N-((E)-3-cyclohexyl-2-propenyl)aniline | 373362-49-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-((E)-3-cyclohexyl-2-propenyl)aniline
• 英文别名: (E)-N-(3-cyclohexylallyl)benzenamine；N-[(E)-3-cyclohexylprop-2-enyl]aniline
• CAS: 373362-49-3
• 化学式: C₁₅H₂₁N
• 分子量: 215.338
• InChiKey: WDILJTGVLQVAGO-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  环己基丙二醇 、 苯胺 在 gold(III) bromide 作用下， 以 四氢呋喃 为溶剂， 以75%的产率得到N-((E)-3-cyclohexyl-2-propenyl)aniline
  参考文献：
  名称：

  金与芳基胺的丙二烯分子间加氢胺化反应和高手性转移。

  摘要：

  DOI：

  10.1002/anie.200600331

文献信息

• Sulfoxide ligand metal catalyzed oxidation of olefins
  申请人：The Board of Trustees of the University of Illinois

  公开号：US10266503B1

  公开（公告）日：2019-04-23

  The enantioselective synthesis of isochroman motifs has been accomplished via Pd(II)-catalyzed allylic C—H oxidation from terminal olefin precursors. Critical to the success of this goal was the development and utilization of a novel chiral aryl sulfoxide-oxazoline (ArSOX) ligand. The allylic C—H oxidation reaction proceeds with the broadest scope and highest levels asymmetric induction reported to date (avg. 92% ee, 13 examples ≥90% ee). Additionally, C(sp3)-N fragment coupling reaction between abundant terminal olefins and N-triflyl protected aliphatic and aromatic amines via Pd(II)/sulfoxide (SOX) catalyzed intermolecular allylic C—H amination is disclosed. A range of 52 allylic amines are furnished in good yields (avg. 76%) and excellent regio- and stereoselectivity (avg. >20:1 linear:branched, >20:1 E:Z). For the first time, a variety of singly activated aromatic and aliphatic nitrogen nucleophiles, including ones with stereochemical elements, can be used in fragment coupling stiochiometries for intermolecular C—H amination reactions.

  通过Pd(II)-催化的烯烃末端前体的烯丙基C—H氧化，已经实现了对异色烷基苯并环的对映选择性合成。这一目标的成功关键在于开发和利用一种新型手性芳基亚砜-噁唑啉（ArSOX）配体。烯丙基C—H氧化反应具有迄今报道的最广泛范围和最高水平的不对称诱导（平均92% ee，13个例子≥90% ee）。此外，通过Pd(II)/亚砜（SOX）催化的分子间烯丙基C—H胺化揭示了丰富的末端烯烃和N-三氟甲磺酰保护的脂肪族和芳香族胺之间的C(sp3)-N片段偶联反应。一系列52种烯丙基胺以良好的产率（平均76%）和优异的区域和立体选择性（平均>20:1线性:支链，>20:1 E:Z）提供。首次，各种单独活化的芳香族和脂肪族氮亲核试剂，包括具有立体化学元素的试剂，可以在分子间C—H胺化反应的片段偶联化学计量中使用。
• Iridium Complex-Catalyzed Allylic Amination of Allylic Esters
  作者：Ryo Takeuchi、Naoki Ue、Keisuke Tanabe、Kengo Yamashita、Norihito Shiga

  DOI：10.1021/ja0112036

  日期：2001.10.1

  Iridium complex-catalyzed allylic amination of allylic carbonates was studied. The solvent strongly affected the catalytic activity. The use of a polar solvent such as EtOH is essential for obtaining the products in high yield, The reaction of (E)-3-substituted-2-propenyl carbonate and 1-substituted-2-propenyl carbonate with pyrrolidine in the presence of a catalytic amount of [Ir(COD)Cl](2) and P(OPh)(3) (P/Ir = 2) gave a branch amine with up to 99% selectivity. Both secondary and primary amines could be used for this reaction. When a primary amine was used, selective monoallylation occurred. No diallylation product was obtained. The reaction of 1,1-disubstituted-2 propenyl acetate with amines exclusively gave an alpha,alpha -disubstituted allylic amine. This reaction provides an alternative route to the addition of an organometallic reagent to ketimines. for the preparation of such amines. The reaction of (Z)-3-substituted-2-propenyl carbonate with amines gave (Z)-linear amines with up to 100% selectivity. In all cases, no (E)-linear amine was obtained. The selectivities described here have not been achieved in similar palladium complex-catalyzed reactions.
• Gold-Catalyzed Intermolecular Hydroamination of Allenes with Arylamines and Resulting High Chirality Transfer
  作者：Naoko Nishina、Yoshinori Yamamoto

  DOI：10.1002/anie.200600331

  日期：2006.5.12