(S)-benzyl[2-(2-methyloctyl)phenyl]amine

• 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)-benzyl[2-(2-methyloctyl)phenyl]amine
• 英文别名: benzyl-[2-(2-methyloctyl)phenyl]amine；N-benzyl-2-[(2S)-2-methyloctyl]aniline
• 化学式: C₂₂H₃₁N
• 分子量: 309.495
• InChiKey: MAEWVHUQOUYXIE-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  N-苄基-2-溴苯胺 在 四(三苯基膦)钯 sodium carbonate 、 苯基锂 作用下， 以 乙二醇二甲醚 、 二丁醚 、 水 为溶剂， 反应 24.25h， 生成 (S)-benzyl[2-(2-methyloctyl)phenyl]amine
  参考文献：
  名称：

  Enantioselective Carbolithiation Initiated Cascade Reactions

  摘要：

  Enantioselective cascade reactions are very powerful synthetic protocols for the assembly of complex architectures. Our current approach is to exploit a (-)-sparteine-controlled enantioselective carbolithiation of 2-propenylarylamines to provide chiral intermediates, which depending upon choice of electrophile are subsequently in situ converted into products of increasing complexity. The chiral center, formed in high enantiomeric ratio in the first carbolithiation step, is carried through the cascade reaction sequence to the final products and is independent of electrophile used. The scope of the cascade reaction is outlined in terms of reaction conditions, alkyllithiums, and electrophiles.

  DOI：

  10.1021/ja060076g

文献信息

• Asymmetric Cascade Reaction Sequences via Chiral Lithiated Intermediates
  作者：Anne-Marie L. Hogan、Donal F. O'Shea

  DOI：10.1021/jo702290f

  日期：2008.4.1

  generation of chiral lithiated intermediates which have broad synthetic potential. These intermediates have been exploited in a series of further in situ reactions with electrophiles to generate a collection of products each containing a common stereogenic center. The stereogenic center, formed in high enantiomeric ratio in the first carbolithiation step, is carried through the cascade reaction sequence

  该（ - ） -的金雀花碱介导的对映选择性分子间碳锂（ē）-2-丙烯基芳基胺可以产生具有广泛合成潜力的手性锂化中间体。这些中间体已在与亲电试剂的一系列其他原位反应中得到利用，以生成一系列产物，每个产物均包含一个共同的立体异构中心。在第一步碳烷化步骤中以高对映体比例形成的立体异构中心通过级联反应序列传递至最终产物，并且与所用的亲电子试剂无关。该方法通过合成结构多样的手性苯胺，吲哚和吲哚酮以证明其er均为92：8（±1）。杂环合成涉及对映选择性烯烃碳环化，以及随后用合适的亲电试剂捕获中间有机锂，
• Enantioselective Carbolithiation Initiated Cascade Reactions
  作者：Anne-Marie L. Hogan、Donal F. O'Shea

  DOI：10.1021/ja060076g

  日期：2006.8.1

  Enantioselective cascade reactions are very powerful synthetic protocols for the assembly of complex architectures. Our current approach is to exploit a (-)-sparteine-controlled enantioselective carbolithiation of 2-propenylarylamines to provide chiral intermediates, which depending upon choice of electrophile are subsequently in situ converted into products of increasing complexity. The chiral center, formed in high enantiomeric ratio in the first carbolithiation step, is carried through the cascade reaction sequence to the final products and is independent of electrophile used. The scope of the cascade reaction is outlined in terms of reaction conditions, alkyllithiums, and electrophiles.