N-4-cycloheptenyl-C-methylnitrone | 1306607-34-0

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: N-4-cycloheptenyl-C-methylnitrone
• 英文别名: N-cyclohept-4-en-1-ylethanimine oxide
• CAS: 1306607-34-0
• 化学式: C₉H₁₅NO
• 分子量: 153.224
• InChiKey: QYOCKOUYFBXZTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  28.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-环庚烯-1-酮 在 盐酸 、 盐酸羟胺 、 methyl orange 、 sodium acetate 、 sodium cyanoborohydride 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 10.25h， 生成 N-4-cycloheptenyl-C-methylnitrone
  参考文献：
  名称：

  Entropy versus tether strain effects on rates of intramolecular 1,3-dipolar cycloadditions of N-alkenylnitrones

  摘要：

  Intramolecular 1,3-dipolar cycloadditions of two N-alkenylnitrones are studied by means of density functional theory calculations. Cycloaddition of an acyclic 4-hexenylnitrone led to the expected isoxazolidine in 46% yield, but a 4-cycloheptenylnitrone did not react. Calculations of the transition states for cycloaddition indicate that although the cycloheptenyl nitrone has a more favorable activation entropy, the strain associated with distortion of the tethering groups into the required boat conformation disfavors the reaction of the cyclic substrate over the acyclic substrate by 8.7 kcal/mol. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.11.121

文献信息

• Entropy versus tether strain effects on rates of intramolecular 1,3-dipolar cycloadditions of N-alkenylnitrones
  作者：Elizabeth H. Krenske、K.N. Houk、Andrew B. Holmes、John Thompson

  DOI：10.1016/j.tetlet.2010.11.121

  日期：2011.4

  Intramolecular 1,3-dipolar cycloadditions of two N-alkenylnitrones are studied by means of density functional theory calculations. Cycloaddition of an acyclic 4-hexenylnitrone led to the expected isoxazolidine in 46% yield, but a 4-cycloheptenylnitrone did not react. Calculations of the transition states for cycloaddition indicate that although the cycloheptenyl nitrone has a more favorable activation entropy, the strain associated with distortion of the tethering groups into the required boat conformation disfavors the reaction of the cyclic substrate over the acyclic substrate by 8.7 kcal/mol. (C) 2010 Elsevier Ltd. All rights reserved.