ethyl (E)-3-{4-methyl-2-[(E)-2-nitrovinyl]-phenoxy}prop-2-enoate | 1206883-96-6

• 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: ethyl (E)-3-{4-methyl-2-[(E)-2-nitrovinyl]-phenoxy}prop-2-enoate
• 英文别名: (E)-ethyl 3-(4-methyl-2-((E)-2-nitrovinyl)phenoxy)acrylate；ethyl (E)-3-[4-methyl-2-[(E)-2-nitroethenyl]phenoxy]prop-2-enoate
• CAS: 1206883-96-6
• 化学式: C₁₄H₁₅NO₅
• 分子量: 277.277
• InChiKey: GKOYVNLEJWAELH-CDJQDVQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl (E)-3-{4-methyl-2-[(E)-2-nitrovinyl]-phenoxy}prop-2-enoate 、 (benzoylmethylene)dimethylsulfurane 以 氯仿 为溶剂， 以99%的产率得到ethyl 8-methyl-1-(phenylcarbonyl)-4,4a,9b,9c-tetrahydro-1H-2,3,5-trioxa-2a-azapentaleno[1,6-ab]naphthalene-4-carboxylate
  参考文献：
  名称：

  硫叶立德和硝基烯烃的正式[4 + 1] / [3 + 2]环加成级联反应构建稠合杂环体系

  摘要：

  在控制之下：已开发出由硫代烷基化物和链烯键合的硝基烯烃形成的正式的[4 + 1] / [3 + 2]环加成级联反应，可有效合成稠合的多环杂环化合物，并具有良好的非对映异构控制性（优异的总收率）（参见方案）。还已经公开了该反应的催化不对称变体。

  DOI：

  10.1002/anie.200904766
• 作为产物：
  描述：

  ethyl (E)-3-(2-formyl-4-methylphenoxy)acrylate 在 potassium tert-butylate 、 甲基磺酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 叔丁醇 为溶剂， 反应 17.0h， 生成 ethyl (E)-3-{4-methyl-2-[(E)-2-nitrovinyl]-phenoxy}prop-2-enoate
  参考文献：
  名称：

  Synthesis of Highly Functionalized Chiral Benzopyrano[3,4-c]pyrrolidines Bearing Five Contiguous Stereogenic Centers

  摘要：

  A chiral bis(imidazolidine)pyridine-Cu complex smoothly catalyzed the asymmetric [3+2] cycloaddition reaction of alpha, beta-unsaturated ester-containing nitroalkenes with imino esters to give endo-pyrrolidine products in a highly enantioselective manner while maintaining the alpha, beta-unsaturated ester functionality. Subsequent intramolecular diastereoselective cyclizations of the obtained pyrrolidine products were accomplished by treatment with KF/Al2O3 in toluene/EtOH (4:1) to give highly functionalized benzopyrano[3,4-c]pyrrolidines bearing five contiguous stereogenic centers.

  DOI：

  10.1021/acs.joc.5b01445

文献信息

• Construction of Fused Heterocyclic Architectures by Formal [4+1]/[3+2] Cycloaddition Cascade of Sulfur Ylides and Nitroolefins
  作者：Liang-Qiu Lu、Fang Li、Jing An、Ji-Ji Zhang、Xiao-Lei An、Qiu-Lin Hua、Wen-Jing Xiao

  DOI：10.1002/anie.200904766

  日期：2009.12.7

  Under control: A formal [4+1]/[3+2] cycloaddition cascade of sulfur ylides and alkene‐tethered nitroolefins has been developed, and provides an efficient synthesis of fused polycyclic heterocyclic compounds in good to excellent overall yields with excellent diastereocontrol (see scheme). A catalytic asymmetric variant of this reaction has also been disclosed.

  在控制之下：已开发出由硫代烷基化物和链烯键合的硝基烯烃形成的正式的[4 + 1] / [3 + 2]环加成级联反应，可有效合成稠合的多环杂环化合物，并具有良好的非对映异构控制性（优异的总收率）（参见方案）。还已经公开了该反应的催化不对称变体。
• Synthesis of Highly Functionalized Chiral Benzopyrano[3,4-<i>c</i>]pyrrolidines Bearing Five Contiguous Stereogenic Centers
  作者：Toru Sato、Tomoya Miyazaki、Takayoshi Arai

  DOI：10.1021/acs.joc.5b01445

  日期：2015.10.16

  A chiral bis(imidazolidine)pyridine-Cu complex smoothly catalyzed the asymmetric [3+2] cycloaddition reaction of alpha, beta-unsaturated ester-containing nitroalkenes with imino esters to give endo-pyrrolidine products in a highly enantioselective manner while maintaining the alpha, beta-unsaturated ester functionality. Subsequent intramolecular diastereoselective cyclizations of the obtained pyrrolidine products were accomplished by treatment with KF/Al2O3 in toluene/EtOH (4:1) to give highly functionalized benzopyrano[3,4-c]pyrrolidines bearing five contiguous stereogenic centers.