(R)-2-(4-methoxyphenyl)propan-1-ol | 143590-14-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (R)-2-(4-methoxyphenyl)propan-1-ol
• 英文别名: 2-(4-methoxyphenyl)propan-1-ol；(2R)-2-methyl-2-(4-methoxy)phenyl-ethanol；(2R)-2-(4-methoxyphenyl)propan-1-ol
• CAS: 143590-14-1
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: VIPNDDUFWVYIPH-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 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：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-2-(4-methoxyphenyl)propan-1-ol 在 吡啶 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 生成 (S)-3-(4-methoxyphenyl)butanenitrile
  参考文献：
  名称：

  Total synthesis of sporochnols, fish deterrents from a marine alga

  摘要：

  Sporochnols, fish deterrents from a marine alga. were synthesized. using intramolecular C H insertion of alkylidenecarbene as a key step to construct the chiral quaternary center. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00857-2
• 作为产物：
  描述：

  [(2R)-2-(4-methoxyphenyl)propyl] acetate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (R)-2-(4-methoxyphenyl)propan-1-ol
  参考文献：
  名称：

  Enzyme catalyzed monohydrolysis of 2-aryl-1 3-propanediol diacetates. A study of structural effects of the aryl moiety on the enantioselectivity

  摘要：

  DOI：

  10.1016/s0040-4020(01)87892-3

文献信息

• Chiral α-Substituted Carbonyls and Alcohols from the S_N2‘ Displacement of Cuprates on Chiral Carbonates:  An Alternative to the Alkylation of Chiral Enolates
  作者：Claude Spino、Christian Beaulieu、Julie Lafrenière

  DOI：10.1021/jo000810t

  日期：2000.10.1

  A highly stereoselective sequence of reactions, based on the anti-selective S(N)2' addition of cuprates to allylic carbonates, transforms alkynes or alkenyl halides into carbonyls having alpha-chiral centers. The method, which uses menthone as a chiral auxiliary, is a useful alternative to the alkylation of chiral enolates with the added advantage of allowing for the "alkylation" of sec- and tert-alkyl

  基于铜酸盐向烯丙基碳酸酯的抗选择性S（N）2'加成，高度立体选择性的反应序列将炔烃或烯基卤化物转化为具有α-手性中心的羰基。该方法使用薄荷酮作为手性助剂，是手性烯醇盐烷基化的一种有用的替代方法，具有允许仲烷基和叔烷基和芳基“烷基化”的额外优点。
• Highly Enantioselective Catalytic Kinetic Resolution of α‐Branched Aldehydes through Formal Cycloaddition with Homophthalic Anhydrides
  作者：Umar Farid、Maria Luisa Aiello、Stephen J. Connon

  DOI：10.1002/chem.201902422

  日期：2019.8

  A new catalytic methodology was developed to promote an efficient one‐pot kinetic resolution of racemic aldehydes with selectivity (s*) of up to 91 (99:1 d.r., >99 % ee) in a cycloaddition reaction with enolizable anhydrides to afford dihydroisocoumarin products (a core prevalent in natural products and molecules of medicinal interest) containing three contiguous stereocentres.

  开发了一种新的催化方法，以促进外消旋醛的有效单锅动力学拆分，其选择性（s *）高达91（99：1 dr，> 99％  ee），可与可烯醇化的酸酐进行环加成反应，制得二氢异香豆素产品（在天然产物和药用分子中普遍存在的核心）包含三个连续的立体中心。
• Easily Accessible TADDOL-Derived Bisphosphonite Ligands: Synthesis and Application in the Asymmetric Hydroformylation of Vinylarenes
  作者：Simon Allmendinger、Hirotaka Kinuta、Bernhard Breit

  DOI：10.1002/adsc.201400657

  日期：2015.1.12

  The synthesis of chiral bidentate bisphosphonite ligands based on the TADDOL motif from readily available starting materials has been developed. Taking advantage of the modular nature of the building blocks, a diverse ligand library has been prepared. Their catalytic potential has been evaluated in the asymmetric hydroformylation of styrene and derivatives. These catalysts showed high activity and

  已经开发了从容易获得的起始原料合成基于TADDOL基序的手性双齿双膦酸酯配体。利用构建模块的模块化性质，已准备了一个多样化的配体库。在苯乙烯及其衍生物的不对称加氢甲酰化反应中，已对它们的催化潜力进行了评估。这些催化剂显示出高活性，并提供了高对映体纯度的醛。
• Highly regio- and enantioselective catalytic asymmetric hydroboration of α-substituted styrenyl derivatives
  作者：Clément Mazet、David Gérard

  DOI：10.1039/c0cc01547d

  日期：——

  The catalytic asymmetric hydroboration of a variety of 1,1-disubstituted olefins has been achieved with excellent yields, perfect regioselectivity and in some cases, high levels of enantioselectivity using readily accessible iridium catalyst.

  使用容易获得的铱催化剂，已经以优异的收率，完美的区域选择性以及在某些情况下高水平的对映选择性实现了各种1,1-二取代烯烃的催化不对称硼氢化反应。
• Enzyme‐Catalyzed Meinwald Rearrangement with an Unusual Regioselective and Stereospecific 1,2‐Methyl Shift
  作者：Ruipu Xin、Willy W. L. See、Hui Yun、Xirui Li、Zhi Li

  DOI：10.1002/anie.202204889

  日期：2022.7.11

  A highly regioselective and stereospecific enzyme-catalyzed Meinwald rearrangement of internal and cyclic epoxides through a 1,2-methyl shift gave aldehydes or ketones as the sole product with enantio-retention. The unique isomerization was incorporated into enantioselective cascades, providing novel access to chiral alcohols, acids and amines from readily available trans-β-methylstyrenes.

  高度区域选择性和立体特异性酶催化的内部和环状环氧化物通过 1,2-甲基移位的 Meinwald 重排产生醛或酮作为具有对映保留的唯一产物。独特的异构化被整合到对映选择性级联中，提供了从容易获得的反式-β-甲基苯乙烯中获得手性醇、酸和胺的新途径。