(S)-1-(1-cyclohexyl-2-nitroethyl)-4-methoxybenzene | 1370408-19-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (S)-1-(1-cyclohexyl-2-nitroethyl)-4-methoxybenzene
• 英文别名: 1-(1-cyclohexyl-2-nitroethyl)-4-methoxybenzene
• CAS: 1370408-19-7
• 化学式: C₁₅H₂₁NO₃
• 分子量: 263.337
• InChiKey: OACJZUYZGPZAHC-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.64
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  52.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  4-甲氧基苯硼酸 、 2-硝基乙烯基环己烷 在 potassium hydrogen difluoride 、 C₆₀H₅₂Cl₂Rh₂ 作用下， 以 水 、 甲苯 为溶剂， 反应 18.0h， 以85%的产率得到
  参考文献：
  名称：

  Rhodium-Catalyzed Asymmetric Addition of Arylboronic Acids to β-Nitroolefins: Formal Synthesis of (S)-SKF 38393

  摘要：

  An efficient enantioselective addition of an array of arylboronic acids to various beta-nitrostyrenes catalyzed by a novel and reactive rhodium-diene catalyst (S/C up to 1000) was developed, providing beta,beta-diarylnitroethanes in good to high yields (62-99%) with excellent enantioselectivities (85-97% ee). The method was extended to 2-heteroarylnitroolefins and 2-alkylnitroolefins similarly providing the desired products with high enantioselectivities and yields. The usefulness of this method was demonstrated in the formal synthesis of the enantiomer of the dopamine receptor agonist and antagonist, SKF 38393.

  DOI：

  10.1021/ol4027599

文献信息

• Rhodium-Catalyzed Asymmetric Conjugate Addition of Arylboronic Acids to Nitroalkenes Using Olefin–Sulfoxide Ligands
  作者：Feng Xue、Dongping Wang、Xincheng Li、Boshun Wan

  DOI：10.1021/jo3003562

  日期：2012.4.6

  An efficient rhodium/olefin–sulfoxide catalyzed asymmetric conjugate addition of organoboronic acids to a variety of nitroalkenes has been developed, where 2-methoxy-1-naphthyl sulfinyl functionalized olefin ligands have shown to be highly effective and are applicable to a broad scope of aryl, alkyl, and heteroaryl nitroalkenes.

  已经开发出一种有效的铑/烯烃-亚砜催化的有机硼酸向各种硝基烯烃的不对称共轭加成反应，其中2-甲氧基-1-萘亚磺酰基官能化的烯烃配体已被证明是高效的，适用于广泛的芳基，烷基和杂芳基硝基烯烃。
• Rhodium-Catalyzed Asymmetric Conjugate Addition of Organoboronic Acids to Nitroalkenes Using Chiral Bicyclo[3.3.0] Diene Ligands
  作者：Zhi-Qian Wang、Chen-Guo Feng、Shu-Sheng Zhang、Ming-Hua Xu、Guo-Qiang Lin

  DOI：10.1002/anie.201001883

  日期：——

  Old before I diene: An efficient rhodium/diene‐catalyzed asymmetric conjugate addition of organoboronic acids to challenging nitroalkene substrates that lack α substituents has been developed. Chiral bicyclo[3.3.0] dienes were found to be superior ligands under ArB(OH)2/KHF2 conditions. Np=naphthyl.

  在二烯之前就已陈旧：已经开发出一种有效的铑/二烯催化的不对称α-取代基的富挑战性硝基烯烃底物的有机硼酸不对称共轭加成物。在ArB（OH）2 / KHF 2条件下，发现手性双环[3.3.0]二烯是优良的配体。Np ＝萘基。