4-环庚烯酮肟 | 65113-00-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 4-环庚烯酮肟
• 英文名称: 4-cycloheptenone oxime
• 英文别名: 4-Cycloheptenon-oxim；N-cyclohept-4-en-1-ylidenehydroxylamine
• CAS: 65113-00-0
• 化学式: C₇H₁₁NO
• 分子量: 125.17
• InChiKey: NWWNCOJJLIQYSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  32.6
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2928000090

反应信息

• 作为反应物：
  描述：

  4-环庚烯酮肟 在 盐酸 、 methyl orange 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以72%的产率得到1-hydroxylamino-4-cycloheptene
  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
• 作为产物：
  描述：

  4-环庚烯-1-酮 在 盐酸羟胺 、 sodium carbonate 作用下， 以 甲醇 为溶剂， 以85%的产率得到4-环庚烯酮肟
  参考文献：
  名称：

  通过Pd催化的分子内氨基羰基化反应正式合成（±）-铁精氨酸

  摘要：

  已经开发了一种实用且有效的合成途径来生产神经活性生物碱铁蛋白。8-氮杂二环[3.2.1]辛烷骨架4在一个步骤中通过分子内氨基羰基化，制备3通过钯催化。

  DOI：

  10.1016/s0040-4039(97)00575-3

文献信息

• A formal total synthesis of (±)-ferruginine by Pd-catalyzed intramolecular aminocarbonylation
  作者：Won-Hun Ham、Young Hoon Jung、Kyunghae Lee、Chang-Young Oh、Kee-Young Lee

  DOI：10.1016/s0040-4039(97)00575-3

  日期：1997.5

  A practical and efficient synthetic route to the neuroactive alkaloid ferruginine has been developed. 8-Azabicyclo[3.2.1]octane skeleton 4 was prepared in one step by intramolecular aminocarbonylation of 3 catalyzed by palladium.

  已经开发了一种实用且有效的合成途径来生产神经活性生物碱铁蛋白。8-氮杂二环[3.2.1]辛烷骨架4在一个步骤中通过分子内氨基羰基化，制备3通过钯催化。
• WILSON S. R.; SAWACKI R. A., J. ORG. CHEM., 1979, 44 NO 2, 287-291
  作者：WILSON S. R.、 SAWACKI R. A.

  DOI：——

  日期：——
• 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.