trans-1-hydroxymethyl-2-(2-methoxyphenyl)-1-nitroethylene | 1255037-07-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: trans-1-hydroxymethyl-2-(2-methoxyphenyl)-1-nitroethylene
• 英文别名: (E)-3-(2-methoxyphenyl)-2-nitroprop-2-en-1-ol
• CAS: 1255037-07-0
• 化学式: C₁₀H₁₁NO₄
• 分子量: 209.202
• InChiKey: HKVIEQZAEXCZAK-RMKNXTFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  75.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  trans-1-hydroxymethyl-2-(2-methoxyphenyl)-1-nitroethylene 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)-6-benzyl-9-(tert-butyl)-4-(2-methoxyphenyl)-3-nitro-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：

  邻甲氧基苯甲醛 在 咪唑 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 生成 trans-1-hydroxymethyl-2-(2-methoxyphenyl)-1-nitroethylene
  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
• First Friedel-Crafts Reaction of the Baylis-Hillman Adducts Derived from Nitroolefins: Application towards Synthesis of Pyrrolidines and Spiropyrrolidines
  作者：Manickam Bakthadoss、Nagappan Sivakumar

  DOI：10.1055/s-0030-1260557

  日期：2011.6

  A general and simple protocol for the arylation of ­Baylis-Hillman adducts derived from nitroolefins leading to novel classes of (E)-2-nitro-1,3-diarylprop-1-enes and 1-[(E)-2-nitro-3-arylallyl]naphthalenes via an intermolecular Friedel-Crafts reaction have been achieved. Further application of these compounds has been demonstrated for the synthesis of pyrrolidines and 3-spiropyrrolidines which are integral components of many natural products and bioactive molecules.

  通过分子间弗里德尔-卡夫斯反应，实现了从硝基烯烃衍生出的 Baylis-Hillman 加合物的芳基化的一般和简单方案，从而得到了新型 (E)-2-nitro-1,3-diarylprop-1-enes 和 1-[(E)-2-nitro-3-芳基烯丙基]萘。这些化合物在合成吡咯烷和 3-巯基吡咯烷方面的进一步应用已得到证实，而吡咯烷和 3-巯基吡咯烷是许多天然产品和生物活性分子的组成部分。
• A remarkable solvent effect on the reaction of 4-hydroxycoumarin with (E)-3-aryl-2-nitroprop-2-enol: Facile synthesis of highly substituted furo/pyrano[3,2-c]chromenes
  作者：Shivendra Singh、Anvita Srivastava、Shaikh M. Mobin、Sampak Samanta

  DOI：10.1039/c4ra10610e

  日期：——

  A remarkable solvent effect on the reaction of 4-hydroxycoumarin derivatives with (E)-3-aryl/hetero-aryl-2-nitroprop-2-enols has been observed in water and DMSO media. This result was employed for the straightforward syntheses of new functionalized furo/pyrano[3,2-c]chromenes in 63–93% yields and diasteromeric ratio up to ≤99 : 1. Moreover, a simple, mild, efficient and catalyst-free one-pot method

  在水和DMSO介质中，已观察到对4-羟基香豆素衍生物与（E）-3-芳基/杂芳基-2-硝基丙-2-烯醇的反应具有显着的溶剂作用。该结果用于新型官能化的呋喃/吡喃并[3,2- c ]色烯的直接合成，产率为63-93％，非对映异构体比例最高为≤99：1。此外，该方法简单，温和，高效且无催化剂一锅法可能会为香豆素核上的呋喃/吡喃环的成环提供另一种合成策略。此外，水对该反应的速率和选择性（产物）显示出显着的积极作用。
• First Synthesis of Bromo and Chloro Derivatives of Baylis-Hillman Adducts Derived from Nitroolefins: Application towards the Synthesis of a Dendrimer Core
  作者：Manickam Bakthadoss、Nagappan Sivakumar、Anthonisamy Devaraj

  DOI：10.1055/s-0030-1258409

  日期：2011.2

  For the first time Baylis-Hillman adducts derived from nitroolefins have been conveniently transformed into a novel class of building blocks, 1-[(E)-3-bromo-2-nitroprop-1-enyl]arenes and 1-[(E)-3-chloro-2-nitroprop-1-enyl]arenes, in very good yields via an SN2 reaction using simple reaction conditions. Further application of these compounds has been demonstrated for the synthesis of tris[(E)-2-nitr

  首次将衍生自​​硝基烯烃的Baylis-Hillman加合物首次方便地转化为一类新型的结构单元，即1-[（E）-3-溴-2-硝基-2-硝基丙-1-烯基]芳烃和1-[（E）通过使用简单的反应条件的S N 2反应，以非常好的收率得到-3-氯-2-硝基丙-1-基]芳烃。这些化合物的进一步应用已经证明可以合成三[（E）-2-硝基-3-芳基烯丙基]胺作为树枝状聚合物核。 Baylis-Hillman反应-乙酸铵-硝基烯烃-氯化铁（III）-氢溴酸