(2E)-2-(硝基甲基烯)双环[2.2.1]庚烷 | 349490-90-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: (2E)-2-(硝基甲基烯)双环[2.2.1]庚烷
• 英文名称: 2-nitromethylene-bicyclo[2.2.1]heptane
• 英文别名: Bicyclo[2.2.1]heptane, 2-(nitromethylene)-；2-(nitromethylidene)bicyclo[2.2.1]heptane
• CAS: 349490-90-0
• 化学式: C₈H₁₁NO₂
• 分子量: 153.181
• InChiKey: MCOTUEWHNPYKBA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  邻甲基苄醇 、 (2E)-2-(硝基甲基烯)双环[2.2.1]庚烷 在 三乙烯二胺 作用下， 反应 37.0h， 以49%的产率得到
  参考文献：
  名称：

  The Synthesis of 2,2-Disubstituted-3-nitrochromenes from Salicylaldehyde and 2,2-Disubstituted-1-nitroalkenes

  摘要：

  DOI：

  10.3987/com-02-9454
• 作为产物：
  描述：

  降樟脑 在 双氧水 、 乙二胺 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 18.0h， 生成 (2E)-2-(硝基甲基烯)双环[2.2.1]庚烷
  参考文献：
  名称：

  A one-pot, two step synthesis of 2,2-disubstituted 1-nitroalkenes

  摘要：

  The reactions of ketones 1a-o, nitromethane 2, and a stoichiometric amount of piperidine 3a or ethylenediamine 3b in the presence of mercaptan 6a in THF or CH3CN solution give high yields of beta-nitrosulfides 7a-o. The latter can be oxidized by 8a (m-CPBA or m-CPBA/AcOH) at 0degreesC, 8b (H2O2/AcOH), or 8c (H2O2) at room temperature, thus generating beta-nitroalkylsulfoxides 9a-o, which then undergo elimination to produce medium to high yields of 2,2-disubstituted-1-nitroalkenes 5a-o, when refluxed in a solution of ClCH2CH2Cl (1,2-dichloroethane). After preparation from 1a-o, 2, 3, and 6a, 7a-o were oxidized with 8a, 8b, or 8c in a mixture of CH3CN and ClCH2CH2Cl to generate beta-nitrosulfoxides 9a-o, which then underwent elimination under refluxing under one-pot conditions. Compounds 14 and 15g were also prepared using 13, 2, 3b, and 6, in a similar manner. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00754-3

文献信息

• A one-pot, two step synthesis of 2,2-disubstituted 1-nitroalkenes
  作者：Yeong-Jiunn Jang、Wen-Wei Lin、Yuh-Kuo Shih、Ju-Tsung Liu、Ming-Hsing Hwang、Ching-Fa Yao

  DOI：10.1016/s0040-4020(03)00754-3

  日期：2003.6

  The reactions of ketones 1a-o, nitromethane 2, and a stoichiometric amount of piperidine 3a or ethylenediamine 3b in the presence of mercaptan 6a in THF or CH3CN solution give high yields of beta-nitrosulfides 7a-o. The latter can be oxidized by 8a (m-CPBA or m-CPBA/AcOH) at 0degreesC, 8b (H2O2/AcOH), or 8c (H2O2) at room temperature, thus generating beta-nitroalkylsulfoxides 9a-o, which then undergo elimination to produce medium to high yields of 2,2-disubstituted-1-nitroalkenes 5a-o, when refluxed in a solution of ClCH2CH2Cl (1,2-dichloroethane). After preparation from 1a-o, 2, 3, and 6a, 7a-o were oxidized with 8a, 8b, or 8c in a mixture of CH3CN and ClCH2CH2Cl to generate beta-nitrosulfoxides 9a-o, which then underwent elimination under refluxing under one-pot conditions. Compounds 14 and 15g were also prepared using 13, 2, 3b, and 6, in a similar manner. (C) 2003 Elsevier Science Ltd. All rights reserved.
• The Synthesis of 2,2-Disubstituted-3-nitrochromenes from Salicylaldehyde and 2,2-Disubstituted-1-nitroalkenes
  作者：Ching-Fa Yao、Ming-Chung Yan、Yeong-Jiunn Jang、Wen-Yu Kuo、Zhijay Tu、Kao-Hsien Shen、Ting-Shen Cuo、Chuen-Her Ueng

  DOI：10.3987/com-02-9454

  日期：——