1-[1-(Dimethylsulfamoylamino)but-3-enyl]-4-methoxybenzene | 1153630-44-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-[1-(Dimethylsulfamoylamino)but-3-enyl]-4-methoxybenzene
• CAS: 1153630-44-4
• 化学式: C₁₃H₂₀N₂O₃S
• 分子量: 284.379
• InChiKey: VMSBJBPBWNLEPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  67
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-[1-(Dimethylsulfamoylamino)but-3-enyl]-4-methoxybenzene 在 1,3-丙二胺 作用下， 反应 2.0h， 以90%的产率得到1-(4-methoxyphenyl)but-3-en-1-amine
  参考文献：
  名称：

  铟介导的 Barbier 型烯丙基化结合酶动力学拆分合成对映纯苄基高烯丙胺：走向含氮杂环的化学酶法合成

  摘要：

  Barbier 型铟介导的不同 N,N-(二甲基氨磺酰基)-保护的醛亚胺与许多烯丙基溴的烯丙基化，然后进行高产率脱保护，以良好到极好的产率提供烯丙胺。然后对外消旋胺进行酶动力学拆分以获得相应的(S)-胺和(R)-酰胺。当具有末端双键的酰基供体应用于酶动力学拆分时，产物酰胺可以通过闭环复分解以直接的方式转化为不饱和内酰胺。此外，对映体纯的 (S)-1-苯基丁-3-烯胺被转化为相应的二烯丙胺，然后进行闭环复分解以产生模拟许多天然产物的取代脱氢哌啶。

  DOI：

  10.1002/ejoc.200901216
• 作为产物：
  描述：

  N,N-dimethyl-N'-[(4-methoxyphenyl)methylene]sulfamide 、 烯丙基三丁基锡 在 resorcinolbis[(diphenyl)phosphinite] palladium trifluoroacetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以60%的产率得到1-[1-(Dimethylsulfamoylamino)but-3-enyl]-4-methoxybenzene
  参考文献：
  名称：

  P′CP′-Pincer palladium complex-catalyzed allylation of N,N-dimethylsulfamoyl-protected aldimines

  摘要：

  The P'CP'-pincer palladium complex-catalyzed allylation of N,N-dimethylsulfamoyl-protected aldimines with allyl(tributyl)stannane is investigated for the preparation of N-homoallylic sulfamides. The desired N,N-dimethylsulfamoyl-protected products are obtained in moderate to high yields in DMF under very mild conditions and a high yielding and convenient deprotection of the N,N-dimethylsulfamoyl group is also demonstrated. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.02.187

文献信息

• Synthesis of Enantiopure Benzyl Homoallylamines by Indium-Mediated Barbier-Type Allylation Combined with Enzymatic Kinetic Resolution: Towards the Chemoenzymatic Synthesis of N-Containing Heterocycles
  作者：Ari Hietanen、Tiina Saloranta、Sara Rosenberg、Evelina Laitinen、Reko Leino、Liisa T. Kanerva

  DOI：10.1002/ejoc.200901216

  日期：2010.2

  N-(dimethylsulfamoyl)-protected aldimines with a number of allyl bromides followed by high-yielding deprotection afforded allylic amines in good to excellent yields. The racemic amines were then subjected to enzymatic kinetic resolution in order to obtain the corresponding (S)-amines and (R)-amides. When acyl donors with a terminal double bond were applied in the enzymatic kinetic resolution, the product amide

  Barbier 型铟介导的不同 N,N-(二甲基氨磺酰基)-保护的醛亚胺与许多烯丙基溴的烯丙基化，然后进行高产率脱保护，以良好到极好的产率提供烯丙胺。然后对外消旋胺进行酶动力学拆分以获得相应的(S)-胺和(R)-酰胺。当具有末端双键的酰基供体应用于酶动力学拆分时，产物酰胺可以通过闭环复分解以直接的方式转化为不饱和内酰胺。此外，对映体纯的 (S)-1-苯基丁-3-烯胺被转化为相应的二烯丙胺，然后进行闭环复分解以产生模拟许多天然产物的取代脱氢哌啶。
• P′CP′-Pincer palladium complex-catalyzed allylation of N,N-dimethylsulfamoyl-protected aldimines
  作者：Jie Li、Adriaan J. Minnaard、Robertus J.M. Klein Gebbink、Gerard van Koten

  DOI：10.1016/j.tetlet.2009.02.187

  日期：2009.5

  The P'CP'-pincer palladium complex-catalyzed allylation of N,N-dimethylsulfamoyl-protected aldimines with allyl(tributyl)stannane is investigated for the preparation of N-homoallylic sulfamides. The desired N,N-dimethylsulfamoyl-protected products are obtained in moderate to high yields in DMF under very mild conditions and a high yielding and convenient deprotection of the N,N-dimethylsulfamoyl group is also demonstrated. (C) 2009 Elsevier Ltd. All rights reserved.