3-(3,4-dimethoxyphenyl)-2-nitroprop-2-en-1-ol | 718597-85-4

• 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: 3-(3,4-dimethoxyphenyl)-2-nitroprop-2-en-1-ol
• 英文别名: 3-(3,4-Dimethoxyphenyl)-2-nitroprop-2-en-1-ol
• CAS: 718597-85-4
• 化学式: C₁₁H₁₃NO₅
• 分子量: 239.228
• InChiKey: QPQHKVQVHRONRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  84.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(3,4-dimethoxyphenyl)-2-nitroprop-2-en-1-ol 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 反应 0.17h， 以80%的产率得到
  参考文献：
  名称：

  的高度多样化合成1,2,3-三唑衍生物通过多米诺[3 + 2]环加成的叠氮化物和脱硝反应序列†

  摘要：

  在本文中，已经描述了在无催化剂的条件下通过多米诺[3 + 2]叠氮化物环加成和脱硝反应的顺序优雅合成1,2,3-三唑衍生物的方法。在没有催化剂存在的情况下，用叠氮化钠处理硝基烯烃对Baylis-Hillman加合物及其环状衍生物的反应，可平稳地获得1,2,3-三唑衍生物。

  DOI：

  10.1039/c5ra14195h

文献信息

• Control of the Organocatalytic Enantioselective α-Alkylation of Vinylogous Carbonyl Enolates for the Synthesis of Tetrahydropyran Derivatives and Beyond
  作者：Pavan Sudheer Akula、Yung-Ju Wang、Bor-Cherng Hong、Gene-Hsiang Lee、Su-Ying Chien

  DOI：10.1021/acs.orglett.1c01426

  日期：2021.6.18

  The organocatalytic α-alkylation of vinylogous carbonyl compounds to hydroxynitroolefins for the synthesis of hemiacetals was realized with excellent enantioselectivities and in high yields. High diastereoselectivity (up to >20:1) has been accomplished with the addition of Et3N. The α- and γ-alkylation of vinylogous ketone against nitroolefins displayed high but opposite facial selectivities. Transformation

  以优异的对映选择性和高产率实现了用于合成半缩醛的乙烯基羰基化合物的有机催化 α-烷基化反应生成羟基硝基烯烃。通过添加 Et 3 N实现了高非对映选择性（高达 >20:1）。乙烯基酮对硝基烯烃的 α-和 γ-烷基化显示出高但相反的表面选择性。已证明半缩醛产物转化为其他多环化合物，包括euroticin B 类似物。
• Synthesis, Structure, and <i>E</i>−<i>Z</i> Isomerization of β-(Hetero)aryl-α-nitro-α,β-enals
  作者：Patricia Martínez-Bescos、Fernando Cagide-Fagín、Luis F. Roa、Juan Carlos Ortiz-Lara、Krzysztof Kierus、Lidia Ozores-Viturro、Marta Fernández-González、Ricardo Alonso

  DOI：10.1021/jo702731b

  日期：2008.5.1

  The first general methodology for the gram-scale preparation of previously overlooked beta-(hetero)aryl-alpha-nitro-alpha,beta-enals (3) is reported. Condensation of (hetero) aromatic aldehydes with 2-nitroethanol gave the E-isomers of uncommon beta-(hetero)aryl-alpha-hydroxymethyl-alpha,beta-unsatured-nitroalkenes (2), as determined by NOE and X-ray studies. alpha-Nitro-alpha,beta-enals 3 were subsequently obtained by hypervalent iodine oxidation of 2 as E-Z-mixtures in solid form. They showed varied stability and solvent-dependent thermal-promoted and photopromoted E-Z interconversion. Starting with furfural, experimental conditions were developed to prepare the corresponding nitroenal 3a enriched in either the E or the Z isomer: E-3a/Z-3a approximate to 90/10 and 20/80, respectively. In contrast with other structurally related compounds, nitroenals 3 have their (hetero)aryl-vinyl unit and their formyl and nitro groups all in a planar arrangement, both in solid form and in solution; accordingly, they are colored compounds with predicted high dipole moments. As deduced from solution-NMR and X-ray data, the C=C and the C=O double bonds in 3 are exclusively s-cis-oriented; this disposition corresponds in fact to the DFT-computed most stable conformer.