(S)-(1-cyclohexyl-2-nitroethyl)benzene | 1370408-18-6

• 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: (S)-(1-cyclohexyl-2-nitroethyl)benzene
• 英文别名: (1-cyclohexyl-2-nitroethyl)benzene；2-cyclohexyl-2-phenyl-1-nitroethane
• CAS: 1370408-18-6
• 化学式: C₁₄H₁₉NO₂
• 分子量: 233.31
• InChiKey: TZTRDTBKXCAUMM-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.63
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  43.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  2-cyclohexyl-1-nitroethene 、 苯硼酸 在 chloro(ethylene)rhodium(I) dimer 、 C₄₇H₅₅O₇P 、 potassium hydroxide 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以91%的产率得到(S)-(1-cyclohexyl-2-nitroethyl)benzene
  参考文献：
  名称：

  脱氧胆酸衍生的联芳基亚磷酸酯在铑催化的芳基硼酸与硝基烯烃的共轭加成反应中作为通用和对映体选择性配体。

  摘要：

  AbstractA highly enantioselective conjugate addition of arylboronic acids to cyclic as well as acyclic aromatic and aliphatic nitroalkenes is presented. The rhodium complexes obtained from deoxycholic acid‐derived binaphthyl and flexible biphenyl phosphites showed good activity as well as very high enantioselectivity (ee up to 99%) in the conjugated addition even in the presence of challenging substrates such as 1‐nitrocyclohexene or aliphatic acyclic nitroalkenes.magnified image

  DOI：

  10.1002/adsc.201300619

文献信息

• Heterogeneous Chiral Diene‐Rh Complexes for Asymmetric Arylation of α,β‐Unsaturated Carbonyl Compounds, Nitroalkenes, and Imines
  作者：Tatsuya Kuremoto、Tomohiro Yasukawa、Shū Kobayashi

  DOI：10.1002/adsc.201900526

  日期：2019.8.21

  A chiral diene ligand with tertiary alkyl amine‐derived secondary amide moiety was immobilized on cross‐linked polystyrene (PS) by radical polymerization, which was combined with Rh to form heterogeneous chiral Rh complexes (PS‐diene Rh−Cl). PS‐diene Rh−Cl catalyzed asymmetric arylation reactions of α,β‐unsaturated carbonyl compounds (ketones, esters, and amides), nitroalkenes, and imines afforded

  通过自由基聚合将具有叔烷基胺衍生的仲酰胺部分的手性二烯配体固定在交联的聚苯乙烯（PS）上，然后与Rh结合形成异质的手性Rh络合物（PS-diene Rh-Cl）。PS-二烯Rh-Cl催化的α，β-不饱和羰基化合物（酮，酯和酰胺），硝基烯烃和亚胺的不对称芳基化反应以高收率提供了所需的产物，并具有出色的对映选择性。PS-二烯Rh-Cl在空气中稳定，可以存放几个月，可以重复使用10次以上，而不会降低收率或对映选择性。我们还开发了一种活化PS-二烯Rh-Cl以生成更多活性物质的方法。
• 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 Addition of Arylboronic Acids to β-Nitroolefins: Formal Synthesis of (<i>S</i>)-SKF 38393
  作者：Kung-Chih Huang、Balraj Gopula、Ting-Shen Kuo、Chien-Wei Chiang、Ping-Yu Wu、Julian P. Henschke、Hsyueh-Liang Wu

  DOI：10.1021/ol4027599

  日期：2013.11.15

  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.