ethyl 2-methyl-1-indolizinecarboxylate | 31108-60-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: ethyl 2-methyl-1-indolizinecarboxylate
• 英文别名: ethyl 2-methylindolizine-1-carboxylate；2-Methyl-indolizincarbonsaeure-(1)-ethylester；2-Methyl-1-ethoxycarbonyl-indolizin；1-Carbethoxy-2-methyl-indolizin；2-methyl-indolizine-1-carboxylic acid ethyl ester；2-Methyl-1-indolizinecarboxylic acid ethyl ester
• CAS: 31108-60-8
• 化学式: C₁₂H₁₃NO₂
• 分子量: 203.241
• InChiKey: AEVIPPKEGKHLRI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl 2-methyl-1-indolizinecarboxylate 、 原甲酸三乙酯 在 硫酸 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以79%的产率得到tris<1-(ethoxycarbonyl)-2-methyl-3-indolizinyl>methane
  参考文献：
  名称：

  Ceder, Olof; Sharif, Mohammed Rashid, Chemische Berichte, 1987, vol. 120, p. 239 - 242

  摘要：

  DOI：
• 作为产物：
  描述：

  生成 ethyl 2-methyl-1-indolizinecarboxylate
  参考文献：
  名称：

  亚甲基环丙烷成环/开环级联的吲哚嗪

  摘要：

  已经开发了合成多取代的吲哚嗪的独特策略。当用Cs 2 CO 3处理2-吡啶基-2-（2'-溴烯丙基）-1-羧酸盐时，起始原料经过亚甲基环丙烷成环/开环级联反应，得到相应的吲哚嗪类化合物，收率中等至良好。一个单一的区域异构体。

  DOI：

  10.1021/acs.joc.7b01073

文献信息

• Copper-catalyzed formal [1 + 2 + 2]-annulation of alkyne-tethered diazoacetates and pyridines: access to polycyclic indolizines
  作者：Shanliang Dong、Jingjing Huang、Hongkai Sha、Lihua Qiu、Wenhao Hu、Xinfang Xu

  DOI：10.1039/d0ob00222d

  日期：——

  A copper-catalyzed formal [1 + 2 + 2]-annulation of alkyne-tethered diazo compounds with pyridines, which affords polycyclic fused indolizines in synthetically useful to good yields under mild reaction conditions, has been reported. This method features the use of an inexpensive copper catalyst and readily available starting materials, broad substrate generality, and operational simplicity. Notably

  据报导，铜连接的炔烃系重氮化合物与吡啶的正式[1 + 2 + 2]环化反应，可在温和的反应条件下提供多环稠合的吲哚并嗪，可合成用于高产。该方法的特点是使用廉价的铜催化剂和易于获得的起始原料，广泛的底物通用性和操作简便性。值得注意的是，多种天然产物衍生物在当前条件下是相容的，这表明该方法用于选择性修饰和修饰类似生物分子或药物的巨大潜力。
• Desulfitative palladium-catalyzed direct C-3 arylation of indolizines with arylsulfonyl chlorides
  作者：Wei Zhang、Fang Liu、Baoli Zhao

  DOI：10.1002/aoc.3326

  日期：2015.8

  Pd‐catalyzed desulfitative approach to C‐3 arylation of indolizine derivatives has been developed, and the protocol uses readily available arylsulfonyl chlorides as the arylation reagent under nitrogen. This transformation was performed in a mixed solvent of 1‐methyl‐2‐pyrrolidone and dimethoxyethane using simple triphenylphosphine as a ligand, which provides a new method for the C‐3 arylation of indolizines

  已经开发了一种高效的Pd催化的吲哚嗪衍生物C-3芳基化脱硫方法，并且该方案使用易于获得的芳基磺酰氯作为氮气氛下的芳基化试剂。这种转化是在1-甲基-2-吡咯烷酮和二甲氧基乙烷的混合溶剂中使用简单的三苯基膦作为配体进行的，这为吲哚嗪的C-3芳基化提供了一种新方法。版权所有©2015 John Wiley＆Sons，Ltd.
• Pyridine Activation via Copper(I)-Catalyzed Annulation toward Indolizines
  作者：José Barluenga、Giacomo Lonzi、Lorena Riesgo、Luis A. López、Miguel Tomás

  DOI：10.1021/ja106751t

  日期：2010.9.29

  cyclization of pyridines toward alkenyldiazoacetates leading to functionalized indolizine derivatives is reported. A broad range of pyridine derivatives (including quinoline and isoquinoline) is compatible with this cyclization reaction. The process represents the first successful example of metal-catalyzed cyclization of a π-deficient heterocyclic system with alkenyldiazo compounds.

  报道了铜 (I) 催化的吡啶区域选择性 [3 + 2] 环化反应生成烯基重氮乙酸酯，从而生成功能化的吲哚嗪衍生物。广泛的吡啶衍生物（包括喹啉和异喹啉）与该环化反应相容。该过程代表了金属催化环化 π 缺陷杂环系统与烯基重氮化合物的第一个成功例子。
• C3 functionalization of indolizines via In(<scp>iii</scp>)-catalyzed three-component reaction
  作者：Youngeun Jung、Ikyon Kim

  DOI：10.1039/c5ob01657f

  日期：——

  Post-functionalization at the C3 position of indolizines via In(III)-catalyzed three-component coupling reaction with amines and aldehydes allowed rapid access to a new class of indolizines with diverse functional groups at the C3 position in good to excellent yields.

  通过In（III）催化的三组分与胺和醛的偶合反应，在吲哚嗪的C3位置进行后官能化，可以快速获得具有优异收率的新型C位置的具有不同官能团的吲哚嗪类。
• Novel 1,2,3-substituted indolizine derivatives, inhibitors of fgfs, method for making same and pharmaceutical compositions containing same
  申请人：Badorc Alain

  公开号：US20050203126A1

  公开（公告）日：2005-09-15

  Compounds of formula I or salts thereof: in which R 1 represents —OH, (C 1 -C 5 )alkoxy, carboxyl, (C 2 -C 6 )alkoxycarbonyl, —NR 5 R 6 , —NH—SO 2 -Alk, —NH—SO 2 -Ph, —NH—CO-Ph, —N(Alk)-CO-Ph, —NH—CO—NH-Ph, —NH—CO-Alk, —NH—CO 2 -Alk, —O—(CH 2 ) n -cAlk, —O-Alk-COOR 7 , —O-Alk-O—R 8 , —O-Alk-OH, —O-Alk-C(NH 2 ):NOH, —O-Alk-NR 5 R 6 , —O-Alk-CN, —O—(CH 2 ) n -Ph, —O-Alk-CO—NR 5 R 6 , —CO—NH—(CH 2 ) m —COOR 7 , —CO—NH-Alk R 2 represents H, (C 1 -C 5 )alkyl, (C 1 -C 5 )alkyl halide, (C 3 -C 6 )cycloalkyl or phenyl which is optionally substituted, A represents —CO—, —SO— or —SO 2 —, R 3 and R 4 which are identical or different, each represent H, (C 1 -C 5 )alkoxy, amino, carboxyl, (C 2 -C 6 )alkoxycarbonyl, —OH, nitro, hydroxyamino, -Alk-COOR 7 , —NR 5 R 6 , —NH-Alk-COOR 7 , —NH—COO-Alk, —N(R 11 )—SO 2 -Alk-NR 9 R 10 , —N(R 11 )—SO 2 -Alk, —N(R 11 )-Alk-NR 5 R 6 , —N(R 11 )—CO-Alk-NR 9 R 10 , —N(R 11 )—CO-Alk, —N(R 11 )—CO—CF 3 , —NH-Alk-HetN, —O-Alk-NR 9 R 10 , —O-Alk-CO—NR 5 R 6 , —O-Alk-HetN, or R 3 and R 4 form together a 5- to 6-membered unsaturated heterocycle, are inhibitors of basic fibroblast growth factors.

  化合物I的公式或其盐：其中R1表示-OH，（C1-C5）烷氧基，羧基，（C2-C6）烷氧羰基，-NR5R6，-NH-SO2-Alk，-NH-SO2-Ph，-NH-CO-Ph，-N（Alk）-CO-Ph，-NH-CO-NH-Ph，-NH-CO-Alk，-NH-CO2-Alk，-O-（CH2）n- cAlk，-O-Alk-COOR7，-O-Alk-O-R8，-O-Alk-OH，-O-Alk-C（NH2）：NOH，-O-Alk-NR5R6，-O-Alk-CN，-O-（CH2）n-Ph，-O-Alk-CO-NR5R6，-CO-NH-（CH2）m-COOR7，-CO-NH-Alk。R2表示氢，（C1-C5）烷基，（C1-C5）烷基卤代，（C3-C6）环烷基或苯基，其可以被取代。A表示-CO-，-SO-或-SO2-，R3和R4相同或不同，每个表示氢，（C1-C5）烷氧基，氨基，羧基，（C2-C6）烷氧羰基，-OH，硝基，羟基氨基，-Alk-COOR7，-NR5R6，-NH-Alk-COOR7，-NH-COO-Alk，-N（R11）-SO2-Alk-NR9R10，-N（R11）-SO2-Alk，-N（R11）-Alk-NR5R6，-N（R11）-CO-Alk-NR9R10，-N（R11）-CO-Alk，-N（R11）-CO-CF3，-NH-Alk-HetN，-O-Alk-NR9R10，-O-Alk-CO-NR5R6，-O-Alk-HetN，或R3和R4共同形成5-至6-成员不饱和杂环，是基本成纤维细胞生长因子的抑制剂。