2-己烯酸,6-(苯基甲氧基)-3-[(苯基甲基)氨基]-,乙基酯 | 154820-13-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-己烯酸,6-(苯基甲氧基)-3-[(苯基甲基)氨基]-,乙基酯
• 英文名称: (Z)-3-Benzylamino-6-benzyloxy-hex-2-enoic acid ethyl ester
• CAS: 154820-13-0
• 化学式: C₂₂H₂₇NO₃
• 分子量: 353.461
• InChiKey: LCVKHCMYVLQETP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.22
• 重原子数：
  26.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  47.56
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-己烯酸,6-(苯基甲氧基)-3-[(苯基甲基)氨基]-,乙基酯 在 palladium on activated charcoal 咪唑 、 lithium aluminium tetrahydride 、 氢气 、 lithium 、 sodium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 氨 、 N,N-二甲基甲酰胺 为溶剂， -33.0 ℃ 、303.98 kPa 条件下， 反应 50.0h， 生成 3-[(2R,3R)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-piperidin-2-yl]-propan-1-ol
  参考文献：
  名称：

  Heterocycle Formation through Aza-Annulation: Stereochemically Controlled Syntheses of (.+-.)-5-Epitashiromine and (.+-.)-Tashiromine

  摘要：

  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.

  DOI：

  10.1021/jo00086a009
• 作为产物：
  描述：

  1-苄氧基-2-碘乙烷 在 正丁基锂 、 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 正己烷 、 苯 为溶剂， 反应 13.75h， 生成 2-己烯酸,6-(苯基甲氧基)-3-[(苯基甲基)氨基]-,乙基酯
  参考文献：
  名称：

  Heterocycle Formation through Aza-Annulation: Stereochemically Controlled Syntheses of (.+-.)-5-Epitashiromine and (.+-.)-Tashiromine

  摘要：

  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.

  DOI：

  10.1021/jo00086a009