N1-(2-methyl-1-phenyl-3-butenyl)-4-methyl-1-benzenesulfonamide | 914111-95-8

• 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: N1-(2-methyl-1-phenyl-3-butenyl)-4-methyl-1-benzenesulfonamide
• 英文别名: 4-methyl-N-(2-methyl-1-phenylbut-3-enyl)benzenesulfonamide
• CAS: 914111-95-8
• 化学式: C₁₈H₂₁NO₂S
• 分子量: 315.436
• InChiKey: AZQMWXPUKQGRLI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N1-(2-methyl-1-phenyl-3-butenyl)-4-methyl-1-benzenesulfonamide 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成
  参考文献：
  名称：

  Syn diastereoselectivity in the synthesis of homoallylamine using crotylsilane in the three-component reaction

  摘要：

  Crotylsilane was used in a three-component reaction for the synthesis of homoallylamines from aldehydes. A moderate to good syn/anti 5/1 diastereoselectivity was observed. The obtained homoallylamines were transformed into pyrrolidines or piperidines. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02025-6
• 作为产物：
  描述：

  1-溴-2-丁烯 、 N-亚苄基-4-甲基苯磺酰胺 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 4 A molecular sieve 、 tin(ll) chloride 作用下， 以 二氯甲烷 为溶剂， 以76%的产率得到N1-(2-methyl-1-phenyl-3-butenyl)-4-methyl-1-benzenesulfonamide
  参考文献：
  名称：

  Pd0/SnII promoted Barbier-type allylation and crotylation of sulfonimines

  摘要：

  A one-pot Barbier protocol is described for the facile formation of homoallyl sulfonamides from sulfonimines and allyl or crotyl bromide in the presence of SnCl2, and catalytic Pd-2(dba)(3)center dot CHCl3 at room temperature. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.07.201

文献信息

• Allylation and highly diastereoselective syn or anti crotylation of N-toluenesulfonylimines using potassium allyl- and crotyltrifluoroborates
  作者：Sze-Wan Li、Robert A. Batey

  DOI：10.1039/b403759f

  日期：——

  Air and moisture stable potassium allyl- and crotyltrifluoroborates undergo addition to N-sulfonyl and N-sulfinyl aldimines in the presence of Lewis acids, to provide the corresponding homoallylic amines in high yields and excellent diastereoselectivity.

  稳定于空气和湿气的氯化铝钾和氟化铝钾在路易斯酸的存在下与N-磺酰和N-亚磺酰醛胺发生加成反应，生成相应的同戊基胺，产率高且立体选择性优异。
• Palladium-catalyzed asymmetric umpolung allylation of imines with allylic alcohols
  作者：Xiang-Chen Qiao、Shou-Fei Zhu、Wang-Qiao Chen、Qi-Lin Zhou

  DOI：10.1016/j.tetasy.2010.03.003

  日期：2010.5

  A palladium-catalyzed asymmetric umpolung allylation reaction of imines with allylic alcohols has been developed. In the presence of chiral spiro phosphoramidite ligand 4, the allylation was accomplished with high yields and good enantioselectivities. The use of highly stable and easily available allylic alcohols instead of allylic metal reagents facilitated the preparation of chiral homoallylic amines

  已开发出钯催化的亚胺与烯丙醇的不对称聚烯丙基烯丙基化反应。在手性螺亚磷酰胺配体4的存在下，烯丙基化以高收率和良好的对映选择性完成。使用高度稳定且易于获得的烯丙基醇代替烯丙基金属试剂有助于制备手性均烯丙基胺。
• Regio- and Stereoselective Palladium-Pincer Complex Catalyzed Allylation of Sulfonylimines with Trifluoro(allyl)borates and Allylstannanes: A Combined Experimental and Theoretical Study
  作者：Olov A. Wallner、Kálmán J. Szabó

  DOI：10.1002/chem.200600406

  日期：2006.9.6

  employed as allylic precursors; however, the reaction with trifluoro(crotyl)borate results in poor stereoselectivity. The major diastereomer formed in these reactions was the syn isomer, while the (previously reported) reactions with aldehyde electrophiles afforded the anti products, indicating that the mechanism of the stereoselection is dependent on the applied electrophile. Therefore, we have studied

  已经通过使用取代的三氟（烯丙基）硼酸酯和三甲基烯丙基锡烷来进行区域和立体选择性的钯-钳子络合物催化磺酰亚胺的烯丙基化。反应为相应的支链烯丙基产物提供了极好的区域选择性。当使用三氟（肉桂基）硼酸酯和三甲基肉桂基锡烷作为烯丙基前体时，这些方法的立体选择性很高。然而，与三氟（巴豆基）硼酸酯的反应导致差的立体选择性。在这些反应中形成的主要非对映异构体是顺式异构体，而与醛亲电试剂的反应（先前报道）提供了反产物，表明立体选择的机理取决于所施加的亲电试剂。所以，我们通过实验研究和DFT建模研究了烯丙基化反应的机理。实验机理研究清楚地表明，三氟（烯丙基）硼酸钾与钯-钳子配合物1a发生金属转移，从而得到eta（1）-烯丙基钯-钳子配合物（1 e）。在理论上以B3PW91 / LANL2DZ + P的水平通过DFT计算研究了烯丙基部分从钯向磺酰亚胺碱底物转移的机理。这些计算表明，磺酰亚胺的亲电取代是在一步法中