ethyl 3,4-diethyl-5-formyl-1H-pyrrole-2-carboxylate | 100370-73-8

• 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 3,4-diethyl-5-formyl-1H-pyrrole-2-carboxylate
• 英文别名: ethyl 3,4-diethyl-5-formyl-pyrrole-2-carboxylate；ethyl 3,4-diethyl-5-formylpyrrole-2-carboxylate；ethyl 5-formyl-3,4-diethylpyrrole-2-carboxylate；3,4-diethyl-5-formyl-2-carboethoxy-1H-pyrrole；3,4-diethyl-5-formyl-pyrrole-2-carboxylic acid ethyl ester；3,4-Diaethyl-5-formyl-pyrrol-2-carbonsaeure-aethylester
• CAS: 100370-73-8
• 化学式: C₁₂H₁₇NO₃
• 分子量: 223.272
• InChiKey: RKSVHXHNIAQJKV-UHFFFAOYSA-N

物化性质

• 熔点：
  53 °C
• 沸点：
  370.2±42.0 °C(Predicted)
• 密度：
  1.119±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  59.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 3,4-diethyl-5-formyl-1H-pyrrole-2-carboxylate 在 氢氧化钾 、 sodium tetrahydroborate 、 potassium acetate 、 sodium acetate 、 四氯化锡 作用下， 以 甲醇 、 二氯甲烷 、 水 、 异丙醇 为溶剂， 反应 10.67h， 生成 9-(2-methylbenzyl)-3,4-dimethyl-7,8-diethyl-dipyrrinone
  参考文献：
  名称：

  Stereochemistry and Conformational Analysis of Hemirubin

  摘要：

  Intramolecularly hydrogen-bonded analogs of the natural bile pigment, bilirubin, are very scarce. Nuclear Overhauser effect NMR studies of the newest analog, a hemirubin (1), confirms intramolecular hydrogen bonding and a ridge-tile-shaped conformation. H-1 NMR studies of 1 at sufficiently low temperatures detect conformational enantiomerization, for which an activation barrier of Delta G(double dagger)similar to 16 kcal/mol at 25 degrees C in CDCl3 has been estimated. Evidence for the presence of dimeric association at low temperatures or high concentrations of 1 is found by the appearance of new sets of resonances, data from which may be used to calculate: Delta G degrees(298) (K) + 3.4 kca/mol, Delta H degrees - 5.6 kcal/mol and Delta S degrees -30.3 cal/deg/mol. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00087-9
• 作为产物：
  描述：

  3,4-二乙基-5-甲基-2-吡咯羧酸乙酯 在 ammonium cerium(IV) nitrate 作用下， 以 四氢呋喃 、 水 、 溶剂黄146 为溶剂， 反应 2.0h， 以75%的产率得到ethyl 3,4-diethyl-5-formyl-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  An Intramolecularly Hydrogen Bonded Dihydrotripyrrinone

  摘要：

  A yellow tripyrrole analog (1) of bilirubin has been synthesized, and its lone propionic acid group is found to engage in conformation determining, intramolecular hydrogen bonding in solution and in the crystal. Molecular modelling and X-ray crystallography reveal an abbreviated ridge-tile or L-shape conformation in which an essentially planar dipyninone is hydrogen bonded to the single opposing propionic acid group. In the (arbitrary) (P)-helicity ridge-tile, the torsion angles about C(10) are computed to be 55 degrees and 61 degrees by molecular dynamics and found to be 66 degrees and 53 degrees in the crystal. Such torsion angles lead to an interplanar dihedral angle (similar to 93 degrees) between the dipyninone and its adjoining pyrrole that is very close to the dihedral angle (similar to 98 degrees) found in intramolecularly hydrogen bonded bilirubin.

  DOI：

  10.1007/pl00010223

文献信息

• Substituents modification of meso-aryl BODIPYs for tuning photophysical properties
  作者：Sangwon Ko、Cheul Yong Kim、Kongara Damodar、Hyun Min Lim、Jin Ho Kim、Chang-Hee Lee、Jeong Tae Lee

  DOI：10.1016/j.tet.2017.11.061

  日期：2018.1

  We successfully synthesized eight meso-aryl BODIPYs with 2,6-diethyl- or 1,2,6,7-tetraethyl substituents and characterized their photophysical properties. The steric hindrance resulting from the phenolic group in the meso-aryl moiety and the ethyl groups on the BODIPY core affected the synthesis of dipyrromethanes as an intermediate as well as the UV–Vis absorption and fluorescence emission of the

  我们成功地合成了8个具有2,6-二乙基或1,2,6,7-四乙基取代基的内消旋芳基BODIPY，并表征了它们的光物理性质。由内消旋芳基部分中的酚基和BODIPY核心上的乙基引起的空间位阻影响了作为中间体的二吡咯甲烷的合成以及BODIPY的UV-Vis吸收和荧光发射，这是由于芳基环。pH依赖性荧光发射也显示出内消旋-羟基苯基BODIPY作为pH传感器的潜在用途。
• Solvent-dependent dual-mode photochromism between T- and P-types in a dipyrrinone derivative
  作者：Yoko Sakata、Satomi Fukushima、Shigehisa Akine、Jun-ichiro Setsune

  DOI：10.1039/c5cc07625k

  日期：——

  A dipyrrinone derivative exhibited solvent-dependent dual-mode photochromism between the thermally reversible T-type (in chloroform) and the thermally irreversible P-type (in methanol).

  一种二吡啉酮衍生物在溶剂依赖下表现出热可逆的T型（在氯仿中）和热不可逆的P型（在甲醇中）双模光致变色性。
• Synthesis of Porphyrin Dimers Fused with a Benzene Unit
  作者：Hidemitsu Uno、Ken-ichi Nakamoto、Kenji Kuroki、Akiko Fujimoto、Noboru Ono

  DOI：10.1002/chem.200601644

  日期：2007.7.6

  Bicyclo[2.2.2]octadiene-connected pyrrolo-porphyrins have been prepared by an inverse-type [3+1] porphyrin synthesis of a bicyclo[2.2.2]octadiene-fused dipyrrole with a tripyrrane dicarbaldehyde. Another [3+1] porphyrin synthesis of pyrrole-connected porphyrins with the same or other tripyrrane dicarbaldehydes gave bicyclo[2.2.2]octadiene-bridged diporphyrins, the central metals and/or peripheral substituents

  双环[2.2.2]辛二烯连接的吡咯并卟啉已通过反式[3 + 1]卟啉与三吡喃二卡甲醛的双环[2.2.2]辛二烯稠合的双吡咯合成而制备。吡咯连接的卟啉与相同或其他三吡喃二甲醛的另一种[3 + 1]卟啉合成产生双环[2.2.2]辛二烯桥联的二卟啉，其中心金属和/或外围取代基不同。将双环[2.2.2]辛二烯骨架热分解为苯部分，得到高纯度形式的π系统稠合的卟啉二聚体。
• Tyrosine kinase inhibitors
  申请人：Kim S. Annette

  公开号：US20060276514A1

  公开（公告）日：2006-12-07

  The present invention relates to compounds that are capable of inhibiting, modulating and/or regulating signal transduction of both receptor-type and non-receptor type tyrosine kinases. The compounds of the instant invention possess a core structure that comprises a substituted pyrrole moiety. The present invention is also related to the pharmaceutically acceptable salts, hydrates and stereoisomers of these compounds.

  本发明涉及一种能够抑制、调节和/或调控受体型和非受体型酪氨酸激酶信号传导的化合物。该即时发明的化合物具有包含取代吡咯基团的核心结构。本发明还涉及这些化合物的药学上可接受的盐、水合物和立体异构体。
• Eisner et al., Journal of the Chemical Society, 1957, p. 733,736
  作者：Eisner et al.

  DOI：——

  日期：——