(E)-3-(furan-3-yl)-2-nitroprop-2-en-1-ol | 915161-56-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: (E)-3-(furan-3-yl)-2-nitroprop-2-en-1-ol
• CAS: 915161-56-7
• 化学式: C₇H₇NO₄
• 分子量: 169.137
• InChiKey: CLJYVMBGDCIRCB-XVNBXDOJSA-N

物化性质

• 熔点：
  71-73 °C(Solv: dichloromethane (75-09-2); ligroine (8032-32-4))
• 沸点：
  339.2±37.0 °C(Predicted)
• 密度：
  1.371±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  79.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-3-(furan-3-yl)-2-nitroprop-2-en-1-ol 在 2-碘酰基苯甲酸 作用下， 以 乙酸乙酯 为溶剂， 生成 (Z)-3-(furan-3-yl)-2-nitroacrylaldehyde 、 (E)-3-(furan-3-yl)-2-nitroacrylaldehyde
  参考文献：
  名称：

  Synthesis, Structure, and E−Z Isomerization of β-(Hetero)aryl-α-nitro-α,β-enals

  摘要：

  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.

  DOI：

  10.1021/jo702731b
• 作为产物：
  描述：

  3-糠醛 、 2-硝基乙醇 在 氢氧化钾 、 盐酸 作用下， 以 水 为溶剂， 以91%的产率得到(E)-3-(furan-3-yl)-2-nitroprop-2-en-1-ol
  参考文献：
  名称：

  Synthesis, Structure, and E−Z Isomerization of β-(Hetero)aryl-α-nitro-α,β-enals

  摘要：

  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.

  DOI：

  10.1021/jo702731b

文献信息

• [EN] PROCESSES FOR THE PREPARATION OF PANCRATISTATIN AND PANCRATISTATIN ANALOGUES<br/>[FR] PROCÉDÉS DE PRÉPARATION DE PANCRATISTATINE ET D'ANALOGUES DE PANCRATISTATINE
  申请人：UNIV SANTIAGO COMPOSTELA

  公开号：WO2009026961A1

  公开（公告）日：2009-03-05

  Processes for the preparation of pancratistatin and pancratistatin analogues. The key step is the reaction of a 1,3-dioxan-5-one and a nitroolefine in the presence of an amine. The process may take place in an enantioselective way when a chiral amine is used. Reduction processes then give new and advanced intermediates that are useful for the preparation of pancratistatin or selected pancratistatin analogues. The reported process also provides a method for the efficient synthesis of nitroenals, starting materials of the synthesis. Analogues of pancratistatin are also provided.

  制备pancratistatin和pancratistatin类似物的过程。关键步骤是在胺的存在下，将1,3-二氧杂环戊酮和硝基烯烃进行反应。当使用手性胺时，该过程可能以对映选择性方式进行。然后，还可以通过还原过程得到新的和先进的中间体，这些中间体对于制备pancratistatin或选定的pancratistatin类似物非常有用。报告的过程还提供了一种高效合成硝基烯醛的方法，这是合成的起始材料。还提供了pancratistatin的类似物。
• Synthesis and evaluation of α-hydroxymethylated conjugated nitroalkenes for their anticancer activity: Inhibition of cell proliferation by targeting microtubules
  作者：Renu Mohan、Namrata Rastogi、Irishi N.N. Namboothiri、Shaikh M. Mobin、Dulal Panda

  DOI：10.1016/j.bmc.2006.07.035

  日期：2006.12

  (MBH) type reaction of a variety of aromatic and heteroaromatic conjugated nitroalkenes with formaldehyde in the presence of stoichiometric amounts of imidazole and catalytic amounts (10 mol %) of anthranilic acid at room temperature provided the corresponding hydroxymethylated derivatives in moderate to good yield. The parent nitroalkenes and their MBH adducts were subsequently screened for their anticancer

  在室温下，在化学计量的咪唑和催化量（10摩尔％）的邻氨基苯甲酸存在下，各种芳族和杂芳族共轭硝基烯烃与甲醛的Morita-Baylis-Hillman（MBH）型反应在室温下提供了相应的羟甲基化衍生物中等至良好的产量。随后筛选母体硝基烯烃及其MBH加合物的抗癌活性。发现一些MBH加合物在低微摩尔浓度下抑制子宫颈癌（HeLa）细胞增殖，最大抑制浓度在1-2 microM范围内。3-（（E）-2-硝基乙烯基）呋喃和三种有效的MBH加合物（3-（（E）-2-硝基乙烯基）噻吩，1-甲氧基-4-（（E））的羟甲基化衍生物的抗增殖活性-2-硝基乙烯基）苯和1，2-二甲氧基-4-（（E）-2-硝基乙烯基）苯与其抗微管活性很好地相关。在其有效浓度范围内，被测化合物扰动了有丝分裂纺锤体微管和染色体的组织。在羟甲基化硝基烯烃的存在下，异常的双极或多极有丝分裂纺锤体很明显。发现相间微管在相对较高浓度的测试化合物下
• α-Hydroxymethylation of conjugated nitroalkenes via the Morita–Baylis–Hillman reaction
  作者：Namrata Rastogi、Irishi N.N. Namboothiri、Miriam Cojocaru

  DOI：10.1016/j.tetlet.2004.04.069

  日期：2004.6

  The Morita–Baylis–Hillman reaction (MBHR) of conjugated nitroalkenes has been successfully carried out for the first time. A variety of aromatic and heteroaromatic nitroalkenes react with formaldehyde at room temperature in the presence of stoichiometric amounts of imidazole and catalytic amounts of anthranilic acid in THF providing moderate to good yields of the multifunctional adducts in most of

  共轭硝基烯烃的Morita-Baylis-Hillman反应（MBHR）首次成功进行。在大多数情况下，在化学计量的咪唑和催化量的邻氨基苯甲酸在THF中存在下，各种芳族和杂芳族硝基烯烃与甲醛在室温下反应。
• 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.