methyl 6-(phenylamino)hex-2-ynoate | 1432476-77-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: methyl 6-(phenylamino)hex-2-ynoate
• CAS: 1432476-77-1
• 化学式: C₁₃H₁₅NO₂
• 分子量: 217.268
• InChiKey: LYOINVGXDKQROZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.06
• 重原子数：
  16.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  38.33
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl 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51%的产率得到Methyl 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：

  N-phenylpent-4-ynamide 在 lithium aluminium tetrahydride 、 正丁基锂 、 三氟乙酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 叔丁醇 为溶剂， 反应 48.5h， 生成 methyl 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 aerobic oxidative intramolecular hydroamination and C–H functionalization of N-alkynyl anilines for the synthesis of indole derivatives
  作者：Long Ren、Zhuangzhi Shi、Ning Jiao

  DOI：10.1016/j.tet.2013.01.031

  日期：2013.6

  A Pd(II)-catalyzed aerobic oxidative approach to 2,3-dihydro-1H-pyrrolo[1,2-a]indoles from simple N-alkynyl anilines through tandem intramolecular hydroamination and aryl C-H activation process has been developed. Molecular oxygen was used as the sole oxidant to recycle the Pd-catalysis. This protocol is attractive due to the available starting materials and the valuable products. (C) 2013 Elsevier Ltd. All rights reserved.