1-nitro-2-(1(E)-octenyl)cyclohexene | 132839-75-9

• 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: 1-nitro-2-(1(E)-octenyl)cyclohexene
• 英文别名: 1-nitro-2-[(E)-oct-1-enyl]cyclohexene
• CAS: 132839-75-9
• 化学式: C₁₄H₂₃NO₂
• 分子量: 237.342
• InChiKey: RXFZLFKPFLGPDN-JXMROGBWSA-N

物化性质

• 沸点：
  353.3±12.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  反式-1-碘-1-辛烯 、 1-ethylthio-2-nitrocyclohexene 生成 1-nitro-2-(1(E)-octenyl)cyclohexene
  参考文献：
  名称：

  Preparation of polyfunctional nitro olefins and nitroalkanes using the copper-zinc reagents RCu(CN)ZnI

  摘要：

  The addition of the copper-zinc reagents RCu(CN)ZnX to a variety of nitro olefins produces polyfunctional nitroalkanes in high yields. The intermediate zinc or copper nitronates can be directly submitted to a Nef reaction (O3,-78-degrees-C) and converted to polyfunctional ketones in a one-pot procedure. The addition of RCu(CN)ZnX to nitro olefins bearing a leaving group (RSO2, RS) in the beta-position provides pure (E)-nitro olefins in excellent yields. The reaction has been applied for the stereoselective preparation of 1,3-nitrodienes and for a Diels-Alder reaction precursor.

  DOI：

  10.1021/jo00046a027

文献信息

• Highly stereoselective preparation of nitro olefins and nitro dienes by the addition-elimination of copper-zinc organometallics to β-alkylthio and β-phenylsulfonyl nitro olefins
  作者：Carole Retherford、Paul Knochel

  DOI：10.1016/s0040-4039(00)79462-7

  日期：1991.1

  onyl ethylene 2a gave highly functionalized pure (E) nitro olefins and stereoselectively (1E, 3E) and (1E, 3Z)-1-nitrodienes in excellent yields. β-Alkylthio nitro olefins such as 2-ethylthio-1-nitro-1-cyclohexene 2b and 2,2-dimethylthio-1-nitroethylene 12 were found to have a similar behavior. This methodology allowed an expeditive preparation of the triene 5 which underwent an extremely mild silica

  将铜锌有机金属RCu（CN）ZnX加成消除至（E）-1-硝基-2-苯基磺酰基乙烯2a，得到高度官能化的纯（E）硝基烯烃，并立体选择性地（1E，3E）和（1E，3Z） -1-硝基二烯的收率极高。发现β-烷硫基硝基烯烃如2-乙基硫基-1-硝基-1-环己烯2b和2，2-二甲基硫基-1-硝基乙烯12具有相似的行为。该方法学允许快速地制备三烯5，该三烯5经历了极其温和的硅胶催化的立体定向Diels-Alder环化。
• Preparation of polyfunctional nitro olefins and nitroalkanes using the copper-zinc reagents RCu(CN)ZnI
  作者：Carole Jubert、Paul Knochel

  DOI：10.1021/jo00046a027

  日期：1992.9

  The addition of the copper-zinc reagents RCu(CN)ZnX to a variety of nitro olefins produces polyfunctional nitroalkanes in high yields. The intermediate zinc or copper nitronates can be directly submitted to a Nef reaction (O3,-78-degrees-C) and converted to polyfunctional ketones in a one-pot procedure. The addition of RCu(CN)ZnX to nitro olefins bearing a leaving group (RSO2, RS) in the beta-position provides pure (E)-nitro olefins in excellent yields. The reaction has been applied for the stereoselective preparation of 1,3-nitrodienes and for a Diels-Alder reaction precursor.