(E)-N-(1-(naphthalen-2-yl)ethylidene)prop-2-en-1-amine | 268556-64-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (E)-N-(1-(naphthalen-2-yl)ethylidene)prop-2-en-1-amine
• CAS: 268556-64-5
• 化学式: C₁₅H₁₅N
• 分子量: 209.291
• InChiKey: ALLPHIOMEVKLMU-FOWTUZBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.83
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  12.36
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  氢氰酸 、 (E)-N-(1-(naphthalen-2-yl)ethylidene)prop-2-en-1-amine 在 C₃₆H₅₂N₄O₅ 作用下， 以 甲苯 为溶剂， 反应 65.0h， 生成 、
  参考文献：
  名称：

  Enantioselective Catalytic Addition of HCN to Ketoimines. Catalytic Synthesis of Quaternary Amino Acids

  摘要：

  Highly enantioselective addition of HCN to ketoimines has been achieved for the first time using readily accessible and recyclable Schiff base catalysts. Essentially quantitative isolated yield and enantioselectivity of up to 95% ee was obtained. Furthermore, some of the Strecker adducts could be recrystallized in high recovery, yielding optically pure materials. Conversion of the alpha-aminonitrile adducts to the corresponding alpha-quaternary alpha-amino acids was effected in high yield by a formylation/hydrolysis sequence.

  DOI：

  10.1021/ol005636+
• 作为产物：
  描述：

  丙烯胺 、 2-萘乙酮 在 3 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 以70%的产率得到(E)-N-(1-(naphthalen-2-yl)ethylidene)prop-2-en-1-amine
  参考文献：
  名称：

  Enantioselective Catalytic Addition of HCN to Ketoimines. Catalytic Synthesis of Quaternary Amino Acids

  摘要：

  Highly enantioselective addition of HCN to ketoimines has been achieved for the first time using readily accessible and recyclable Schiff base catalysts. Essentially quantitative isolated yield and enantioselectivity of up to 95% ee was obtained. Furthermore, some of the Strecker adducts could be recrystallized in high recovery, yielding optically pure materials. Conversion of the alpha-aminonitrile adducts to the corresponding alpha-quaternary alpha-amino acids was effected in high yield by a formylation/hydrolysis sequence.

  DOI：

  10.1021/ol005636+

文献信息

• α-Palladation of Imines as Entry to Dehydrogenative Heck Reaction: Aerobic Oxidative Cyclization of <i>N</i>-Allylimines to Pyrroles
  作者：Zhiyuan Chen、Beili Lu、Zhenhua Ding、Ke Gao、Naohiko Yoshikai

  DOI：10.1021/ol400638q

  日期：2013.4.19

  here a palladium(II)-catalyzed oxidative cyclization reaction of N-allylimines derived from methyl ketones, typically acetophenones, affording pyrrole derivatives at room temperature under oxygen atmosphere. The reaction likely proceeds through α-palladation of the imine followed by olefin migratory insertion and β-hydride elimination, thus representing a new example of aerobic dehydrogenative Heck cyclization

  我们在这里报告钯（II）催化的N-烯丙胺衍生自甲基酮（通常为苯乙酮）的氧化环化反应，在室温下在氧气气氛下提供吡咯衍生物。该反应可能通过亚胺的α-palletation继之以烯烃迁移插入和β-氢化物消除而进行，因此代表了好氧脱氢Heck环化的新实例。