1-oxo-3-phenylpropan-2-yl 4-nitrobenzoate | 1262801-38-6

• 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: 1-oxo-3-phenylpropan-2-yl 4-nitrobenzoate
• 英文别名: (1-Oxo-3-phenylpropan-2-yl) 4-nitrobenzoate
• CAS: 1262801-38-6
• 化学式: C₁₆H₁₃NO₅
• 分子量: 299.283
• InChiKey: MLBFGFHNELNQJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  89.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  乙醇 、 1-oxo-3-phenylpropan-2-yl 4-nitrobenzoate 在 2-mesityl-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol-2-ium tetrafluoroborate 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以58%的产率得到3-苯丙酸乙酯
  参考文献：
  名称：

  α-Aroyloxyaldehydes: scope and limitations as alternatives to α-haloaldehydes for NHC-catalysed redox transformations

  摘要：

  α-芳氧醛是一种容易制备且在桌面上稳定的合成中间体。它们在NHC促进的氧化还原酯化反应以及[4+2]环加成反应中作为α-卤醛的替代物的能力得到了描述。

  DOI：

  10.1039/c0cc02456b
• 作为产物：
  描述：

  1-phenylbut-3-en-2-yl p-nitrobenzoate 在 臭氧 、 二甲基硫 作用下， 以 二氯甲烷 为溶剂， 以69%的产率得到1-oxo-3-phenylpropan-2-yl 4-nitrobenzoate
  参考文献：
  名称：

  α-Aroyloxyaldehydes: scope and limitations as alternatives to α-haloaldehydes for NHC-catalysed redox transformations

  摘要：

  α-芳氧醛是一种容易制备且在桌面上稳定的合成中间体。它们在NHC促进的氧化还原酯化反应以及[4+2]环加成反应中作为α-卤醛的替代物的能力得到了描述。

  DOI：

  10.1039/c0cc02456b

文献信息

• N-Heterocyclic Carbene-Catalyzed Chemoselective Monoacylation of 1,<i>n</i>-Linear Diols
  作者：Takahiro Soeta、Kota Kaneta、Yuichi Hatanaka、Tomonori Ida、Yutaka Ukaji

  DOI：10.1021/acs.orglett.1c02749

  日期：2021.11.5

  discusses the N-heterocyclic carbene (NHC)-catalyzed redox monoacylation of 1,n-linear diols using α-benzoyloxyaldehydes. The reactions afforded monoacylated diols in moderate to good selectivities and chemical yields. Our original NHC bearing a pyridine moiety plays an important role in achieving good chemoselectivities. A wide range of 1,n-linear diols were successfully applied to this reaction.

  本文讨论了使用 α-苯甲酰氧醛对 1, n-线性二醇进行N-杂环卡宾 (NHC) 催化氧化还原单酰化反应。该反应以中等至良好的选择性和化学产率提供单酰化二醇。我们带有吡啶部分的原始 NHC 在实现良好的化学选择性方面发挥着重要作用。广泛的 1, n-线性二醇成功应用于该反应。
• Enantioselective NHC‐Catalyzed Redox [2+2] Cycloadditions with Perfluoroketones: A Route to Fluorinated Oxetanes
  作者：Alyn T. Davies、Alexandra M. Z. Slawin、Andrew D. Smith

  DOI：10.1002/chem.201504256

  日期：2015.12.21

  carbene (NHC) catalyzed redox formal [2+2] cycloaddition between α‐aroyloxyaldehydes and perfluoroketones, followed by ring‐opening in situ delivers a variety of perfluorinated β‐hydroxycarbonyl compounds in good yield, and excellent diastereo‐ and enantioselectivity. Through a reductive work‐up and subsequent cyclization, this protocol offers access to highly substituted fluorinated oxetanes in two

  N-杂环卡宾（NHC）催化α-芳酰氧基醛与全氟酮之间的氧化还原形式[2 + 2]环加成反应，然后原位开环提供各种全氟β-羟基羰基化合物，收率高，非对映和对映选择性优异。通过还原后处理和随后的环化，该方案可分两步以高ee值获得高度取代的氟化氧杂环丁烷。
• NHC-catalyzed enantioselective synthesis of β-trifluoromethyl-β-hydroxyamides
  作者：Alyn T Davies、Mark D Greenhalgh、Alexandra M Z Slawin、Andrew D Smith

  DOI：10.3762/bjoc.16.129

  日期：——

  The N-heterocyclic carbene (NHC)-catalyzed formal [2 + 2] cycloaddition between α-aroyloxyaldehydes and trifluoroacetophenones, followed by ring opening with an amine or a reducing agent is described. The resulting β-trifluoromethyl-β-hydroxyamide and alcohol products are produced with reasonable diastereocontrol (typically ≈70:30 dr) and excellent enantioselectivity, and they can be isolated in moderate

  描述了在α-芳酰氧基醛和三氟苯乙酮之间进行N-杂环卡宾（NHC）催化的甲醛[2 + 2]环加成反应，然后用胺或还原剂进行开环。生成的β-三氟甲基-β-羟基酰胺和醇产物具有合理的非对映异构控制（通常≈70:30 dr）和出色的对映选择性，可以作为单一非对映异构体以中等至良好的收率分离。
• Asymmetric NHC-Catalyzed Redox α-Amination of α-Aroyloxyaldehydes
  作者：James E. Taylor、David S. B. Daniels、Andrew D. Smith

  DOI：10.1021/ol402955f

  日期：2013.12.6

  (NHC)-catalyzed redox reaction of α-aroyloxyaldehydes with N-aryl-N-aroyldiazenes to form α-hydrazino esters with high enantioselectivity (up to 99% ee) is reported. The hydrazide products are readily converted into enantioenriched N-aryl amino esters through samarium(II) iodide mediated N–N bond cleavage.

  报道了通过 N-杂环卡宾 (NHC) 催化的 α-芳酰氧基醛与N-芳基-N-芳酰基二氮烯的氧化还原反应形成具有高对映选择性（高达 99% ee）的 α-肼基酯的不对称 α-胺化。通过碘化钐（II）介导的 N-N 键断裂，酰肼产物很容易转化为对映体富集的N-芳基氨基酯。
• Stereospecific Asymmetric N-Heterocyclic Carbene (NHC)-Catalyzed Redox Synthesis of Trifluoromethyl Dihydropyranones and Mechanistic Insights
  作者：Alyn T. Davies、James E. Taylor、James Douglas、Christopher J. Collett、Louis C. Morrill、Charlene Fallan、Alexandra M. Z. Slawin、Gwydion Churchill、Andrew D. Smith

  DOI：10.1021/jo401433q

  日期：2013.9.20

  N-Heterocyclic carbene (NHC)-catalyzed redox asymmetric hetero-Diels-Alder reactions of alpha-aroyloxyaldehydes with beta-trifluoromethyl enones generates synthetically useful dihydropyranones containing a stereogenic trifluoromethyl substituent in good yields (up to 81%) and excellent diastereoselectivity and enantioselectivity (up to >95:5 dr and >99% ee). The process is stereospecific, with use of either (E)- or (Z)-beta-trifluoromethyl enones forming syn- or anti-dihydropyranone products, respectively. Mechanistic studies through in situ kinetic analysis of the reaction reveal key differences in reactivity between chiral NHC precursor 1 and an achiral NHC precursor.