N,N-dimethyl-2-((2-(phenylethynyl)phenyl)ethynyl)aniline | 1258410-52-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N,N-dimethyl-2-((2-(phenylethynyl)phenyl)ethynyl)aniline
• 英文别名: N,N-dimethyl-2-((2-(phenylethynyl)phenyl)ethynyl)benzenamine；N,N-dimethyl-2-[2-[2-(2-phenylethynyl)phenyl]ethynyl]aniline
• CAS: 1258410-52-4
• 化学式: C₂₄H₁₉N
• 分子量: 321.422
• InChiKey: FEYLJCREBLGTHY-UHFFFAOYSA-N

物化性质

• 沸点：
  500.5±35.0 °C(predicted)
• 密度：
  1.14±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N,N-dimethyl-2-((2-(phenylethynyl)phenyl)ethynyl)aniline 在 copper(ll) bromide 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以88%的产率得到3-chloro-1-methyl-2-(2-(phenylethynyl)phenyl)-1H-indole
  参考文献：
  名称：

  Synthetic Development and Mechanistic Study on Pd(II)-Catalyzed Cyclization of Enediynes to Benzo[a]carbazoles

  摘要：

  Treatment of N,N-dimethyl 2[2-(2-ethynylphenyl)ethynyl]anilines (1) with 10 mol he of palladium chloride and 2 equiv of cupric chloride in refluxing THF gave benzo[a]carbazoles (6) in good yields. A mechanistic study showed that this reaction must proceed through formation of haloindole (7) followed by a palladium(II)-catalyzed atom transfer cyclization reaction to give the benzo[a]carbazoles.

  DOI：

  10.1021/ol1024458
• 作为产物：
  描述：

  邻碘-N,N-二甲基苯胺 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 34.0h， 生成 N,N-dimethyl-2-((2-(phenylethynyl)phenyl)ethynyl)aniline
  参考文献：
  名称：

  TBAI / TBHP介导的磺酰化茚并[1,2- c ]喹啉级联环化反应

  摘要：

  的治疗邻-氨基取代的衍生物aryldiyne在四丁基碘化铵（TBAI）的存在和磺酰基酰肼叔丁基过氧化氢（TBHP）导致级联环化反应，得到磺酰基茚并[1,2- Ç〕喹啉在中度至良品率高。该方法的特点包括无金属反应，易于处理试剂和宽泛的官能团耐受性。

  DOI：

  10.1021/acs.orglett.7b03246

文献信息

• Iodine-Mediated Cascade Cyclization of Enediynes to Iodinated Benzo[<i>a</i>]carbazoles
  作者：Chin-Chau Chen、Shyh-Chyun Yang、Ming-Jung Wu

  DOI：10.1021/jo201795t

  日期：2011.12.16

  Treatment of N,N-dimethyl 2-[2-(2-ethynylphenyl)ethynyl]anilines (1) with 1.2 equiv of iodine in CH2Cl2 gave benzo[a]carbazoles (2) in good yields. Mechanistic studies showed this reaction must go through the haloindole (3) followed by iodonium ion catalyzed atom-transfer cyclization reaction to give the benzo[a]carbazoles.
• TBAI/TBHP-Mediated Cascade Cyclization toward Sulfonylated Indeno[1,2-<i>c</i>]quinolines
  作者：Jatuporn Meesin、Manat Pohmakotr、Vichai Reutrakul、Darunee Soorukram、Pawaret Leowanawat、Saowanit Saithong、Chutima Kuhakarn

  DOI：10.1021/acs.orglett.7b03246

  日期：2017.12.15

  aryldiyne derivatives with sulfonyl hydrazides in the presence of tetrabutylammonium iodide (TBAI) and tert-butyl hydroperoxide (TBHP) led to a cascade cyclization reaction to yield sulfonylated indeno[1,2-c]quinolines in moderate to good yields. The features of the methodology include metal-free reaction, the ease of reagent handling, and a broad functional group tolerance.

  的治疗邻-氨基取代的衍生物aryldiyne在四丁基碘化铵（TBAI）的存在和磺酰基酰肼叔丁基过氧化氢（TBHP）导致级联环化反应，得到磺酰基茚并[1,2- Ç〕喹啉在中度至良品率高。该方法的特点包括无金属反应，易于处理试剂和宽泛的官能团耐受性。
• Synthetic Development and Mechanistic Study on Pd(II)-Catalyzed Cyclization of Enediynes to Benzo[<i>a</i>]carbazoles
  作者：Chin-Chau Chen、Lin-Yu Chin、Shyh-Chyun Yang、Ming-Jung Wu

  DOI：10.1021/ol1024458

  日期：2010.12.17

  Treatment of N,N-dimethyl 2[2-(2-ethynylphenyl)ethynyl]anilines (1) with 10 mol he of palladium chloride and 2 equiv of cupric chloride in refluxing THF gave benzo[a]carbazoles (6) in good yields. A mechanistic study showed that this reaction must proceed through formation of haloindole (7) followed by a palladium(II)-catalyzed atom transfer cyclization reaction to give the benzo[a]carbazoles.