3-[1-Benzylamino-eth-(E)-ylidene]-dihydro-furan-2-one | 14142-03-1

• 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: 3-[1-Benzylamino-eth-(E)-ylidene]-dihydro-furan-2-one
• 英文别名: 3-[1-(Benzylamino)ethylidene]oxolan-2-one；3-[1-(benzylamino)ethylidene]oxolan-2-one
• CAS: 14142-03-1
• 化学式: C₁₃H₁₅NO₂
• 分子量: 217.268
• InChiKey: QVWKPQCFVGLHLG-UHFFFAOYSA-N

物化性质

• 沸点：
  411.5±45.0 °C(Predicted)
• 密度：
  1.157±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[1-Benzylamino-eth-(E)-ylidene]-dihydro-furan-2-one 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 氯仿 为溶剂， 反应 36.0h， 生成 2-[7-benzyl-6-methyl-1,8-dioxo-2-oxa-7-azaspiro[4.4]nonan-9-yl]acetic acid
  参考文献：
  名称：

  通过[3 + 2]和[3 + 3]氮杂环化反应轻松合成螺环内酰胺

  摘要：

  通过适当的烯胺与马来酸酐或衣康酸酐之间的氮杂环化反应，以非对映选择性的方式组装5,5-和5,6-螺环内酰胺。可用的起始原料以及简单的步骤可以考虑将合成的螺环化合物作为筛选库合成的视角构建基块。

  DOI：

  10.1002/ejoc.202100255
• 作为产物：
  描述：

  α-乙酰基-γ-丁内酯 、 苄胺 在 iron(III) trifluoromethanesulfonate 作用下， 反应 24.0h， 以60%的产率得到3-[1-Benzylamino-eth-(E)-ylidene]-dihydro-furan-2-one
  参考文献：
  名称：

  可见光通过β-烯丙基自由基中间体促进β-酮羰基的β-C-H烷基化

  摘要：

  在仲烯胺的光诱导单电子转移（SET）氧化的基础上报道了5πe羰基活化模式。生成的β-烯丙基自由基中间体被多种Michael受体捕获，从而以高效方式生成β-酮羰基的β-烷基化产物。

  DOI：

  10.1002/cjoc.201700785

文献信息

• Heterocycle Formation through Aza-Annulation: Stereochemically Controlled Syntheses of (.+-.)-5-Epitashiromine and (.+-.)-Tashiromine
  作者：K. Paulvannan、John R. Stille

  DOI：10.1021/jo00086a009

  日期：1994.4

  N-alkylenamines, stabilized through conjugation with an electron-withdrawing group, undergo aza-annulation with acryloyl chloride to provide a convergent route for the construction of six-membered nitrogen heterocycles. In addition to enhancing the C-alkylation process of annulation relative to the competing N-acylation process, the electron withdrawing substituent controlled the regioselectivity of alkene formation in both the intermediate enamine and in the unsaturated lactam product. A variety of functional groups, which include -COMe, -COPh, -CO(2)R, -CONHPh, -CN, -P(O)(OEt)(2), and -SO(2)Ph, were used to determine the effect of the electron-withdrawing substituents upon both the annulation reaction with acryloyl chloride and the subsequent hydrogenation process. When the enamide annulation product was stabilized through conjugation with ester or amide substituents, catalytic hydrogenation of the ate-annulation product resulted in the formation of vicinal stereocenters with high cis selectivity. The utility of this methodology was demonstrated by application of the condensation/aza-annulation/hydrogenation sequence as the key for construction and stereochemical control of the indolizidine ring system of (+/-)-tashiromine.
• Visible Light Promoted β-C-H Alkylation of β-Ketocarbonyls <i>via</i> a β-Enaminyl Radical Intermediate
  作者：Dehong Wang、Long Zhang、Sanzhong Luo

  DOI：10.1002/cjoc.201700785

  日期：2018.4

  carbonyl activation mode is reported on the basis of photo‐induced single‐electron‐transfer (SET) oxidation of a secondary enamine. The resultant β‐enaminyl radical intermediate was trapped by a wide range of Michael acceptors, producing β‐alkylation products of β‐ketocarbonyls in a highly efficient manner.

  在仲烯胺的光诱导单电子转移（SET）氧化的基础上报道了5πe羰基活化模式。生成的β-烯丙基自由基中间体被多种Michael受体捕获，从而以高效方式生成β-酮羰基的β-烷基化产物。
• Facile Synthesis of Spirocyclic Lactams via [3+2] and [3+3] Aza‐Annulation Reactions
  作者：Davit Hayrapetyan、Valeriya Stepanova

  DOI：10.1002/ejoc.202100255

  日期：2021.4.15

  5,5‐ and 5,6‐spirocyclic lactams were assembled in a diastereoselective manner via an aza‐annulation reaction between appropriate enamines and maleic or itaconic anhydrides. Available starting materials along with simple procedures are allowing for considering the resulting spirocycles as perspective building blocks for the synthesis of screening libraries.

  通过适当的烯胺与马来酸酐或衣康酸酐之间的氮杂环化反应，以非对映选择性的方式组装5,5-和5,6-螺环内酰胺。可用的起始原料以及简单的步骤可以考虑将合成的螺环化合物作为筛选库合成的视角构建基块。