(S)-3-(4-methoxyphenyl)butan-2-one | 27883-07-4

• 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)-3-(4-methoxyphenyl)butan-2-one
• 英文别名: (3S)-3-(4-methoxyphenyl)butan-2-one
• CAS: 27883-07-4
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: OWMXLURRBPTXHT-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-[(S)-1-(4-Methoxy-phenyl)-ethyl]-2,5,5-trimethyl-[1,3]dioxane 在 盐酸 作用下， 以 丙酮 为溶剂， 生成 (S)-3-(4-methoxyphenyl)butan-2-one
  参考文献：
  名称：

  通过使用有机铝试剂进行替代型 1,2-重排。手性α-芳基（或烯基）酮缩醛的合成

  摘要：

  通过使用有机铝试剂引入烷基或炔基，通过芳基（或烯基）的新型立体定向 1,2-重排合成标题化合物。

  DOI：

  10.1246/cl.1986.277

文献信息

• Catalytic Enantioselective Protoboration of Disubstituted Allenes. Access to Alkenylboron Compounds in High Enantiomeric Purity
  作者：Hwanjong Jang、Byunghyuck Jung、Amir H. Hoveyda

  DOI：10.1021/ol5022417

  日期：2014.9.5

  Proto-boryl additions to 1,1-disubstituted allenes in the presence of 1.0–5.0 mol % of chiral NHC–Cu complexes, B2(pin)2, and t-BuOH proceed to afford alkenyl–B(pin) products in up to 98% yield, >98:2 site selectivity, and 98:2 er. The enantiomerically enriched alkenylboron products can be converted to otherwise difficult-to-access alkenyl bromides, methyl ketones or carboxylic acids. What’s more,

  在 1.0–5.0 mol% 的手性 NHC-Cu 配合物、B 2 (pin) 2和t- BuOH存在下，原硼基加成到 1,1-二取代的丙二烯上，得到烯基-B(pin) 产物高达 98% 的产率、>98:2 的位点选择性和 98:2 er。富含对映异构体的烯基硼产物可以转化为其他难以获得的烯基溴化物、甲基酮或羧酸。此外，相应的硼酸可用于高度立体选择性的 NHC-Cu 催化的烯丙基取代反应。
• Selective Baeyer–Villiger oxidation of racemic ketones in aqueous–organic media catalyzed by phenylacetone monooxygenase
  作者：Cristina Rodríguez、Gonzalo de Gonzalo、Daniel E. Torres Pazmiño、Marco W. Fraaije、Vicente Gotor

  DOI：10.1016/j.tetasy.2007.12.008

  日期：2008.2

  enantioselective kinetic resolution of a set of racemic substituted 3-phenylbutan-2-ones employing phenylacetone monooxygenase (PAMO) in non-conventional media was performed. The studies have revealed the effects of a range of solvents on the biocatalytic properties of the biocatalyst. Also, the enzymatic oxidation of α-acetylphenylacetonitrile was performed using organic cosolvents. This has resulted in a dynamic

  使用苯丙酮单加氧酶（PAMO）在非常规介质中进行了一组外消旋取代的3-苯基丁烷-2-酮的对映选择性动力学拆分。研究已经揭示了多种溶剂对生物催化剂的生物催化性能的影响。另外，使用有机助溶剂进行α-乙酰基苯基乙腈的酶促氧化。这导致该氰酮的动态动力学拆分，产生对映纯（R）-2-乙酰氧基苯基乙腈，其产率取决于所采用的反应条件。
• Enantioselective Sequential Catalytic Arylation‐Fukuyama Cross‐coupling of 1,1‐Biszincioalkane Linchpins
  作者：Federico Banchini、Baptiste Leroux、Erwan Le Gall、Marc Presset、Olivier Jackowski、Fabrice Chemla、Alejandro Perez‐Luna

  DOI：10.1002/chem.202301084

  日期：2023.6.27

  1,1‐Bis(iodozincio)alkanes are used as dinucleophilic linchpins in an enantioselective double cross‐coupling reaction sequence involving aryl iodides and then thioesters. The two catalytic C−C bond‐forming reactions are achieved in the same pot through two distinct palladium‐based catalytic systems: a first non‐enantioselective one delivering configurationally labile secondary benzylzinc species from an achiral precursor, and a second enantioconvergent one that operates a highly efficient dynamic kinetic resolution of the racemic intermediates. This strategy, new in the area of asymmetric synthesis through two consecutive electrophilic substitution reactions of geminated C(sp³)‐organodimetallics, provides useful methodology to access in a modular fashion acyclic α‐disubstituted ketone products with very high enantiomeric purity.

  摘要 1,1-双（碘代锌）烷烃在涉及芳基碘化物和硫代酯的对映体选择性双交叉偶联反应序列中用作二亲核键。这两个催化 C-C 键形成反应是通过两个不同的钯基催化系统在同一锅中实现的：第一个非对映体选择性催化系统从非对映体前体中提供构型易变的仲苄基锌物种，第二个对映体转换催化系统对外消旋中间体进行高效的动态动力学解析。这种策略是通过两个连续的亲电取代反应进行宝石化 C（sp3）-有机二金属的不对称合成领域的新方法，为以模块化方式获得对映体纯度极高的α-二取代酮产品提供了有用的方法。
• Baeyer–Villiger monooxygenase-catalyzed kinetic resolution of racemic α-alkyl benzyl ketones: enzymatic synthesis of α-alkyl benzylketones and α-alkyl benzylesters
  作者：Cristina Rodríguez、Gonzalo de Gonzalo、Daniel E. Torres Pazmiño、Marco W. Fraaije、Vicente Gotor

  DOI：10.1016/j.tetasy.2009.03.018

  日期：2009.6

  The application of three BVMOs for the enantioselective oxidation of 3-phenylbutan-2-ones with different substituents in the aromatic moiety is described. By choosing the appropriate biocatalyst and substrate combination, chiral ketones and esters can be obtained with excellent enantiopurities. This methodology could also be applied to the resolution of racemic alpha-alkyl benzylketones with longer alkyl chains as well as with two substituted alpha-substituted benzylacetones. A kinetic analysis revealed that the BVMOs studied effectively convert all tested compounds showing that the enzymes are tolerant towards the substrate structure while being highly enantioselective. These properties render BVMOs as valuable biocatalysts for the preparation of compounds with high interest in organic synthesis. (C) 2009 Elsevier Ltd. All rights reserved.
• SUBSTITUTION-TYPE 1,2-REARRANGEMENT BY USING ORGANOALUMINUM REAGENTS. SYNTHESIS OF CHIRAL α-ARYL(OR ALKENYL)KETONE ACETALS
  作者：Yutaka Honda、Eitaro Morita、Gen-ichi Tsuchihashi

  DOI：10.1246/cl.1986.277

  日期：1986.3.5

  Title compounds were synthesized via novel stereospecific 1,2-rearrangement of an aryl (or alkenyl) group accompanied by introduction of an alkyl or alkynyl group by using organoaluminum reagents.

  通过使用有机铝试剂引入烷基或炔基，通过芳基（或烯基）的新型立体定向 1,2-重排合成标题化合物。