胺。这是使用铁的不对称压力氢化的重大进步。配合物分两步制备：(1) 鏻二聚体 ([环-(PR2CH2CH(OH)(-)
• A Chiral Metal-Organic Material that Enables Enantiomeric Identification and Purification
  作者：Shi-Yuan Zhang、Cheng-Xiong Yang、Wei Shi、Xiu-Ping Yan、Peng Cheng、Lukasz Wojtas、Michael J. Zaworotko

  DOI：10.1016/j.chempr.2017.07.004

  日期：2017.8

  coupled with the thermal and hydrolytic stability of CMOM-3S, these features mean that a coated fused silica capillary column in which CMOM-3S serves as a CSP is both more versatile and more robust than three benchmark commercial columns. That the enantiomer with the longer GC retention time is consistently captured in CCS experiments enables CMOM-3S to serve as a powerful tool to enable both chiral purification

  我们表明，CMOM-3S是一种以前未曾报道过的具有固有手性的多孔晶体金属有机材料，可作为通用手性结晶海绵（CCS）和用于气相色谱（GC）的手性固定相（CSP）。CMOM-3S的特性是通过与模拟酶结合位点的适应性分子识别位点相连的纳米级通道实现的。此外，CMOM-3S由廉价的组件组成，易于制备，并且仅需痕量分析物。与CMOM-3S的热稳定性和水解稳定性相结合时，这些功能意味着以CMOM-3S用作CSP的涂层熔融石英毛细管色谱柱比三种基准商业色谱柱具有更多的通用性和更强的耐用性。