ethyl 1-butyl-2,5-dimethyl-1H-pyrrole-3-carboxylate | 107411-79-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: ethyl 1-butyl-2,5-dimethyl-1H-pyrrole-3-carboxylate
• 英文别名: 1-butyl-2,5-dimethyl-pyrrole-3-carboxylic acid ethyl ester；1-Butyl-2,5-dimethyl-pyrrol-3-carbonsaeure-aethylester；Ethyl 1-butyl-2,5-dimethylpyrrole-3-carboxylate
• CAS: 107411-79-0
• 化学式: C₁₃H₂₁NO₂
• 分子量: 223.315
• InChiKey: NXPQSWBUJKCEJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl 1-butyl-2,5-dimethyl-1H-pyrrole-3-carboxylate 、 二乙氨基乙醇 在 sodium 2-(diethylamino)ethanolate 作用下， 生成 1-butyl-2,5-dimethyl-pyrrole-3-carboxylic acid-(2-diethylamino-ethyl ester)
  参考文献：
  名称：

  Monoalkamine esters of pyrrole-3-carboxylic acids

  摘要：

  公开号：

  US02500713A1
• 作为产物：
  描述：

  ethyl (2Z)-2-[1-(butylamino)ethylidene]pent-4-ynoate 在 zinc(II) nitrate 作用下， 以 乙腈 为溶剂， 反应 0.02h， 生成 ethyl 1-butyl-2,5-dimethyl-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  An assessment of late transition metals as hydroamination catalysts in the cyclization of C-propargyl vinylogous amides into pyrroles

  摘要：

  It has been shown that common and inexpensive salts of the late transition metals serve as effective hydroamination catalysts in the conversion of C-propargyl vinylogous amides into pyrroles. The oxide, acetate, nitrate and chloride derivatives of Cu(II), Ag(I), Zn(II), Cd(II) and Hg(II) were utilized as hydroamination catalysts in the oxidation states shown. Although the Zn(II) catalysts with the exception of ZnO afforded the highest yields of product under mild conditions, all of the group 12 metal catalysts provided excellent yields of product under more forcing conditions. The nature of the counterion plays an important role in the efficiency of hydroamination reactions, as well as the Lewis acidity of the metal centre. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.11.116

文献信息

• Indium-Catalyzed Synthesis of Furans and Pyrroles via Cyclization of α-Propargyl-β-keto Esters
  作者：Hayato Tsuji、Eiichi Nakamura、Ken-ichi Yamagata、Yasuyuki Ueda

  DOI：10.1055/s-0030-1259930

  日期：2011.4

  organic reactions involving carbonylgroups, 1 such as the Barbier reaction, 2 aldol reaction, 3 andHosomi–Sakurai reaction. 4 Indium can also activate C–Ctriple bonds to form new C–C bonds, because of its soft-ness, as reported by us 5 and others. 6 Formation of carbon–heteroatom bonds via activation of triple bonds has alsobeen reported. For instance, Tan et al. 7a described that 10mol% of InCl 3 promotes

  摘要：In(OTf) 3 或In(NTf 2 ) 3 可有效催化α-炔丙基-b-酮酯及其亚胺类似物的环异构化反应，分别生成三取代的呋喃和吡咯。该反应在少量催化剂存在下具有良好的官能团相容性。关键词：铟催化剂，酮酯，环化，呋喃，吡咯 铟试剂和催化剂的效用已被涉及羰基的有机反应广泛证明，1如Barbier反应，2羟醛反应，3和Hosomi-Sakurai反应。4 铟还可以激活 C-Ctriple 键以形成新的 C-C 键，因为它具有柔软性，正如我们 5 和其他人报道的那样。6 还报道了通过激活三键形成碳-杂原子键。例如，谭等人。图 7a 描述了 10mol% 的 InCl 3 通过串联反应促进呋喃衍生物的一锅合成，该反应涉及炔丙醇和 1,3-二羰基化合物（主要是 1,3-二酮）在回流氯气中的分子间缩合反应。苯。在此我们报告 In(OTf)
• Pyrrole dyes and methods of making them
  申请人：EASTMAN KODAK CO

  公开号：US02725378A1

  公开（公告）日：1955-11-29
• Timoschewskaja, Zhurnal Obshchei Khimii, 1939, vol. 9, p. 406,407
  作者：Timoschewskaja

  DOI：——

  日期：——
• Monoalkamine esters of pyrrole-3-carboxylic acids
  申请人：AMERICAN CYANAMID CO

  公开号：US02500713A1

  公开（公告）日：1950-03-14
• An assessment of late transition metals as hydroamination catalysts in the cyclization of C-propargyl vinylogous amides into pyrroles
  作者：Allan M. Prior、Ross S. Robinson

  DOI：10.1016/j.tetlet.2007.11.116

  日期：2008.1

  It has been shown that common and inexpensive salts of the late transition metals serve as effective hydroamination catalysts in the conversion of C-propargyl vinylogous amides into pyrroles. The oxide, acetate, nitrate and chloride derivatives of Cu(II), Ag(I), Zn(II), Cd(II) and Hg(II) were utilized as hydroamination catalysts in the oxidation states shown. Although the Zn(II) catalysts with the exception of ZnO afforded the highest yields of product under mild conditions, all of the group 12 metal catalysts provided excellent yields of product under more forcing conditions. The nature of the counterion plays an important role in the efficiency of hydroamination reactions, as well as the Lewis acidity of the metal centre. (C) 2007 Elsevier Ltd. All rights reserved.