α-Heptyl-N-benzylnitrone | 72552-76-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: α-Heptyl-N-benzylnitrone
• 英文别名: (Z)-N-benzyloctan-1-imine oxide；octanal-(N-benzyl oxime )；Benzyl-octyliden-aminoxid；Octanal-(N-benzyl-oxim)；N-benzyloctan-1-imine oxide
• CAS: 72552-76-2
• 化学式: C₁₅H₂₃NO
• 分子量: 233.354
• InChiKey: ORDGRVQBZVTAQE-SSZFMOIBSA-N

物化性质

• 熔点：
  87 °C
• 沸点：
  416.4±15.0 °C(Predicted)
• 密度：
  0.945±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.13
• 重原子数：
  17.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  26.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  α-Heptyl-N-benzylnitrone 在 lithium aluminium deuteride 、 臭氧 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 benzyl alcohol-d1
  参考文献：
  名称：

  Synthesis and x-ray analysis of dihydro-1,2,4,5-trioxazine. Evidence of a stepwise mechanism for the [3 + 3] cycloaddition of carbonyl oxides with nitrones

  摘要：

  Carbonyl oxides, derived by ozonolysis of vinyl ethers, readily undergo [3 + 3] cycloaddition reactions with nitrones affording dihydro-1,2,4,5-trioxazines in fair to excellent yield. The structures of dihydro-3,5,6-triphenyl-1,2,4,5-trioxazine (5f) and dihydro-3-cyclohexyl-5-methyl-6,6-diphenyl-1,2,4,5-trioxazine (5t) were unambiguously determined by X-ray analysis. Ozonolysis of 1-cyclohexyl-2-methoxyethene in the presence of either (E)- or (Z)-alpha-(4-methylphenyl)-alpha-phenyl-N-methylnitrone gave a 1:1 mixture of two stereoisomeric cycloadducts. This result, in conjunction with the structure of the relevant 5t, suggests that the [3 + 3] cycloaddition proceeds by a stepwise mechanism.

  DOI：

  10.1021/jo00034a018
• 作为产物：
  描述：

  trans-Dihydro-3-phenyl-5-(phenylmethyl)-6-heptyl-1,2,4,5-trioxazine 在 三苯基膦 作用下， 以 苯 为溶剂， 反应 90.0h， 以17%的产率得到α-Heptyl-N-benzylnitrone
  参考文献：
  名称：

  Synthesis and x-ray analysis of dihydro-1,2,4,5-trioxazine. Evidence of a stepwise mechanism for the [3 + 3] cycloaddition of carbonyl oxides with nitrones

  摘要：

  Carbonyl oxides, derived by ozonolysis of vinyl ethers, readily undergo [3 + 3] cycloaddition reactions with nitrones affording dihydro-1,2,4,5-trioxazines in fair to excellent yield. The structures of dihydro-3,5,6-triphenyl-1,2,4,5-trioxazine (5f) and dihydro-3-cyclohexyl-5-methyl-6,6-diphenyl-1,2,4,5-trioxazine (5t) were unambiguously determined by X-ray analysis. Ozonolysis of 1-cyclohexyl-2-methoxyethene in the presence of either (E)- or (Z)-alpha-(4-methylphenyl)-alpha-phenyl-N-methylnitrone gave a 1:1 mixture of two stereoisomeric cycloadducts. This result, in conjunction with the structure of the relevant 5t, suggests that the [3 + 3] cycloaddition proceeds by a stepwise mechanism.

  DOI：

  10.1021/jo00034a018

文献信息

• Synthesis and x-ray analysis of 1,2,4,5-trioxazinane
  作者：Mitsuyuki Mori、Tomohito Sugiyama、Masatomo Nojima、Shigekazu Kusabayashi、Kevin J. McCullough

  DOI：10.1021/ja00199a083

  日期：1989.8

  L'heterocycle du titre a ete synthetise par cycloaddition de nitrones au produit d'ozonolyse d'enols ethers

  L'heterocycle du titre a ete synthetise par cycloaddition de nitrones au produit d'ozonolyse d'enols ethers
• A Convenient Synthesis of Novel Isoxazolidine and Isoxazole Isoquinolinones Fused Hybrids
  作者：Konstantinos A. Ouzounthanasis、Stergios R. Rizos、Alexandros E. Koumbis

  DOI：10.3390/molecules29010091

  日期：——

  2-propargylbenzamide, respectively. The construction of the isoquinolinone lactam system followed by performing a selective Schmidt reaction for isoxazolidine derivatives (two steps overall), whereas the isoxazole lactams were reached via an Ullmann-type cyclisation (three steps overall). Key observations were made regarding the stereo- and regioselectivities of the reactions employed, and small libraries of

  异恶唑烷、异恶唑和异喹啉酮环存在于几种天然产物和/或药学上感兴趣的化合物的结构中。在这项工作中，已经开发了简便有效的途径来制备带有这些杂环的稠合框架。异恶唑烷/异喹啉酮和异恶唑/异喹啉酮杂化合成的成功方法最初依赖于硝酮和氧化腈分别与茚酮和2-炔丙基苯甲酰胺的1,3-偶极环加成。构建异喹啉酮内酰胺系统，然后对异恶唑烷衍生物进行选择性施密特反应（总共两步），而异恶唑内酰胺是通过乌尔曼型环化得到的（总共三步）。对所用反应的立体和区域选择性进行了关键观察，并制备了目标杂交体的小型文库，证明了这些策略的普遍适用性。
• Nerdel; Huldschinsky, Chemische Berichte, 1953, vol. 86, p. 1005,1010
  作者：Nerdel、Huldschinsky

  DOI：——

  日期：——
• Synthesis and x-ray analysis of dihydro-1,2,4,5-trioxazine. Evidence of a stepwise mechanism for the [3 + 3] cycloaddition of carbonyl oxides with nitrones
  作者：Mitsuyuki Mori、Tomohito Sugiyama、Masatomo Nojima、Shigekazu Kusabayashi、Kevin J. McCullough

  DOI：10.1021/jo00034a018

  日期：1992.4

  Carbonyl oxides, derived by ozonolysis of vinyl ethers, readily undergo [3 + 3] cycloaddition reactions with nitrones affording dihydro-1,2,4,5-trioxazines in fair to excellent yield. The structures of dihydro-3,5,6-triphenyl-1,2,4,5-trioxazine (5f) and dihydro-3-cyclohexyl-5-methyl-6,6-diphenyl-1,2,4,5-trioxazine (5t) were unambiguously determined by X-ray analysis. Ozonolysis of 1-cyclohexyl-2-methoxyethene in the presence of either (E)- or (Z)-alpha-(4-methylphenyl)-alpha-phenyl-N-methylnitrone gave a 1:1 mixture of two stereoisomeric cycloadducts. This result, in conjunction with the structure of the relevant 5t, suggests that the [3 + 3] cycloaddition proceeds by a stepwise mechanism.