(Z)-tetraethyl 4-(1-(benzylamino)-1-oxopropan-2-ylidene)-5-methylenecyclohexane-1,1,2,2-tetracarboxylate | 1187438-47-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (Z)-tetraethyl 4-(1-(benzylamino)-1-oxopropan-2-ylidene)-5-methylenecyclohexane-1,1,2,2-tetracarboxylate
• 英文别名: tetraethyl (4Z)-4-[1-(benzylamino)-1-oxopropan-2-ylidene]-5-methylidenecyclohexane-1,1,2,2-tetracarboxylate
• CAS: 1187438-47-6
• 化学式: C₂₉H₃₇NO₉
• 分子量: 543.614
• InChiKey: BONHULNDJPSJOU-XDOYNYLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  39
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  134
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (Z)-tetraethyl 4-(1-(benzylamino)-1-oxopropan-2-ylidene)-5-methylenecyclohexane-1,1,2,2-tetracarboxylate 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以53%的产率得到(E)-tetraethyl 2-(benzylimino)-7a-(bromomethyl)-3-methyl-7,7a-dihydrobenzofuran-5,5,6,6(2H,4H)-tetracarboxylate
  参考文献：
  名称：

  Nickel-Catalyzed Cycloadditive Couplings of Enynes and Isocyanates

  摘要：

  A mild and general route for preparing dienamides is described. Nickel imidazolylidene complexes were used to mediate cycloadditive coupling between enynes and isocyanates. Dienamides were prepared in excellent yields and with good E:Z selectivity. These dienamides can be further manipulated through oxidative cyclization methods. When a terminal enyne is employed, cyclization affords a lactam rather than a dienamide.

  DOI：

  10.1021/ol901703t
• 作为产物：
  描述：

  2-allyl-2,3,3-tris-ethoxycarbonyl-hept-5-ynoic acid ethyl ester 、 异氰酸苄酯 在 bis(1,5-cyclooctadiene)nickel (0) 、 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 (E)-tetraethyl 4-(1-(benzylamino)-1-oxopropan-2-ylidene)-5-methylenecyclohexane-1,1,2,2-tetracarboxylate 、 (Z)-tetraethyl 4-(1-(benzylamino)-1-oxopropan-2-ylidene)-5-methylenecyclohexane-1,1,2,2-tetracarboxylate
  参考文献：
  名称：

  Nickel-Catalyzed Cycloadditive Couplings of Enynes and Isocyanates

  摘要：

  A mild and general route for preparing dienamides is described. Nickel imidazolylidene complexes were used to mediate cycloadditive coupling between enynes and isocyanates. Dienamides were prepared in excellent yields and with good E:Z selectivity. These dienamides can be further manipulated through oxidative cyclization methods. When a terminal enyne is employed, cyclization affords a lactam rather than a dienamide.

  DOI：

  10.1021/ol901703t