N-(3,5-dichloro-1-pyridylidene)-4-methyl-benzenesulfonamide | 1274906-14-7

• 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-(3,5-dichloro-1-pyridylidene)-4-methyl-benzenesulfonamide
• 英文别名: (3,5-dichloropyridinium-1-yl)tosylamide；(3,5-Dichloropyridin-1-ium-1-yl)-(4-methylphenyl)sulfonylazanide
• CAS: 1274906-14-7
• 化学式: C₁₂H₁₀Cl₂N₂O₂S
• 分子量: 317.196
• InChiKey: HGUPYZNAMWRULE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  47.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(3,5-dichloro-1-pyridylidene)-4-methyl-benzenesulfonamide 在 [1,3-bis(diisopropylphenyl)imidazol-2-ylidene]AuNTf₂ 、 双三氟甲烷磺酰亚胺银盐 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 3.5h， 生成 N-(6-fluoro-3,3-dimethyl-1-phenyl-3,3a-dihydro-1H-indeno[1,2-c]furan-8(8aH)-ylidene)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  银催化的环丙基-茚满胺与羰基化合物的立体选择性[3 + 2]环加成反应

  摘要：

  据报道，在单取代的环丙基-茚满胺和醛之间存在银催化的立体选择性[3 + 2]环加成反应。反应的立体化学过程通过循环过渡态得以合理化。除非外部的醛与银催化剂一起存在，否则所得的茚满胺环加合物不容易水解。明显地，该水解过程导致所得茚满酮产物的立体化学改变。

  DOI：

  10.1002/adsc.201300090
• 作为产物：
  描述：

  、 对甲苯磺酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以80%的产率得到N-(3,5-dichloro-1-pyridylidene)-4-methyl-benzenesulfonamide
  参考文献：
  名称：

  Gold-Catalyzed Nitrene Transfer to Activated Alkynes: Formation of α,β-Unsaturated Amidines

  摘要：

  A gold-catalyzed intermolecular nitrene transfer to alkynes was developed for the first time, revealing a new mode of nitrene transfer and providing a novel access to versatile alpha-imino metal carbenes. Various mild nitrene-transfer reagents were examined, and iminopyridium ylides especially those based on 3,5-dichloropyridine proved be highly effective. With activated alkynes such as N-alkynyloxazolidinones as substrates, alpha,beta-unsaturated amidines were formed in mostly good yields.

  DOI：

  10.1021/ol2002607

文献信息

• Oxidant-Dependent Chemoselectivity in the Gold-Catalyzed Oxidative Cyclizations of 3,4,6,6-Tetrasubstituted 3,5-Dien-1-ynes
  作者：Hsiao-Hua Hung、Yi-Ching Liao、Rai-Shung Liu

  DOI：10.1021/jo401161h

  日期：2013.8.16

  chemoselectivity in the gold-catalyzed oxidative cyclization of 3,5-dien-1-ynes was observed when 3,5-dichloropyridine N-oxide replaced 8-methylquinoline N-oxide as the oxidant; the resulting cyclopentadienyl aldehydes were obtained in good yields. The altered chemoselectivity is attributed to a prior enyne cyclization in the presence of 3,5-dichloropyridine N-oxides. The use of N-iminopyridium ylide

  当3,5-二氯吡啶N-氧化物代替8-甲基喹啉N-氧化物作为氧化剂时，在金催化的3,5-dien-1-ynes的氧化环化中具有明显的化学选择性。得到的环戊二烯基醛的收率很高。改变的化学选择性归因于在3，5-二氯吡啶N-氧化物存在下先前的炔烃环化。N-亚氨基吡啶鎓叶立德的使用使得类似的亚氨基环化反应能够有效地产生环戊二烯基亚胺。我们的实验数据支持先前的3,5-dien-1-ynes的金催化环化反应生成金卡宾，然后用N-氧化物氧化。
• Gold-Catalyzed Nitrene Transfer to Activated Alkynes: Formation of α,β-Unsaturated Amidines
  作者：Chaoqun Li、Liming Zhang

  DOI：10.1021/ol2002607

  日期：2011.4.1

  A gold-catalyzed intermolecular nitrene transfer to alkynes was developed for the first time, revealing a new mode of nitrene transfer and providing a novel access to versatile alpha-imino metal carbenes. Various mild nitrene-transfer reagents were examined, and iminopyridium ylides especially those based on 3,5-dichloropyridine proved be highly effective. With activated alkynes such as N-alkynyloxazolidinones as substrates, alpha,beta-unsaturated amidines were formed in mostly good yields.
• Silver-Catalyzed Stereoselective [3+2] Cycloadditions of Cyclopropyl-Indanimines with Carbonyl Compounds
  作者：Hsiao-Hua Hung、Yi-Ching Liao、Rai-Shung Liu

  DOI：10.1002/adsc.201300090

  日期：2013.5.17

  Silver‐catalyzed stereoselective [3+2] cycloadditions between mono‐substituted cyclopropyl‐indanimines and aldehydes are reported. The stereochemical course of the reaction is rationalized with a cyclic transition state. The resulting indanimine cycloadducts are not readily hydrolyzed unless external aldehydes are present with the silver catalyst. Notably, this hydrolysis process leads to a change

  据报道，在单取代的环丙基-茚满胺和醛之间存在银催化的立体选择性[3 + 2]环加成反应。反应的立体化学过程通过循环过渡态得以合理化。除非外部的醛与银催化剂一起存在，否则所得的茚满胺环加合物不容易水解。明显地，该水解过程导致所得茚满酮产物的立体化学改变。