(2E)-3-(4-fluorophenyl)-2-nitroprop-2-en-1-ol

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (2E)-3-(4-fluorophenyl)-2-nitroprop-2-en-1-ol
• 英文别名: (E)-3-(4-fluorophenyl)-2-nitroprop-2-en-1-ol
• 化学式: C₉H₈FNO₃
• 分子量: 197.166
• InChiKey: GSPOXHKPFNGIRW-WEVVVXLNSA-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：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2E)-3-(4-fluorophenyl)-2-nitroprop-2-en-1-ol 在 三乙胺 、 奎尼丁 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 生成 (3S,4R)-4-(4-fluorophenyl)-3-nitro-6-phenyl-2,3,4,6-tetrahydro-5H-pyrano[3,2-c]quinolin-5-one
  参考文献：
  名称：

  Asymmetric synthesis of tetrahydropyran[3,2-c]quinolinones via an organocatalyzed formal [3 + 3] annulation of quinolinones and MBH 2-naphthoates of nitroolefin

  摘要：

  An efficient asymmetric and enantio-swithchable organocatalytic [3 + 3] annulation reaction using MBH-2-naphthoates of nitroalkenes and 4-hydroxyquinolin-2(1H)-ones has been developed. Densely substituted tetrahydropyrano[3,2-c]quinolinones scaffolds with two adjacent stereogenic centers are obtained with high yield (up to 95% yield) and good stereoselectivities (up to >20:1 dr and 96% ee) in an enantio-switchable manner. Furthermore, gram scale synthesis was achieved and the nitro group could easily transform into an amino group without any appreciable loss in the diastereo- and enantioselectivity. (C) 2019 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2019.08.040
• 作为产物：
  描述：

  对氟苯甲醛 在 咪唑 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 (2E)-3-(4-fluorophenyl)-2-nitroprop-2-en-1-ol
  参考文献：
  名称：

  Asymmetric synthesis of tetrahydropyran[3,2-c]quinolinones via an organocatalyzed formal [3 + 3] annulation of quinolinones and MBH 2-naphthoates of nitroolefin

  摘要：

  An efficient asymmetric and enantio-swithchable organocatalytic [3 + 3] annulation reaction using MBH-2-naphthoates of nitroalkenes and 4-hydroxyquinolin-2(1H)-ones has been developed. Densely substituted tetrahydropyrano[3,2-c]quinolinones scaffolds with two adjacent stereogenic centers are obtained with high yield (up to 95% yield) and good stereoselectivities (up to >20:1 dr and 96% ee) in an enantio-switchable manner. Furthermore, gram scale synthesis was achieved and the nitro group could easily transform into an amino group without any appreciable loss in the diastereo- and enantioselectivity. (C) 2019 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cclet.2019.08.040

文献信息

• Biocatalytic enantioselective approach to 3-aryl-2-nitropropanols: Synthesis of enantioenriched (R)-5-methoxy-3-aminochroman, a key precursor to the antidepressant drug Robalzotan
  作者：Claudio Fuganti、Alessandro Sacchetti

  DOI：10.1016/j.molcatb.2010.06.003

  日期：2010.10

  results of our studies on the biocatalytic enantioselective synthesis of different 3-aryl-2-nitropropanols are presented. These compounds could be obtained in moderate to good ee both by baker's yeast mediated reduction of (E)-2-nitro-3-arylprop-2-en-1-ol precursors and by lipase kinetic resolution of racemic 3-aryl-2-nitropropanols. The synthesis of enantioenriched (R)-5-methoxy-3-aminochroman is also

  提出了我们对不同的3-芳基-2-硝基丙醇的生物催化对映选择性合成的研究结果。这些化合物可以通过面包酵母的介导的（E）-2-硝基-3-芳基丙-2-烯-1-醇前体还原和脂肪酶动力学拆分外消旋3-芳基-2-烯而以中等至良好的ee值获得。硝基丙醇。还实现了对映体富集的（R）-5-甲氧基-3-氨基苯并二氢吡喃的合成。该重要部分存在于对中枢神经系统有活性的不同分子中，并且还是合成强效5-HT 1A拮抗剂Robalzotan（NAD299）的前体。
• 1,3-Dipolar Cycloaddition on Baylis-Hillman Adducts: Novel Synthesis of Pyrrolidines, Spiropyrrolidines, and Spiropyrrolizidines
  作者：Manickam Bakthadoss、Nagappan Sivakumar、Anthonisamy Devaraj、Duddu Sharada

  DOI：10.1055/s-0030-1260053

  日期：2011.7

  A facile regio- and stereoselective synthesis of functionalized pyrrolidines, spiropyrrolidines, and spiropyrrolizidines using the Baylis-Hillman adducts derived from nitroolefins via intermolecular [3+2]-cycloaddition reaction is reported. Baylis-Hillman reaction - intermolecular [3+2] cycloaddition - azomethine ylides - 1,3-dipolar cycloaddition - pyrrolidines - spiro compounds

  报道了使用衍生自硝基烯烃的Baylis-Hillman加合物通过分子间[3 + 2]-环加成反应的功能性吡咯烷，螺吡咯烷和螺吡咯并核苷的容易的区域和立体选择性合成。 Baylis-Hillman反应-分子间[3 + 2]环加成-偶氮甲亚胺-1,3-偶极环加成-吡咯烷-螺环化合物
• Domino reactions for the synthesis of various α-substituted nitro alkenes
  作者：Stefania Fioravanti、Lucio Pellacani、Maria Cecilia Vergari

  DOI：10.1039/c1ob06260c

  日期：——

  Efficient one-pot methods for the synthesis of variously functionalised conjugated nitro alkenes have been reported. Despite the utility in different fields of these compounds, only a few multi-step syntheses have been reported in the literature, giving the target compounds in low overall yields. α-Nitro acrylates or cinnamates, α-nitro α,β-unsaturated ketones and, most importantly, aromatic and heteroaromatic

  已经报道了用于合成各种官能化的共轭硝基烯烃的有效的一锅法。尽管这些化合物在不同领域有实用性，但文献中仅报道了几步合成，以较低的总收率得到了目标化合物。以高收率获得了α-硝基丙烯酸酯或肉桂酸酯，α-硝基α，β-不饱和酮，以及最重要的是芳香族和杂芳香族（E）-2-硝基烯丙醇，这些化合物具有众所周知的抗癌活性。通过多米诺骨牌缩合脱水过程获得高非对映异构体纯度。
• Organocatalytic desymmetrization of cyclic meso-anhydrides through enantioselective alcoholysis with functionalized primary nitroallylic alcohols
  作者：Yan ming Chen、Mamatha Amireddy、Kwunmin Chen

  DOI：10.1016/j.tet.2014.10.008

  日期：2014.11

  The direct organocatalytic desymmetrization of cyclic meso-anhydrides was achieved by alcoholysis with nitroallylic alcohols. The reaction between primary nitroallylic alcohols and cyclic meso-anhydrides catalyzed by cinchonidine derived thiourea organocatalyst II (10 mol %) proceeded smoothly. The corresponding hemiesters were obtained in high chemical yields with high to excellent levels of stereoselectivity

  环状内消旋酸酐的直接有机催化去对称化是通过用硝基烯丙醇进行醇解而实现的。由辛可尼定衍生的硫脲有机催化剂II（10 mol％）催化的伯硝基烯丙醇与环状内消旋酸酐的反应进行得很顺利。相应的半酯以高化学产率获得，具有高至极好的立体选择性水平（高达90％的收率和99％的ee）。另一方面，当氨基辛可尼定衍生物（III）在类似反应条件下用作有机催化剂时，观察到对映选择性的逆转。这证明了在环的去对称化中亲核组分的活化的例子。内消旋酸酐。
• 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