(3E)-3-benzylidene-5-nitroheptan-2-one | 874149-65-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (3E)-3-benzylidene-5-nitroheptan-2-one
• CAS: 874149-65-2
• 化学式: C₁₄H₁₇NO₃
• 分子量: 247.294
• InChiKey: XFLRROVYMSUTFU-UKTHLTGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3E)-3-benzylidene-5-nitroheptan-2-one 在 四丁基氟化铵 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 29.0h， 生成 (7E)-7-benzylidene-5-ethyl-8-methyl-5-nitro-3,4,4a,6-tetrahydro-2H-naphthalen-1-one
  参考文献：
  名称：

  Regioselective synthesis of pentasubstituted benzene derivatives: TBAF as an effective catalyst for the sequential Michael addition-intramolecular aldolization

  摘要：

  Polysubstituted benzene derivatives were synthesized starting from the Baylis-Hillman adducts via the sequential introduction of primary nitroalkane at the primary position, Michael addition to beta-branched Michael acceptor, aldol condensation, elimination of nitrous acid, and the final aromatization process. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.06.180
• 作为产物：
  描述：

  硝基丙烷 、 4-acetoxy-3-methylene-4-phenylbutan-2-one 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (3E)-3-benzylidene-5-nitroheptan-2-one
  参考文献：
  名称：

  Regioselective synthesis of pentasubstituted benzene derivatives: TBAF as an effective catalyst for the sequential Michael addition-intramolecular aldolization

  摘要：

  Polysubstituted benzene derivatives were synthesized starting from the Baylis-Hillman adducts via the sequential introduction of primary nitroalkane at the primary position, Michael addition to beta-branched Michael acceptor, aldol condensation, elimination of nitrous acid, and the final aromatization process. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.06.180

文献信息

• Regioselective synthesis of polysubstituted benzenes from Baylis–Hillman adducts via [4+2] annulation protocol
  作者：Mi Jung Lee、Ka Young Lee、Da Yeon Park、Jae Nyoung Kim

  DOI：10.1016/j.tet.2006.01.028

  日期：2006.3

  A new and regioselective [4+2] benzannulation protocol toward polysubstituted benzenes was developed. A nitroalkane derivative, which was prepared from Baylis–Hillman adduct, served as the four-carbon unit and a Michael acceptor as a two-carbon unit. Vinyltriphenylphosphonium salt could also be used as a Michael acceptor efficiently.

  开发了一种针对多取代苯的新的区域选择性[4 + 2]苯环芳烃方案。由Baylis–Hillman加合物制备的硝基烷衍生物用作四碳单元，而Michael受体用作二碳单元。乙烯基三苯基phosph盐也可以有效地用作迈克尔受体。
• Regioselective construction of polysubstituted benzene ring from Baylis–Hillman adduct via [4+2] annulation strategy
  作者：Mi Jung Lee、Ka Young Lee、Saravanan Gowrisankar、Jae Nyoung Kim

  DOI：10.1016/j.tetlet.2005.12.032

  日期：2006.2

  A new and regioselective [4+2] benzannulation protocol toward polysubstituted benzenes was developed. Nitroalkane derivative, which was prepared from Baylis-Hillman adduct, served as the four-carbon unit and Michael acceptor as a two-carbon unit. (c) 2005 Elsevier Ltd. All rights reserved.
• Regioselective synthesis of pentasubstituted benzene derivatives: TBAF as an effective catalyst for the sequential Michael addition-intramolecular aldolization
  作者：Da Yeon Park、Saravanan Gowrisankar、Jae Nyoung Kim

  DOI：10.1016/j.tetlet.2006.06.180

  日期：2006.9

  Polysubstituted benzene derivatives were synthesized starting from the Baylis-Hillman adducts via the sequential introduction of primary nitroalkane at the primary position, Michael addition to beta-branched Michael acceptor, aldol condensation, elimination of nitrous acid, and the final aromatization process. (c) 2006 Elsevier Ltd. All rights reserved.