(Z)-5-methoxy-4-((tributylstannyl)methylene)-3,4-dihydro-2H-pyrrole | 1271100-02-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 甲亚胺酸及其衍生物
• 英文名称: (Z)-5-methoxy-4-((tributylstannyl)methylene)-3,4-dihydro-2H-pyrrole
• CAS: 1271100-02-7
• 化学式: C₁₈H₃₅NOSn
• 分子量: 400.192
• InChiKey: YEYZSFRUVUPTRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.75
• 重原子数：
  21
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-5-methoxy-4-((tributylstannyl)methylene)-3,4-dihydro-2H-pyrrole 、 苯甲醛 在 甲基锂 、 水 、 碳酸氢钠 作用下， 以 四氢呋喃 、 乙醚 、 甲基叔丁基醚 为溶剂， 反应 0.5h， 以97%的产率得到(Z)-2-(5-methoxy-2H-pyrrol-4(3H)-ylidene)-1-phenylethanol
  参考文献：
  名称：

  The Imidato-Alkenyllithium Route for the Synthesis of the Isoquinocycline-Pyrrolopyrrole Substructure

  摘要：

  A convergent and effective synthesis of the pyrrolopyrrole substructure (CDEFG) of the Isoquinocyclines Is reported. A key step is a tin lithium exchange of an imidato-alkenyltin compound (a ring G equivalent) and the subsequent acylation with a lactone. The resulting acetal is used successfully for the ring F closure to the pyrrolopyrrole. The sole formation of the isoquinocycline N,O-acetal epimer is in accordance with the proposed mechanism for the isomerization of quinocyclines to isoquinocyclines.

  DOI：

  10.1021/ol200085g

文献信息

• The Imidato-Alkenyllithium Route for the Synthesis of the Isoquinocycline-Pyrrolopyrrole Substructure
  作者：M. André Breuning、Klaus Harms、Ulrich Koert

  DOI：10.1021/ol200085g

  日期：2011.3.18

  A convergent and effective synthesis of the pyrrolopyrrole substructure (CDEFG) of the Isoquinocyclines Is reported. A key step is a tin lithium exchange of an imidato-alkenyltin compound (a ring G equivalent) and the subsequent acylation with a lactone. The resulting acetal is used successfully for the ring F closure to the pyrrolopyrrole. The sole formation of the isoquinocycline N,O-acetal epimer is in accordance with the proposed mechanism for the isomerization of quinocyclines to isoquinocyclines.