(S)-4-nitro-3-phenylbutan-2-one | 1374758-63-0

• 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)-4-nitro-3-phenylbutan-2-one
• 英文别名: (S)-1-nitro-2-phenylbutan-3-one；(3S)-4-nitro-3-phenylbutan-2-one
• CAS: 1374758-63-0
• 化学式: C₁₀H₁₁NO₃
• 分子量: 193.202
• InChiKey: OTGGWWZEOIWIHN-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (3S)-2-methyl-4-nitro-3-phenylbutanal 在 氧气 、 甲氧苯胺 作用下， 以 甲苯 为溶剂， 20.0~50.0 ℃ 、1.01 MPa 条件下， 反应 49.0h， 以76%的产率得到(S)-4-nitro-3-phenylbutan-2-one
  参考文献：
  名称：

  通过金属氧化免费简易Ç访问手性酮？O2对醛的C键裂解

  摘要：

  为金属提供引导：通过标题反应，可以在分子氧存在的情况下轻松地从手性α，α'-二取代醛中获得官能化的手性酮（请参见方案）。与c  C键裂解方法提供替代的或更好的相对于在合成的手性酮所用的典型的键形成战略的一个方法。

  DOI：

  10.1002/anie.201107473

文献信息

• Catalytic Asymmetric Intermolecular Stetter Reactions of Enolizable Aldehydes with Nitrostyrenes: Computational Study Provides Insight into the Success of the Catalyst
  作者：Daniel A. DiRocco、Elizabeth L. Noey、K. N. Houk、Tomislav Rovis

  DOI：10.1002/anie.201107597

  日期：2012.3.5

  triazolium salt precatalyst has been developed that efficiently promotes the asymmetric intermolecular Stetter reaction of enolizable aldehydes and nitrostyrenes (see scheme). Trans fluorination of the catalyst architecture results in unparalleled reactivity and enantioselectivity in the desired transformation. A DFT study provides evidence of an electrostatic interaction as the source of the increased

  氟有帮助：我们开发了一种氟化三唑盐预催化剂，可有效促进烯醇化醛和硝基苯乙烯的不对称分子间Stetter反应（参见方案）。催化剂结构的反式氟化在所需的转化中产生无与伦比的反应活性和对映选择性。 DFT 研究提供了静电相互作用作为对映体感应增加的来源的证据。
• [EN] METHOD OF PREPARING CHIRAL KETONES FROM ALDEHYDES<br/>[FR] PROCÉDÉ DE PRÉPARATION DE CÉTONES CHIRALES À PARTIR D'ALDÉHYDES
  申请人：UNIV NANYANG TECH

  公开号：WO2013095301A1

  公开（公告）日：2013-06-27

  Present invention relates to a method of preparing a chiral α- or β-substituted ketone from the corresponding β- or γ-substituted aldehyde, wherein the ketone has formula (I), (III) or (V), and the corresponding aldehyde has formula (II), (IV) or (VI), respectively, the method comprising reacting the aldehyde of formula (II), (IV) or (VI) in the presence of an amine, oxygen and an organic solvent, wherein the reaction is carried out in the absence of a metal-based catalyst or a metal-based oxidant, wherein: R is H, a substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C2-C15 alkenyl, substituted or unsubstituted C2-C15 alkynyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C3-C15 cycloalkenyl, substituted or unsubstituted C3-C15 heterocycloalkyl, substituted or unsubstituted C3-C15 heterocycloalkenyl, substituted or unsubstituted C6-C15 aryl, or substituted or unsubstituted C6-C15 heteroaryl; and R' is H, a substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C2-C15 alkenyl, substituted or unsubstituted C2-C15 alkynyl, substituted or unsubstituted C3-C15 cycloalkyl, substituted or unsubstituted C3-C15 cycloalkenyl, substituted or unsubstituted C3-C15 heterocycloalkyl, substituted or unsubstituted C3-C15 heterocycloalkenyl, substituted or unsubstituted C6-C15 aryl, or substituted or unsubstituted C6-C15 heteroaryl.

  本发明涉及一种从相应的β-或γ-取代醛制备手性α-或β-取代酮的方法，其中酮具有式(I)、(III)或(V)，相应的醛具有式(II)、(IV)或(VI)，该方法包括在胺、氧和有机溶剂存在下反应式(II)、(IV)或(VI)的醛，其中反应在无金属催化剂或金属氧化剂存在下进行，其中：R为H、取代或未取代的C1-C10烷基、取代或未取代的C2-C15烯基、取代或未取代的C2-C15炔基、取代或未取代的C3-C15环烷基、取代或未取代的C3-C15环烯基、取代或未取代的C3-C15杂环烷基、取代或未取代的C3-C15杂环烯基、取代或未取代的C6-C15芳基或取代或未取代的C6-C15杂芳基；R'为H、取代或未取代的C1-C10烷基、取代或未取代的C2-C15烯基、取代或未取代的C2-C15炔基、取代或未取代的C3-C15环烷基、取代或未取代的C3-C15环烯基、取代或未取代的C3-C15杂环烷基、取代或未取代的C3-C15杂环烯基、取代或未取代的C6-C15芳基或取代或未取代的C6-C15杂芳基。
• METHOD OF PREPARING CHIRAL KETONES FROM ALDEHYDES
  申请人：Nanyang Technological University

  公开号：US20140309459A1

  公开（公告）日：2014-10-16

  Present invention relates to a method of preparing a chiral α- or β-substituted ketone from the corresponding β- or γ-substituted aldehyde, wherein the ketone has formula (I), (III) or (V), and the corresponding aldehyde has formula (II), (IV) or (VI), respectively, the method comprising reacting the aldehyde of formula (II), (IV) or (VI) in the presence of an amine, oxygen and an organic solvent, wherein the reaction is carried out in the absence of a metal-based catalyst or a metal-based oxidant, wherein: R is H, a substituted or unsubstituted C 1 -C 10 alkyl, substituted or unsubstituted C 2 -C 15 alkenyl, substituted or unsubstituted C 2 -C 15 alkynyl, substituted or unsubstituted C 3 -C 15 cycloalkyl, substituted or unsubstituted C 3 -C 15 cycloalkenyl, substituted or unsubstituted C 3 -C 15 heterocycloalkyl, substituted or unsubstituted C 3 -C 15 heterocycloalkenyl, substituted or unsubstituted C 6 -C 15 aryl, or substituted or unsubstituted C 6 -C 15 heteroaryl; and R′ is H, a substituted or unsubstituted C 1 -C 10 alkyl, substituted or unsubstituted C 2 -C 15 alkenyl, substituted or unsubstituted C 2 -C 15 alkynyl, substituted or unsubstituted C 3 -C 15 cycloalkyl, substituted or unsubstituted C 3 -C 15 cycloalkenyl, substituted or unsubstituted C 3 -C 15 heterocycloalkyl, substituted or unsubstituted C 3 -C 15 heterocycloalkenyl, substituted or unsubstituted C 6 -C 15 aryl, or substituted or unsubstituted C 6 -C 15 heteroaryl.
• US9120721B2
  申请人：——

  公开号：US9120721B2

  公开（公告）日：2015-09-01
• Facile Access to Chiral Ketones through Metal-Free Oxidative CC Bond Cleavage of Aldehydes by O2
  作者：Bhoopendra Tiwari、Junmin Zhang、Yonggui Robin Chi

  DOI：10.1002/anie.201107473

  日期：2012.2.20

  the boot: The title reaction provides facile access to functionalized chiral ketones from chiral α,α′‐disubstituted aldehydes in the presence of molecular oxygen (see scheme). The CC bond‐cleavage approach offers an alternative or better method relative to the typical bond‐forming strategies used in synthesizing chiral ketones.

  为金属提供引导：通过标题反应，可以在分子氧存在的情况下轻松地从手性α，α'-二取代醛中获得官能化的手性酮（请参见方案）。与c  C键裂解方法提供替代的或更好的相对于在合成的手性酮所用的典型的键形成战略的一个方法。