N-allyl-N-[2-(allylthio)phenyl]-4-methylbenzenesulfonamide | 820975-73-3

• 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-allyl-N-[2-(allylthio)phenyl]-4-methylbenzenesulfonamide
• 英文别名: 4-methyl-N-prop-2-enyl-N-(2-prop-2-enylsulfanylphenyl)benzenesulfonamide
• CAS: 820975-73-3
• 化学式: C₁₉H₂₁NO₂S₂
• 分子量: 359.513
• InChiKey: BQXVESDSYPFFNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-allyl-N-[2-(allylthio)phenyl]-4-methylbenzenesulfonamide 在 Grubbs' second generation catalyst C₃₀H₅₀Cl₂N₂O₄PS₂Ru 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 96.0h， 生成 6-[(4-methylphenyl)sulfonyl]-5,6-dihydro-2H-1,6-benzothiazocine 1,1-dioxide
  参考文献：
  名称：

  Isomerization and ring-closing metathesis for the synthesis of 6-, 7- and 8-membered benzo- and pyrido-fused N,N-, N,O- and N,S-heterocycles

  摘要：

  An isomerization-ring-closing metathesis (RCM) strategy afforded N-substituted 4H-1,4-benzoxazines from the protected N-allyl-2-(allyloxy)anilines. In addition, RCM was used to synthesize the N-substituted, 8-membered benzo-fused heterocycles from the respective diallyl compounds: 1,2,5,6-tetraliydro-1,6-benzodiazocine, 5,6-dihydro-2H-1,6-benzoxazocine, 5,6,9, 10-tetrahydropyrido[2,3-b][1,4]diazocine and 5,6-dihydro-2H-1,6-benzothiazocine 1,1-dioxide. The isomerization-RCM approach also afforded the 7-membered ring system, 2,5-diliydro-1,5-benzothiazepine 1,1-dioxide, from the protected N-allyl-2-(allylsulfonyl)aniline. Furthermore, the structure of 1,6-bis[(4-methylplienyl)sulfonyl]-1,2,5,6-tetrahydro-1,6-benzodiazocine was confirmed by a single crystal X-ray determination. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.10.108
• 作为产物：
  描述：

  2-丙-2-烯基硫基苯胺 在 吡啶 、 potassium carbonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 48.0h， 生成 N-allyl-N-[2-(allylthio)phenyl]-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Isomerization and ring-closing metathesis for the synthesis of 6-, 7- and 8-membered benzo- and pyrido-fused N,N-, N,O- and N,S-heterocycles

  摘要：

  An isomerization-ring-closing metathesis (RCM) strategy afforded N-substituted 4H-1,4-benzoxazines from the protected N-allyl-2-(allyloxy)anilines. In addition, RCM was used to synthesize the N-substituted, 8-membered benzo-fused heterocycles from the respective diallyl compounds: 1,2,5,6-tetraliydro-1,6-benzodiazocine, 5,6-dihydro-2H-1,6-benzoxazocine, 5,6,9, 10-tetrahydropyrido[2,3-b][1,4]diazocine and 5,6-dihydro-2H-1,6-benzothiazocine 1,1-dioxide. The isomerization-RCM approach also afforded the 7-membered ring system, 2,5-diliydro-1,5-benzothiazepine 1,1-dioxide, from the protected N-allyl-2-(allylsulfonyl)aniline. Furthermore, the structure of 1,6-bis[(4-methylplienyl)sulfonyl]-1,2,5,6-tetrahydro-1,6-benzodiazocine was confirmed by a single crystal X-ray determination. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.10.108

文献信息

• Application of an isomerization-ring-closing metathesis strategy to the synthesis of unsaturated seven-membered, benzo-fused heterocycles containing two heteroatoms
  作者：Dharmendra B. Yadav、Garreth L. Morgans、Blessing A. Aderibigbe、Lee G. Madeley、Manuel A. Fernandes、Joseph P. Michael、Charles B. de Koning、Willem A.L. van Otterlo

  DOI：10.1016/j.tet.2011.02.035

  日期：2011.4

  An isomerization-RCM approach was utilized to synthesize a number of seven-membered benzo-fused heterocycles containing two heteroatoms (N,O, N,S, and S,O). This approach utilized the ruthenium catalyst [RuClH(CO)(PPh3)3] for the isomerization of allyl groups, eventually followed by the use of the Grubbs second generation catalyst for the formation of the desired products. In most instances thermal

  利用异构化-RCM方法合成了许多含有两个杂原子（N，O，N，S和S，O）的七元苯并稠合杂环。该方法利用了钌催化剂[RuClH（CO）（PPh 3）3进行烯丙基的异构化，最后使用Grubbs第二代催化剂形成所需的产物。在大多数情况下，热RCM条件就足够了；然而，在许多情况下，该方法不能使所需的产品具有高温，短时间的微波方法可以提供所需的闭环产品。以这种方式，成功地合成了以下取代的苯并稠合的支架：4,5-二氢-1,5-苯并x氮平，4,5-和2,5-二氢-1,5-苯并噻氮平和2 H -1,5 -苯并沙地平。
• Formation of an unexpected rearrangement product using Grubbs’ second generation catalyst: 2-allyl-3,4-dihydro-2H-1,4-benzothiazines from diene precursors
  作者：Garreth L. Morgans、Dharmendra B. Yadav、Manuel A. Fernandes、Charles B. de Koning、Joseph P. Michael、Willem A.L. van Otterlo

  DOI：10.1016/j.tetlet.2012.02.109

  日期：2012.5

  6-dihydro-2H-1,6-benzothiazocine, as well as the unexpected 2-allyl-4-[(4-methylphenyl)sulfonyl]-3,4-dihydro-2H-1,4-benzothiazine. Use of similar conditions on an analogous sulfoxide resulted in the expected product, 6-[(4-methylphenyl)sulfonyl]-5,6-dihydro-2H-1,6-benzothiazocine 1-oxide, indicating that the sulfide was playing a key role in this novel transformation. Furthermore, the use of N-allyl-4-methyl-

  将亚化学计量的Grubbs第二代催化剂应用于底物N-烯丙基-N- [2-（烯丙基硫烷基）苯基] -4-甲基苯磺酰胺，得到闭环化合物6-[（4-甲基苯基）磺酰基]- 5,6-二氢-2 H -1,6-苯并噻唑啉，以及意想不到的2-烯丙基-4-[（4-甲基苯基）磺酰基] -3,4-二氢-2 H -1,4-苯并噻嗪。在类似的亚砜上使用相似的条件，得到了预期的产物6-[[（4-甲基苯基）磺酰基] -5,6-二氢-2 H -1,6-苯并噻唑啉-1-氧化物，表明该硫化物正在发挥在这种新颖转变中的关键作用。此外，使用N-烯丙基-4-甲基-N-2-[（（2-甲基-2-丙烯基）硫烷基]苯基}-苯磺酰胺在相同反应中得到2-（2-甲基-2-丙烯基）-3,4-二氢-2 H -1,4-苯并噻嗪。
• Synthesis of unsaturated 1,4-heteroatom-containing benzo-fused heterocycles using a sequential isomerization–ring-closing metathesis strategy
  作者：Garreth L. Morgans、E. Lindani Ngidi、Lee G. Madeley、Setshaba D. Khanye、Joseph P. Michael、Charles B. de Koning、Willem A.L. van Otterlo

  DOI：10.1016/j.tet.2009.10.061

  日期：2009.12

  A small library of 1,4-benzodioxins and 4H-1,4-benzoxazines was synthesized from the corresponding bis-allyloxy precursors by way of an initial isomerization to the bis-vinyloxy compounds, followed by a ring-closing metathesis using the second generation Grubbs' catalyst (G2). A related strategy, starting from benzene-1,2-dithiol and 2-mercaptophenol, afforded benzodithiin and 1,4-benzoxathiin, respectively. (C) 2009 Elsevier Ltd. All rights reserved.