2-benzoyl-3,4-diethylpyrrole | 137018-23-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-benzoyl-3,4-diethylpyrrole
• 英文别名: (3,4-diethyl-1H-pyrrol-2-yl)-phenylmethanone
• CAS: 137018-23-6
• 化学式: C₁₅H₁₇NO
• 分子量: 227.306
• InChiKey: NNPXDUZYVJXFJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.37
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  32.86
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-benzoyl-3,4-diethylpyrrole 在 盐酸 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 乙醇 、 丙酸 为溶剂， 生成 5,10-diphenyl-2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyne
  参考文献：
  名称：

  Selective syntheses of unsymmetrical meso-arylporphyrins

  摘要：

  A selective synthetic route to unsymmetrical meso-arylporphyrins is described. New hybrid type of unsymmetrical porphyrin with C2-nu symmetry was prepared according to the new method.

  DOI：

  10.1016/0040-4039(91)80031-z
• 作为产物：
  描述：

  3,4-二乙基吡咯 、 苯甲酰氯 在 乙基溴化镁 作用下， 生成 2-benzoyl-3,4-diethylpyrrole
  参考文献：
  名称：

  Selective syntheses of unsymmetrical meso-arylporphyrins

  摘要：

  A selective synthetic route to unsymmetrical meso-arylporphyrins is described. New hybrid type of unsymmetrical porphyrin with C2-nu symmetry was prepared according to the new method.

  DOI：

  10.1016/0040-4039(91)80031-z

文献信息

• One-Pot Synthesis of Butadiyne-Bridged Bipyrrole Derivatives and Bisporphyrin
  作者：M. V. Nanda Kishore、Pradeepta K. Panda

  DOI：10.1002/ejoc.201700891

  日期：2017.9.25

  A facile one-pot synthesis of butadiyne bridged bipyrroles could be achieved from 2-iodopyrroles and trimethylsilylacetylene via a modified Sonogashira coupling and in-situ aerial oxidative coupling of the acetylenic pyrroles in 31-72% yields, depending upon the substituents on pyrrole. The acetylene bridged diacids obtained from hydrolysis of the corresponding ester derivatives were highly stable

  可以通过修饰的Sonogashira偶联和炔吡咯的原位空中氧化偶联，以31-72％的收率（取决于吡咯上的取代基）由2-碘吡咯和三甲基甲硅烷基乙炔轻松完成一丁二烯桥接的双吡咯的一锅合成。通过水解相应的酯衍生物获得的乙炔桥二酸是高度稳定的，这与大多数报道的低聚吡咯二酸不同。该协议可以很容易地扩展到丁二炔桥联的双卟啉的合成。
• Design and Synthesis of a Trifunctional Chiral Porphyrin with C2 Symmetry as a Chiral Recognition Host for Amino Acid Esters
  作者：Tadashi Mizutani、Tadashi Ema、Takashi Tomita、Yasuhisa Kuroda、Hisanobu Ogoshi

  DOI：10.1021/ja00089a013

  日期：1994.5

  An intrinsic chiral recognition host, (R,R)- or (S,S)-[trans-5,15-bis(2-hydroxyphenyl)-10-2,6-bis((methoxycarbonyl)methyl)phenyl}-2,3,17,18-tetraethylporphyrinato]zinc(II) (1), was synthesized by the coupling between (3,3',4,4'-tetraethyl-5,5'-bis(alpha-hydroxy-2-methoxybenzyl)-2,2'-dipyrryl)methane (8) and dimethyl 2-(bis(2-pyrryl)-methyl)-1, 3-benzenediacetate (16). This pyrrylmethanol method made it possible to perform the regiospecific coupling between differently functionalized dipyrromethane units. Host 1 was designed to have three recognition elements: metal coordination, hydrogen bond donor, and hydrogen bond acceptor (and/or steric repulsion) groups. These groups are arranged in a convergent fashion, forming a chiral recognition pocket. Host 1 was resolved into two enantiomers, (+)-1 and (-)-1. The binding constants in CHCl3 were determined by UV-vis titration. Host (+)-1 was found to show an enantioselectivity of 2.0-2.8 in respect to L- and D-enantiomers of Ile-OMe, Leu-OMe, Leu-OBzl, Val-OMe, Pro-OMe, and Phe-OMe. Host (+)-1 showed an enantioselectivity of 0.47 in respect to L- and D-enantiomers of serine benzyl ester, indicating that the enantioselectivity was reversed. Reference porphyrins 2-4, which lack some of recognition groups, were also synthesized by the pyrrylmethanol method to clarify the roles of the recognition groups of (+)-1 in thermodynamics of the binding processes. Total free energy change upon binding of L- and D-Ile-OMe to host (+)-1 (Delta G degrees(total) for L, -5.05, and D, -4.46 kcal/mol) was separated into three terms: metal coordination energy (Delta G degrees(Zn)), -4.15 kcal/mol; hydrogen bond energy (Delta Delta G degrees(OH)), -1.30 kcal/mol; and steric repulsion energy (Delta Delta G degrees(COOMe)(L) or Delta Delta G degrees(COOMe)(D)), +0.40 kcal/mol for L- and +0.99 kcal/mol for D-Ile-OMe. The third recognition group (CH(2)CO(2)Me) of (+)-1 was found to destabilize the complexes due to steric repulsions. In contrast, the CH(2)CO(2)Me group was found to stabilize the complex between D-Ser-OBzl and (+)-1, suggesting that hydrogen bonding between the OH group of serine and the C=O group of (+)-1 takes place. On the basis of these thermodynamic studies, chiral recognition was found to be achieved by cooperative functions of these three recognition groups.