(S)-2-甲基-2-苯氧基甲醇 | 87860-35-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: (S)-2-甲基-2-苯氧基甲醇
• 英文名称: (S)-2-Methyl-2-phenoxy carbinolcid
• 英文别名: (S)-2-phenoxy-1-propanol；(S)-2-phenoxypropan-1-ol；2-phenoxy-1-propanol；2-phenoxypropan-1-ol；(2S)-2-phenoxypropan-1-ol
• CAS: 87860-35-3
• 化学式: C₉H₁₂O₂
• 分子量: 152.193
• InChiKey: LOJHHQNEBFCTQK-QMMMGPOBSA-N

物化性质

• 沸点：
  244.0±0.0 °C(Predicted)
• 密度：
  1.054±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温密封，干燥保存。

反应信息

• 作为反应物：
  描述：

  (S)-2-甲基-2-苯氧基甲醇 在 吡啶 、 sodium hydroxide 作用下， 以 乙醚 为溶剂， 反应 5.0h， 生成 (2''S)-2-<4'-(2''-phenoxypropyloxy)benzyl>cyclohexan-1-one
  参考文献：
  名称：

  2-（4-羟苄基）环己-1-酮系列的新型幼体

  摘要：

  合成并研究了一系列昆虫幼体激素类似物（类幼体）。这些类黄酮的基本骨架包含三个环和一个短的脂族亚基，并带有两个或三个手性中心（取决于适当的结构；请参见6–9）。位于1，2-二苯氧基丙烷亚单元中的手性中心具有（RS），（R）（a系列）或（S）（b系列）的构型。对少年类进行了生物筛选，并简要介绍了其初步结果。

  DOI：

  10.1002/hlca.19940770210
• 作为产物：
  描述：

  (S)-2-phenoxy-1-propyl acetate 在 lipase from Pseudomonas Cepacia 、 phosphate buffer pH 7.0 作用下， 生成 (S)-2-甲基-2-苯氧基甲醇
  参考文献：
  名称：

  Molecular Basis for Enantioselectivity of Lipase from Pseudomonas cepacia toward Primary Alcohols. Modeling, Kinetics, and Chemical Modification of Tyr29 to Increase or Decrease Enantioselectivity

  摘要：

  Lipase from Pseudomonas cepacia (PCL) shows good enantioselectivity toward primary alcohols, An empirical rule can predict which enantiomer of a primary alcohol reacts faster, but there is no reliable strategy to increase the enantioselectivity. We used a combination of molecular modeling of lipase-transition state analogue complexes and kinetic measurements to identify the molecular basis of the enantioselectivity toward two primary alcohols: 2-methyl-3-phenyl-1-propanol, 1, and 2-phenoxy-1-propanol, 2. In hydrolysis of the acetate esters, PCL favors the (S)-enantiomer of both substrates (E = 16 and 17, respectively), but, due to changes in priorities of the substituents, the (S)-enantiomers of 1 and 2 have opposite shapes. Computer modeling of transition state analogues bound to PCL show that primary alcohols bind to PCL differently than secondary alcohols. Modeling and kinetics suggest that the enantioselectivity of PCL toward 1 comes from the binding of the methyl group at the stereocenter within a hydrophobic pocket for the fast-reacting enantiomer, but not for the slow-reacting enantiomer. On the other hand, the enantioselectivity toward 2 comes from an extra hydrogen bond between the phenoxy oxygen of the substrate to the phenolic OH of Tyr29. This hydrogen bond may slow release of the (R)-alcohol and thus account for the reversal of enantioselectvity. To decrease the enantioselectivity of PCL toward 2-acetate by a factor of 2 to E = 8, we eliminated the hydrogen bond by acetylation of the tyrosyl residues with N-acetylimidazole. To increase the enantioselectivity of PCL toward 2-acetate by a factor of 2 to E = 36, we increased the strength of the hydrogen bond by nitration of the tyrosyl residues with tetranitromethane. This is one of the first examples of a rationally designed modification of a lipase to increase enantioselectivity.

  DOI：

  10.1021/jo981783y

文献信息

• CATALYSTS AND PROCESSES FOR THE HYDROGENATION OF AMIDES
  申请人：Bergens Steven

  公开号：US20140163225A1

  公开（公告）日：2014-06-12

  There is provided a process for the reduction of one or more amide moieties in a compound comprising contacting the compound with hydrogen gas and a transition metal catalyst in the presence or absence of a base under conditions for the reduction an amide bond. The presently described processes can be performed at low catalyst loading using relatively mild temperature and pressures, and optionally, in the presence or absence of a base or high catalyst loadings using low temperatures and pressures and high loadings of base to effect dynamic kinetic resolution of achiral amides.

  提供了一种过程，用于在存在或不存在碱的条件下，将化合物与氢气和过渡金属催化剂接触，以还原一个或多个酰胺基团。目前描述的这些过程可以在低催化剂负载下进行，使用相对温和的温度和压力，并且可以选择在存在或不存在碱或高催化剂负载下使用低温和低压以及高负载碱的条件下，实现不对映体酰胺的动态动力学分辨。
• Highly Enantioselective Hydrogenation of Amides via Dynamic Kinetic Resolution Under Low Pressure and Room Temperature
  作者：Loorthuraja Rasu、Jeremy M. John、Elanna Stephenson、Riley Endean、Suneth Kalapugama、Roxanne Clément、Steven H. Bergens

  DOI：10.1021/jacs.6b12254

  日期：2017.3.1

  High-throughput screening and lab-scale optimization were combined to develop the catalytic system trans-RuCl2((S,S)-skewphos)((R,R)-dpen), 2-PrONa, and 2-PrOH. This system hydrogenates functionalized α-phenoxy and related amides at room temperature under 4 atm H2 pressure to give chiral alcohols with up to 99% yield and in greater than 99% enantiomeric excess via dynamic kinetic resolution.

  高通量筛选和实验室规模优化相结合，开发了催化系统 trans-RuCl2((S,S)-skewphos)((R,R)-dpen)、2-PrONa 和 2-PrOH。该系统在室温和 4 个大气压的 H2 压力下氢化功能化的 α-苯氧基和相关酰胺，通过动态动力学拆分以高达 99% 的产率和大于 99% 的对映体过量得到手性醇。
• Homobenzotetramisole-Catalyzed Kinetic Resolution of α-Aryl-, α-Aryloxy-, and α-Arylthioalkanoic Acids
  作者：Xing Yang、Vladimir B. Birman

  DOI：10.1002/adsc.200900451

  日期：2009.10

  Effective kinetic resolution of alpha-aryl-, alpha-aryloxy-, and alpha-arylthioalkanoic acids has been achieved via in situ generation of their symmetrical anhydrides and enantioselective alcoholysis in the presence of homobenzotetramisole (HBTM) 3.

  α-芳基-、α-芳氧基-和α-芳基硫代链烷酸的有效动力学拆分是通过它们的对称酸酐的原位生成和在高苯并四咪唑 (HBTM) 3 存在下的对映选择性醇解实现的。
• Picolinamide compounds with fungicidal activity
  申请人：DOW AGROSCIENCES LLC

  公开号：US10188109B2

  公开（公告）日：2019-01-29

  This disclosure relates to picolinamides of Formula I and their use as fungicides.

  本公开涉及式 I 的吡啶酰胺及其作为杀菌剂的用途。
• [EN] PYRIDIN-3-YL ACETIC ACID DERIVATIVES AS INHIBITORS OF HUMAN IMMUNODEFICIENCY VIRUS REPLICATION<br/>[FR] DÉRIVÉS D'ACIDE PYRIDIN-3-YL-ACÉTIQUE EN TANT QU'INHIBITEURS DE LA RÉPLICATION DU VIRUS DE L'IMMUNODÉFICIENCE HUMAINE
  申请人：VIIV HEALTHCARE UK NO 5 LTD

  公开号：WO2019244066A3

  公开（公告）日：2020-03-05