N-benzyloxycarbonyl-1-(3-chlorophenyl)but-3-enylamine

• 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-benzyloxycarbonyl-1-(3-chlorophenyl)but-3-enylamine
• 英文别名: benzyl N-[1-(3-chlorophenyl)but-3-enyl]carbamate
• 化学式: C₁₈H₁₈ClNO₂
• 分子量: 315.799
• InChiKey: GTOUYIKEPBHCMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  benzyl ((3-chlorophenyl)(tosyl)methyl)carbamate 、 烯丙基三甲基硅烷 在 indium(III) triflate 作用下， 以 二氯甲烷 为溶剂， 反应 9.0h， 以87%的产率得到N-benzyloxycarbonyl-1-(3-chlorophenyl)but-3-enylamine
  参考文献：
  名称：

  三氟甲磺酸铟催化N-磺酰基醛亚胺或N-烷氧基羰基氨基对甲苯砜与烯丙基三甲基硅烷的烯丙基化反应：受保护的均烯丙基胺的合成

  摘要：

  已经成功开发了N-磺酰基醛亚胺或N-烷氧基氧羰基氨基对甲苯砜与烯丙基三甲基硅烷的三氟甲磺酸铟催化的烯丙基化反应，以生产受保护的均烯丙基胺。

  DOI：

  10.1016/j.tet.2010.09.038

文献信息

• Magnesium Bistrifluoromethanesulfonimide Catalysed Three-Component Synthesis of Protected Homoallylic Amines
  作者：Hongshe Wang、Weixing Zhao

  DOI：10.3184/174751911x13056175312712

  日期：2011.5

  A one-pot, three-component reaction of an aldehyde, benzyl carbamate and allyltrimethylsilane in the presence of 3 mol% of magnesium bistrifluoromethanesulfonimide at room temperature has been shown to afford the corresponding protected homoallylic amine in high yield.

  在室温下在 3 mol% 双三氟甲磺酰亚胺镁存在下，醛、氨基甲酸苄酯和烯丙基三甲基硅烷的一锅三组分反应已被证明可以高产率地提供相应的受保护的高烯丙基胺。
• Magnesium Bistrifluoromethanesulfonimide Catalyzed Three-component Synthesis of Protected Homoallylic Amines
  作者：Hongshe Wang、June Zeng

  DOI：10.5012/bkcs.2011.32.7.2203

  日期：2011.7.20

  A mild and efficient procedure has been developed for the one-pot, three-component reaction of aldehydes, benzyl carbamate and allyltrimethylsilane in the presence of 3 mol % of magnesium bistrifluoromethanesulfonimide at room temperature to afford the corresponding protected homoallylic amines in high yields.

  已经开发了一种温和有效的方法，用于醛、氨基甲酸苄酯和烯丙基三甲基硅烷在室温下在 3 mol% 双三氟甲磺酰亚胺镁存在下的一锅三组分反应，以高收率提供相应的受保护的均烯丙基胺。
• Iodine as a Very Powerful Catalyst for Three-Component Synthesis of Protected Homoallylic Amines
  作者：Prodeep Phukan

  DOI：10.1021/jo0498462

  日期：2004.5.1

  Iodine catalyzes efficiently the three-component condensation of aldehydes, benzyl carbamate, and allyltrimethylsilane to afford the corresponding protected homoallylic amines in excellent yields.

  碘有效地催化醛，氨基甲酸苄酯和烯丙基三甲基硅烷的三组分缩合，以优异的产率提供相应的受保护的均烯丙基胺。
• Mild and Efficient Tris(pentafluorophenyl)borane-catalyzed Sakurai Allylation of N-Benzyloxycarbonylamino p-Tolylsulfone with Allyltrimethylsilane
  作者：Ponnaboina Thirupathi、Lok Nath Neupane、Keun-Hyeung Lee

  DOI：10.5012/bkcs.2012.33.4.1275

  日期：2012.4.20

  Tris(pentafluorophenyl)borane, $B(C_6F_5)_3$, was found to be an efficient catalyst for synthesis of N-Cbzhomoallylic amines using Sakurai allylation of N-benzyloxycarbonyl-amino p-tolylsulfones with allyltrimethylsilane.

  研究发现，三(五氟苯基)硼烷（$B(C_6F_5)_3$）是一种高效催化剂，可利用烯丙基三甲基硅烷对 N-苄氧羰基氨基对甲苯磺酸进行樱井烯丙基化，从而合成 N-苄基烯丙基胺。
• HBF4·OEt2: An efficient fluorinated acid catalyst for the one-pot synthesis of secondary and tertiary N-homoallylic carbamates
  作者：Gakul Baishya、Nabajyoti Hazarika、Barnali Sarmah

  DOI：10.1016/j.jfluchem.2014.06.028

  日期：2014.10

  An efficient method for the one-pot synthesis of secondary and tertiary N-homoallylic carbamates using catalytic amount of HBF4 center dot OEt2 is described. The reaction proceeded smoothly to afford the corresponding N-homoallylic carbamates in good to high yields. Operationally simple and easily scalable features make this method more practical over existing methods. Use of HBF4 center dot OEt2 as an acid catalyst also proves the catalytic activity of fluorinated acid catalyst in this important organic transformation. (C) 2014 Elsevier B.V. All rights reserved.