N-allyl-N-p-toluenesulfonyl-5-chloro-2-formylaniline | 675578-49-1

• 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-p-toluenesulfonyl-5-chloro-2-formylaniline
• CAS: 675578-49-1
• 化学式: C₁₇H₁₆ClNO₃S
• 分子量: 349.838
• InChiKey: LWSMYWCTYVVSNV-UHFFFAOYSA-N

物化性质

• 熔点：
  117-118 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  505.9±60.0 °C(Predicted)
• 密度：
  1.319±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.84
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  54.45
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-allyl-N-p-toluenesulfonyl-5-chloro-2-formylaniline 在 tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene](benzylidene)Ru(II) dichloride 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.25h， 生成 N-p-toluenesulfonyl-7-chloro-1,2-dihydroquinoline
  参考文献：
  名称：

  A novel synthesis of substituted quinolines using ring-closing metathesis (RCM): its application to the synthesis of key intermediates for anti-malarial agents

  摘要：

  A method for synthesizing substituted quinolines using ruthenium-catalyzed ring-closing metathesis as a key step has been developed. Substituted 1,2-dihydroquinolines, 4-silyloxy-1,2-dihydroquinoline and 4-methoxy-1,2-dihydroquinoline, were successfully synthesized in excellent yields via ene-ene metathesis and silyl or alkyl enol ether-ene metathesis, respectively. The synthetic intermediates of the antimalarial agents quinine, chloroquine, and PPMP-quinine hybrid were efficiently synthesized by this methodology. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.01.084
• 作为产物：
  描述：

  N-p-toluenesulfonyl-4-chloro-anthranilic acid methyl ester 在 manganese(IV) oxide 、 二异丁基氢化铝 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 、 苯 为溶剂， 反应 6.0h， 生成 N-allyl-N-p-toluenesulfonyl-5-chloro-2-formylaniline
  参考文献：
  名称：

  A novel synthesis of substituted quinolines using ring-closing metathesis (RCM): its application to the synthesis of key intermediates for anti-malarial agents

  摘要：

  A method for synthesizing substituted quinolines using ruthenium-catalyzed ring-closing metathesis as a key step has been developed. Substituted 1,2-dihydroquinolines, 4-silyloxy-1,2-dihydroquinoline and 4-methoxy-1,2-dihydroquinoline, were successfully synthesized in excellent yields via ene-ene metathesis and silyl or alkyl enol ether-ene metathesis, respectively. The synthetic intermediates of the antimalarial agents quinine, chloroquine, and PPMP-quinine hybrid were efficiently synthesized by this methodology. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.01.084

文献信息

• Pd-Catalyzed Migratory Cycloisomerization of <i>N</i>-Allyl-<i>o</i>-allenylaniline Derivatives
  作者：Yasuhiro Ii、Satoru Hirabayashi、Shohei Yoshioka、Hiroshi Aoyama、Kenichi Murai、Hiromichi Fujioka、Mitsuhiro Arisawa

  DOI：10.1021/acs.orglett.9b00676

  日期：2019.5.17

  The Pd-catalyzed migratory cycloisomerization of N-allyl-o-allenyl aniline derivatives is first reported to give indoles having a substituent at the 2-position.

  的Pd催化的洄游环异构Ñ -allyl- ö -allenyl苯胺衍生物是首次报道，得到具有在2-位的取代基的吲哚。
• Synthesis of substituted 1,2-dihydroquinolines and quinolines using ene–ene metathesis and ene–enol ether metathesis
  作者：Mitsuhiro Arisawa、Chumpol Theeraladanon、Atsushi Nishida、Masako Nakagawa

  DOI：10.1016/s0040-4039(01)01714-2

  日期：2001.11

  We describe a novel and convenient method for quinoline synthesis using ring-closing olefin metathesis (RCM), ene-ene metathesis, and ene-enol ether metathesis. We also report the first example of enol silyl ether-ene metathesis to produce cyclic enol silyl ether. Using this method, versatile substituted quinoline derivatives were readily prepared in excellent yield from anthranilic acid derivatives. C 2001 Elsevier Science Ltd. All rights reserved.