4-(cyclohept-1-enecarbonyl)-morpholine | 91554-20-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: 4-(cyclohept-1-enecarbonyl)-morpholine
• 英文别名: Cyclohept-1-en-carbonsaeure-morpholid；Cyclohepten-1-yl(morpholin-4-yl)methanone
• CAS: 91554-20-0
• 化学式: C₁₂H₁₉NO₂
• 分子量: 209.288
• InChiKey: UYCSPRNZSHLPFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(cyclohept-1-enecarbonyl)-morpholine 在 正丁基锂 、 silica gel 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.5h， 生成 (3aR,8aS)-8a-(2,2-Dimethoxy-ethylamino)-2-methoxy-3-[(triisopropylsilanyl)-methyl]-4,5,6,7,8,8a-hexahydro-3aH-azulen-1-one
  参考文献：
  名称：

  Interrupted Nazarov Cyclization on Silica Gel

  摘要：

  Exposure of a mixture of propargyl vinyl ketone and a nucleophilic primary or secondary amine to activated dry silica gel in the absence of solvent leads to a cascade of reactions that results in the formation of an aminocyclopentenone. The reaction with triethylamine leads to a cross-conjugated cyclopentadienone.

  DOI：

  10.1021/ja053393g
• 作为产物：
  描述：

  1-hydroxy-cycloheptanecarbonitrile 在 吡啶 、 sodium hydroxide 、 草酰氯 、 四丁基硫酸氢铵 、 N,N-二甲基甲酰胺 、 三氯氧磷 作用下， 以 乙醇 、 水 为溶剂， 生成 4-(cyclohept-1-enecarbonyl)-morpholine
  参考文献：
  名称：

  Tandem alkylation–cyclization process via an O,C-dianion

  摘要：

  A general protocol for preparing densely functionalized cyclopentenones through a tandem nucleophilic addition-deprotonation-alkylation-cyclization process is described. Addition of lithioallene 2 to enamides 1 generates tetrahedral intermediate 3. Deprotonation of the gamma carbon atom of the allene function in situ, followed by trapping by a suitable electrophile and cyclization during workup leads to C6 substituted cyclopentenones 6. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.097

文献信息

• Asymmetric Amine-Intercepted Nazarov Cyclization
  作者：Francis Dhoro、Tor E. Kristensen、Vegar Stockmann、Glenn P. A. Yap、Marcus A. Tius

  DOI：10.1021/ja0718873

  日期：2007.6.13

  The chiral auxiliary directed addition of a propargyllithium reagent to a morpholino enamide, followed by exposure of the adduct to activated dry Florisil in the absence of solvent and in the presence of a primary or secondary amine, leads to a cascade of reactions that results in the formation of an aminocyclopentenone as a single diastereoisomer. The reaction can also be conducted intramolecularly.
• Asymmetric Cyclopentannelation:  Camphor-Derived Auxiliary
  作者：Paul E. Harrington、Tsuyoshi Murai、Chester Chu、Marcus A. Tius

  DOI：10.1021/ja020591o

  日期：2002.8.1

  The scope of an enantioselective cyclopentannelation reaction that makes use of allenyl ether-derived nucleophiles has been probed. The enantioselectivity is induced by a traceless chiral auxiliary that is easily derived from camphor. It has been shown that for gamma-substituted allene ethers that are axially chiral, very high enantiomeric excesses of cyclopentenone products are observed in the matched cases. Two fundamentally different mechanisms are observed, one for the cyclizations of allenyl ketones (see eq 7), the other for the cyclizations of allenyl alcohols (see eq 11). The methodology is versatile, efficient, and well-suited for applications in synthesis.
• Tandem alkylation–cyclization process via an O,C-dianion
  作者：April R. Banaag、Gideon O. Berger、Francis Dhoro、Derrick B. delos Santos、Darryl D. Dixon、James P. Mitchell、Bradley K. Tokeshi、Marcus A. Tius

  DOI：10.1016/j.tet.2005.01.097

  日期：2005.3

  A general protocol for preparing densely functionalized cyclopentenones through a tandem nucleophilic addition-deprotonation-alkylation-cyclization process is described. Addition of lithioallene 2 to enamides 1 generates tetrahedral intermediate 3. Deprotonation of the gamma carbon atom of the allene function in situ, followed by trapping by a suitable electrophile and cyclization during workup leads to C6 substituted cyclopentenones 6. (c) 2005 Elsevier Ltd. All rights reserved.
• Interrupted Nazarov Cyclization on Silica Gel
  作者：Francis Dhoro、Marcus A. Tius

  DOI：10.1021/ja053393g

  日期：2005.9.1

  Exposure of a mixture of propargyl vinyl ketone and a nucleophilic primary or secondary amine to activated dry silica gel in the absence of solvent leads to a cascade of reactions that results in the formation of an aminocyclopentenone. The reaction with triethylamine leads to a cross-conjugated cyclopentadienone.