N-(3-phenylcyclohex-2-enyl)acetamide | 83277-95-6

• 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: N-(3-phenylcyclohex-2-enyl)acetamide
• 英文别名: N-(3-phenylcyclohex-2-en-1-yl)acetamide
• CAS: 83277-95-6
• 化学式: C₁₄H₁₇NO
• 分子量: 215.295
• InChiKey: CKKVALLBUQWEMT-UHFFFAOYSA-N

物化性质

• 熔点：
  118 °C
• 沸点：
  409.7±45.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  5,6-二氢-[1,1’-联苯]-3(4H)-酮 在 titanium(IV) isopropylate 、 Rh((R)-binaphane)(COD)BF4 、 氨 、 氢气 作用下， 以 甲醇 、 甲苯 为溶剂， 5.0~55.0 ℃ 、101.33 kPa 条件下， 反应 44.25h， 生成 N-(3-phenylcyclohex-2-enyl)acetamide
  参考文献：
  名称：

  Rh催化的不对称加氢反应高度手性合成手性环状烯丙基胺

  摘要：

  已经开发了由Rh-DuanPhos配合物催化的环状二烯酰胺的高度区域选择性和对映选择性不对称氢化反应，它为合成手性环状烯丙基胺具有出色的对映选择性（高达99％ee）提供了一种容易获得的方法。该产品是有价值的手性结构单元，可以轻松转化为多取代的环己烷衍生物。

  DOI：

  10.1021/ol501421g

文献信息

• Chemoselectivity in Coupling of Azides with Thioacids in Solution-Phase and Solvent-Free Conditions
  作者：Sangaraiah Nagarajan、Poovan Shanmugavelan、Murugan Sathishkumar、Namachivayam Priyadharshini、Padmanaban Sudakar、Alagusundaram Ponnuswamy

  DOI：10.1080/00397911.2011.606043

  日期：2013.1.1

  Solvent-free rapid coupling of monothiocarboxylic acid with azide affords carboxamide chemoselectively. Triphenyl phosphine included as an additive influences the chemoselectivity, yielding carboxamide and thioamide. Similar variation in the chemoselectivity is observed in the absence and presence of triphenyl phosphine in solution-phase methodology. Rapidity and ecofriendliness of the solvent-free approach to yield the products in just 15 min is noteworthy compared to the solution-phase protocol, which has a long reaction time (1-3 days).
• Murugan, Sathish Kumar; Sangaraiah, Nagarajan; Velan, Poovan Shanmuga, Journal of the Brazilian Chemical Society, 2011, vol. 22, # 11, p. 2065 - 2069
  作者：Murugan, Sathish Kumar、Sangaraiah, Nagarajan、Velan, Poovan Shanmuga、Murugan, Dinesh、Ponnuswamy, Alagusundaram

  DOI：——

  日期：——
• Solvent-free protocol for amide bond formation via trapping of nascent phosphazenes with carboxylic acids
  作者：Murugan Sathishkumar、Poovan Shanmugavelan、Sangaraiah Nagarajan、Murugesan Maheswari、Murugan Dinesh、Alagusundaram Ponnuswamy

  DOI：10.1016/j.tetlet.2011.03.069

  日期：2011.6

  A solvent-free synthesis of amides via the coupling of phosphazenes with carboxylic acids is reported. Increasing the rate of heating either by microwave irradiation or conventional heating results in multifold increase in the rate of amide bond formation. Synthesis of a library of amides including a potent antitumour candidate has been accomplished. (C) 2011 Elsevier Ltd. All rights reserved.
• Highly Enantioselective Synthesis of Chiral Cyclic Allylic Amines via Rh-Catalyzed Asymmetric Hydrogenation
  作者：Ming Zhou、Tang-Lin Liu、Min Cao、Zejian Xue、Hui Lv、Xumu Zhang

  DOI：10.1021/ol501421g

  日期：2014.7.3

  enantioselective asymmetric hydrogenation of cyclic dienamides catalyzed by an Rh-DuanPhos complex has been developed, which provides a readily accessible method for the synthesis of chiral cyclic allylic amines in excellent enantioselectivities (up to 99% ee). The products are valuable chiral building blocks and could be easily transformed to multisubstituted cyclohexane derivatives.

  已经开发了由Rh-DuanPhos配合物催化的环状二烯酰胺的高度区域选择性和对映选择性不对称氢化反应，它为合成手性环状烯丙基胺具有出色的对映选择性（高达99％ee）提供了一种容易获得的方法。该产品是有价值的手性结构单元，可以轻松转化为多取代的环己烷衍生物。