ethyl 6-(phenylamino)hex-2-ynoate | 1432629-23-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: ethyl 6-(phenylamino)hex-2-ynoate
• 英文别名: Ethyl 6-anilinohex-2-ynoate；ethyl 6-anilinohex-2-ynoate
• CAS: 1432629-23-6
• 化学式: C₁₄H₁₇NO₂
• 分子量: 231.294
• InChiKey: UVXOTTQBKYJMNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 6-(phenylamino)hex-2-ynoate 在 氧气 、 palladium diacetate 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 以63%的产率得到ethyl 2,3-dihydro-1H-pyrrolo[1,2-a]indole-9-carboxylate
  参考文献：
  名称：

  Pd(II)-catalyzed intramolecular aminopalladation/direct C–H arylation under aerobic conditions: synthesis of pyrrolo[1,2-a]indoles

  摘要：

  Heating a DMA/pivalic acid (v/v=4/1) solution of diversely substituted 6-(phenylamino)hex-2-ynoates in the presence of a catalytic amount of Pd(OAc)(2) under oxygen atmosphere afforded pyrrolo[1,2-a]indoles in moderate to good yields. A domino sequence involving intramolecular aminopalladation followed by C-H activation and reductive elimination was proposed to account for the observed bis-cyclization. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.01.003
• 作为产物：
  描述：

  ethyl 6-((tert-butoxycarbonyl)(phenyl)amino)hex-2-ynoate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以50%的产率得到ethyl 6-(phenylamino)hex-2-ynoate
  参考文献：
  名称：

  Pd(II)-catalyzed intramolecular aminopalladation/direct C–H arylation under aerobic conditions: synthesis of pyrrolo[1,2-a]indoles

  摘要：

  Heating a DMA/pivalic acid (v/v=4/1) solution of diversely substituted 6-(phenylamino)hex-2-ynoates in the presence of a catalytic amount of Pd(OAc)(2) under oxygen atmosphere afforded pyrrolo[1,2-a]indoles in moderate to good yields. A domino sequence involving intramolecular aminopalladation followed by C-H activation and reductive elimination was proposed to account for the observed bis-cyclization. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.01.003

文献信息

• Pd(II)-catalyzed intramolecular aminopalladation/direct C–H arylation under aerobic conditions: synthesis of pyrrolo[1,2-a]indoles
  作者：Tiffany Piou、Luc Neuville、Jieping Zhu

  DOI：10.1016/j.tet.2013.01.003

  日期：2013.6

  Heating a DMA/pivalic acid (v/v=4/1) solution of diversely substituted 6-(phenylamino)hex-2-ynoates in the presence of a catalytic amount of Pd(OAc)(2) under oxygen atmosphere afforded pyrrolo[1,2-a]indoles in moderate to good yields. A domino sequence involving intramolecular aminopalladation followed by C-H activation and reductive elimination was proposed to account for the observed bis-cyclization. (C) 2013 Elsevier Ltd. All rights reserved.