3,3'-di-iso-propyloxycarbonyl-2,2'-bipyridine | 39775-34-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3,3'-di-iso-propyloxycarbonyl-2,2'-bipyridine
• 英文别名: 2,2'-(5,5'-Di-isopropoxycarbonyl)-dipyridyl；[2,2']bipyridinyl-3,3'-dicarboxylic acid diisopropyl ester；Isopropyl 2-(3-isopropoxycarbonyl-2-pyridyl)pyridine-3-carboxylate；propan-2-yl 2-(3-propan-2-yloxycarbonylpyridin-2-yl)pyridine-3-carboxylate
• CAS: 39775-34-3
• 化学式: C₁₈H₂₀N₂O₄
• 分子量: 328.368
• InChiKey: ALRRJLGHFXRWCO-UHFFFAOYSA-N

物化性质

• 沸点：
  457.8±45.0 °C(Predicted)
• 密度：
  1.157±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  78.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  sodium tetrachloropalladate(II) 、 二氯甲烷 、 3,3'-di-iso-propyloxycarbonyl-2,2'-bipyridine 以 甲醇 、 甲苯 为溶剂， 以65%的产率得到
  参考文献：
  名称：

  Pd(II) complexes with 3,3′-substituted bipyridine ligands: Synthesis, crystal structure, DFT calculations and catalytic studies in compressed carbon dioxide

  摘要：

  Cationic bis(chelated) complexes [Pd(N-N)(2)][BArF](2) with N-N = 3,3'-diester-2,2'-bipyridine ligands were prepared and tested as catalyst for the CO/tert-butylstyrene copolymerization using compressed carbon dioxide as a solvent. The NMR analysis of these complexes suggests the formation of several species in solution. A detailed DFT calculation analysis indicated that these species correspond to different relative orientations of the carbonyl group. These complexes showed poor catalytic activity towards the formation of polyketones, producing only poly(tert-butylstyrene) when trifluoroethanol was used as a solvent. The use of compressed carbon dioxide favored the formation of the polyketones when the complexes with methyl and isopropyl ester derivatives were employed as catalysts. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2013.09.053
• 作为产物：
  描述：

  2,2'-联吡啶-3,3'-二羧酸 、 异丙醇 在 氯化亚砜 、 氯 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以73%的产率得到3,3'-di-iso-propyloxycarbonyl-2,2'-bipyridine
  参考文献：
  名称：

  Novel Cytotoxic Oxopyridoindolizines: iso-Propyl-7,8,9-trichloro-6,7,8,9-tetrahydro-5-oxopyrido[2,3-a]-indolizine-10-carboxylates (OPIC)

  摘要：

  通过 2,2'-联吡啶-3,3'-二羧酸（BPA）与亚硫酰氯/氯的混合物反应，然后加入适当的醇，制备了一系列八种新的烷基-7,8,9-三氯-6,7,8,9-四氢-5-氧代吡啶并[2,3-a]-吲哚嗪-10-羧酸盐（OPIC），它们是喜树碱（CPT）的类似物。这样就得到了 OPIC 化合物 3a-d、4a-d 和 3,3'-二烷氧基羰基-2,2'-联吡啶（BPE，2a-d）的混合物。与其他类似物相比，异丙基 OPIC 3c 及其相应的非对映异构体 4c 对三种癌症细胞株具有明显的活性。因此，与其他烷基取代基相比，羧酸酯上异丙基取代基的存在似乎对这一类新化合物的细胞毒性效力起着关键作用。

  DOI：

  10.3390/70800628

文献信息

• Pd(II) complexes with 3,3′-substituted bipyridine ligands: Synthesis, crystal structure, DFT calculations and catalytic studies in compressed carbon dioxide
  作者：Ariadna Campos-Carrasco、Marlene Bruce、Mar Reguero、Anna M. Masdeu-Bultó

  DOI：10.1016/j.ica.2013.09.053

  日期：2014.1

  Cationic bis(chelated) complexes [Pd(N-N)(2)][BArF](2) with N-N = 3,3'-diester-2,2'-bipyridine ligands were prepared and tested as catalyst for the CO/tert-butylstyrene copolymerization using compressed carbon dioxide as a solvent. The NMR analysis of these complexes suggests the formation of several species in solution. A detailed DFT calculation analysis indicated that these species correspond to different relative orientations of the carbonyl group. These complexes showed poor catalytic activity towards the formation of polyketones, producing only poly(tert-butylstyrene) when trifluoroethanol was used as a solvent. The use of compressed carbon dioxide favored the formation of the polyketones when the complexes with methyl and isopropyl ester derivatives were employed as catalysts. (C) 2013 Elsevier B.V. All rights reserved.
• Novel Cytotoxic Oxopyridoindolizines: iso-Propyl-7,8,9-trichloro-6,7,8,9-tetrahydro-5-oxopyrido[2,3-a]-indolizine-10-carboxylates (OPIC)
  作者：Franco Zunino、Ann Kotchevar、Michael Waring、Maria Daoudi、Najib Larbi、Mostafa Mimouni、Najat Sam、Assou Zahidi、Taibi Ben-Hadda

  DOI：10.3390/70800628

  日期：——

  A series of eight new alkyl-7,8,9-trichloro-6,7,8,9-tetrahydro-5-oxopyrido[2,3-a]-indolizine-10-carboxylates (OPIC), analogues of camptothecin (CPT), were prepared in a one-pot reaction of 2,2'-bipyridine-3,3'-dicarboxylic acid (BPA) with a mixture of thionyl chloride/chlorine, followed by addition of the appropriate alcohol. This led to a mixture of OPIC compounds 3a-d, 4a-d and 3,3'-dialkoxycarbonyl-2,2'-bipyridines (BPE, 2a-d). The isopropyl OPIC 3c and its corresponding diastereoisomer 4c showed marked activity against three cancer cell lines compared to other analogs. These same diastereoisomers also displayed high cytotoxic activity against five leukemia cell lines, thus the presence of an isopropyl substituent on the carboxylic ester, as opposed to other alkyl substituents, appears to play a key role in the cytotoxic potency of this new class of compounds.

  通过 2,2'-联吡啶-3,3'-二羧酸（BPA）与亚硫酰氯/氯的混合物反应，然后加入适当的醇，制备了一系列八种新的烷基-7,8,9-三氯-6,7,8,9-四氢-5-氧代吡啶并[2,3-a]-吲哚嗪-10-羧酸盐（OPIC），它们是喜树碱（CPT）的类似物。这样就得到了 OPIC 化合物 3a-d、4a-d 和 3,3'-二烷氧基羰基-2,2'-联吡啶（BPE，2a-d）的混合物。与其他类似物相比，异丙基 OPIC 3c 及其相应的非对映异构体 4c 对三种癌症细胞株具有明显的活性。因此，与其他烷基取代基相比，羧酸酯上异丙基取代基的存在似乎对这一类新化合物的细胞毒性效力起着关键作用。