N-((S)-2-Hydroxy-1-phenyl-2-vinyl-but-3-enyl)-4-methyl-benzenesulfonamide | 335150-99-7

• 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-((S)-2-Hydroxy-1-phenyl-2-vinyl-but-3-enyl)-4-methyl-benzenesulfonamide
• 英文别名: N-[(1S)-2-ethenyl-2-hydroxy-1-phenylbut-3-enyl]-4-methylbenzenesulfonamide
• CAS: 335150-99-7
• 化学式: C₁₉H₂₁NO₃S
• 分子量: 343.447
• InChiKey: ITAQPHUMHWEGHW-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  74.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-((S)-2-Hydroxy-1-phenyl-2-vinyl-but-3-enyl)-4-methyl-benzenesulfonamide 在 N,N-二甲基丙烯基脲 、 (bis(tricyclohexyl)phosphine)ruthenium(II) dichloride 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 (2S,3S)-3-Allyloxy-2-phenyl-1-(toluene-4-sulfonyl)-3-vinyl-1,2,3,6-tetrahydro-pyridine
  参考文献：
  名称：

  A Double Ring Closing Metathesis Reaction in the Rapid, Enantioselective Synthesis of NK-1 Receptor Antagonists

  摘要：

  [GRAPHICS]The NK-1 receptor antagonist 1 has been prepared in seven steps from phenylglycine methyl ester. The key steps are a double ring closing metathesis reaction of tetraene 7 to prepare spirocycle 6 and a reductive Heck reaction to introduce the aryl moiety. This latter reaction discriminates the olefins of compound 6 and proceeds in a highly regio- and stereoselective manner.

  DOI：

  10.1021/ol006958g
• 作为产物：
  描述：

  (S)-(+)-2-苯甘氨酸甲酯 盐酸盐 在 cerium(III) chloride 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 N-((S)-2-Hydroxy-1-phenyl-2-vinyl-but-3-enyl)-4-methyl-benzenesulfonamide
  参考文献：
  名称：

  A Double Ring Closing Metathesis Reaction in the Rapid, Enantioselective Synthesis of NK-1 Receptor Antagonists

  摘要：

  [GRAPHICS]The NK-1 receptor antagonist 1 has been prepared in seven steps from phenylglycine methyl ester. The key steps are a double ring closing metathesis reaction of tetraene 7 to prepare spirocycle 6 and a reductive Heck reaction to introduce the aryl moiety. This latter reaction discriminates the olefins of compound 6 and proceeds in a highly regio- and stereoselective manner.

  DOI：

  10.1021/ol006958g

文献信息

• Ring-Closing Metathesis Reactions of Bis(enynes): Selectivity and Surprises
  作者：Debra J. Wallace、Robert A. Reamer

  DOI：10.1021/jo500815q

  日期：2014.6.20

  A study of the ring-closing metathesis reactions of two bis(enynes) is presented. These substrates, which contain two alkenes and two alkynes, as well as a resident stereocenter, can potentially generate metathesis products resulting from many reaction pathways. In this contribution we present our results on these reactions, show how small changes in reaction conditions can lead to different product

  提出了两个双（烯炔）的闭环复分解反应的研究。这些包含两个烯烃和两个炔烃以及一个驻留的立体中心的底物可能潜在地产生由许多反应途径产生的复分解产物。在这项贡献中，我们介绍了这些反应的结果，显示了反应条件的微小变化会导致不同的产物比率，并试图为结果提供理论依据。
• A Double Ring Closing Metathesis Reaction in the Rapid, Enantioselective Synthesis of NK-1 Receptor Antagonists
  作者：Debra J. Wallace、Jonathan M. Goodman、Derek J. Kennedy、Antony J. Davies、Cameron J. Cowden、Michael S. Ashwood、Ian F. Cottrell、Ulf-H. Dolling、Paul J. Reider

  DOI：10.1021/ol006958g

  日期：2001.3.1

  [GRAPHICS]The NK-1 receptor antagonist 1 has been prepared in seven steps from phenylglycine methyl ester. The key steps are a double ring closing metathesis reaction of tetraene 7 to prepare spirocycle 6 and a reductive Heck reaction to introduce the aryl moiety. This latter reaction discriminates the olefins of compound 6 and proceeds in a highly regio- and stereoselective manner.