Diethyl 7-cyclohexylidene-2,3-diazabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate | 916672-82-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: Diethyl 7-cyclohexylidene-2,3-diazabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate
• 英文别名: diethyl 7-cyclohexylidene-2,3-diazabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate
• CAS: 916672-82-7
• 化学式: C₁₇H₂₄N₂O₄
• 分子量: 320.389
• InChiKey: AXZTXMIMNADMSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Diethyl 7-cyclohexylidene-2,3-diazabicyclo[2.2.1]hept-5-ene-2,3-dicarboxylate 、 2-碘乙酰苯胺 在 三乙胺 、 三苯基膦 、 palladium dichloride 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以96%的产率得到diethyl 1-(2-(2-acetamidophenyl)-5-cyclohexylidenecyclopent-3-enyl)hydrazine-1,2-dicarboxylate
  参考文献：
  名称：

  通过钯催化的氮杂双环烯烃与芳基卤化物的开环， 独家生产3,4-二取代的环戊烯和亚烷基环戊烯†

  摘要：

  阐述了在钯催化下双环肼与各种芳基卤化物进行立体选择性开环的简单有效方法。反应以良好至优异的产率提供了反式-3，4-二取代的环戊烯或亚烷基环戊烯。通过利用合成的反式-3-苯基-4-肼基-环戊烯中的多个官能化点，我们合成了抗抑郁药Cypenamine（反式-2-苯基环戊胺）。

  DOI：

  10.1039/c3ra41504j

文献信息

• Palladium catalyzed reaction of ortho-functionalized aryl iodides with bicyclic hydrazines: facile route toward heteroannulated cyclopentenes and azabicycles
  作者：Jubi John、Rani Rajan、S. Sarath Chand、Praveen Prakash、Nayana Joseph、Eringathodi Suresh、K.V. Radhakrishnan

  DOI：10.1016/j.tet.2012.10.053

  日期：2013.1

  A palladium catalyzed tandem protocol for the synthesis of cyclopentene fused heterocycles from diazabicyclic alkenes and ortho-functionalized aryl iodides has been elaborated. This tandem protocol was utilized for the synthesis of a number of cyclopentene fused dihydrobenzofurans and indolines. The reaction can be tuned toward the formation of either 3,4-disubstituted cyclopentenes or cyclopentene fused heterocycles by careful manipulation of the reaction parameters. The reaction was also extended to bicyclic alkenes derived from fulvene, which resulted in the heteroannulation of the azabicyclic system. (C) 2012 Elsevier Ltd. All rights reserved.
• An exclusive approach to 3,4-disubstituted cyclopentenes and alkylidene cyclopentenes via the palladium catalyzed ring opening of azabicyclic olefins with aryl halides
  作者：Nayana Joseph、Rani Rajan、Jubi John、N. V. Devika、S. Sarath Chand、E. Suresh、Petri M. Pihko、K. V. Radhakrishnan

  DOI：10.1039/c3ra41504j

  日期：——

  A simple and efficient method for the stereoselective ring opening of bicyclic hydrazines with various aryl halides under palladium catalysis has been elaborated. The reactions afforded trans-3,4-disubstituted cyclopentenes or alkylidene cyclopentenes in good to excellent yields. By taking advantage of multiple points of functionalization in the synthesized trans-3-phenyl-4-hydrazino-cyclopentene,

  阐述了在钯催化下双环肼与各种芳基卤化物进行立体选择性开环的简单有效方法。反应以良好至优异的产率提供了反式-3，4-二取代的环戊烯或亚烷基环戊烯。通过利用合成的反式-3-苯基-4-肼基-环戊烯中的多个官能化点，我们合成了抗抑郁药Cypenamine（反式-2-苯基环戊胺）。