dibenzyl 3,3'-diethyl-4,4'-dimethyldipyrromethane-5,5'-dicarboxylate | 7670-40-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: dibenzyl 3,3'-diethyl-4,4'-dimethyldipyrromethane-5,5'-dicarboxylate
• 英文别名: Dibenzyl 3,3'-diethyl-4,4'-dimethyl-2,2'-dipyrrylmethane-5,5'-dicarboxylate；dibenzyl 3,3'-diethyl-4,4'-dimethylpyrromethane-5,5'-dicarboxylate；5,5'-bis(benzyloxycarbonyl)-3,3'-diethyl-4,4'-dimethyl-2,2'-dipyrrylmethane；5,5'-bis(benzyloxycarbonyl-4,4'-dimethyl-3,3'-diethyl-2,2'-dipyrrolyl)methane；5,5’-bis(benzyloxycarbonyl)-3,3’-diethyl-4,4’dimethyl-2,2’-dipyrrylmethane；3,3'-Diethyl-4,4'-dimethyl-2,2'-pyrromethan-5,5'-dicarbonsaeure-dibenzylester；dibenzyl 3,3'-diethyl-4,4-dimethyl-2,2'-dipyrromethane-5,5'-dicarboxylate；Dibenzyl-3,3'-diethyl-4,4'-dimethyldipyrromethan-5,5'-dicarboxylat；Bis-(3-Ethyl-5-benzyloxycarbonyl-4-methyl-2-pyrrolyl)-methan；4,4'-diethyl-3,3'-dimethyl-1H,1'H-5,5'-methanediyl-bis-pyrrole-2-carboxylic acid dibenzyl ester；4,4'-Diaethyl-3,3'-dimethyl-5,5'-methandiyl-bis-pyrrol-2-carbonsaeure-dibenzylester；4,4'-Dimethyl-3,3'-diethyl-5,5'-carbobenzyloxy-dipyrromethan；Dibenzyl 3,3'-diethyl-4,4'-dimethyl-2,2'-methylenebis(pyrrole-5-carboxylate)；benzyl 4-ethyl-5-[(3-ethyl-4-methyl-5-phenylmethoxycarbonyl-1H-pyrrol-2-yl)methyl]-3-methyl-1H-pyrrole-2-carboxylate
• CAS: 7670-40-8
• 化学式: C₃₁H₃₄N₂O₄
• 分子量: 498.622
• InChiKey: PEMZHJXFRVUICU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  84.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dibenzyl 3,3'-diethyl-4,4'-dimethyldipyrromethane-5,5'-dicarboxylate 在 palladium on activated charcoal 氢气 、 苯甲酰氯 作用下， 以 乙酸乙酯 为溶剂， 反应 22.75h， 生成 4,4'-diethyl-3,3'-dimethyl-5,5'-methanediyl-bis-pyrrole-2-carbaldehyde
  参考文献：
  名称：

  具有聚苯撑基的双卟啉供体-受体化合物中的电子转移显示出弱的距离依赖性

  摘要：

  已经合成了一系列亚苯基桥连的双卟啉加合物，包含一个、两个或三个苯桥。提供了完整的合成细节。为了研究光化学电子转移，加入了混合金属，锌在一个卟啉大环中，而 Fe III（双咪唑）在另一个大环中。当光激发时，一个电子从 Zn 转移到 Fe III

  DOI：

  10.1021/ja00041a047
• 作为产物：
  描述：

  乙酰丙酮苄酯 在 lead(IV) acetate 、 盐酸 、 sodium nitrate 、 sodium acetate 、 溶剂黄146 、 锌 作用下， 以 乙醇 、 水 为溶剂， 反应 4.0h， 生成 dibenzyl 3,3'-diethyl-4,4'-dimethyldipyrromethane-5,5'-dicarboxylate
  参考文献：
  名称：

  具有聚苯撑基的双卟啉供体-受体化合物中的电子转移显示出弱的距离依赖性

  摘要：

  已经合成了一系列亚苯基桥连的双卟啉加合物，包含一个、两个或三个苯桥。提供了完整的合成细节。为了研究光化学电子转移，加入了混合金属，锌在一个卟啉大环中，而 Fe III（双咪唑）在另一个大环中。当光激发时，一个电子从 Zn 转移到 Fe III

  DOI：

  10.1021/ja00041a047

文献信息

• Electron transfer in bis-porphyrin donor-acceptor compounds with polyphenylene spacers shows a weak distance dependence
  作者：Anna Helms、David Heiler、George McLendon

  DOI：10.1021/ja00041a047

  日期：1992.7

  containing one, two, or three phenyl bridges. Complete synthetic details are provided. For studies of photochemical electron transfer, mixed metals were incorporated, with zinc in one porphyrin macrocycle and Fe III (bis-imidazole) in the other macrocycle. When photoexcited, an electron is transferred from Zn to Fe III

  已经合成了一系列亚苯基桥连的双卟啉加合物，包含一个、两个或三个苯桥。提供了完整的合成细节。为了研究光化学电子转移，加入了混合金属，锌在一个卟啉大环中，而 Fe III（双咪唑）在另一个大环中。当光激发时，一个电子从 Zn 转移到 Fe III
• Synthesis and photophysical properties of porphyrins containing viologen units for ultrafast molecular photonics
  作者：Robert Laudien、Iori Yoshida、Toshihiko Nagamura

  DOI：10.1039/b202991j

  日期：——

  Several 5,15-diarylporphyrin derivatives containing viologen units as an electron acceptor for ultrafast intramolecular electron transfer have been synthesized. The fluorescence of the porphyrin–viologen linked systems was appreciably quenched by the attached viologens. In accordance with this, the formation of a charge-separated state was observed upon excitation with a femtosecond (fs) laser at 400 nm. The rate of electron transfer and back transfer was controlled by the different length of alkyl chain spacers between porphyrin and viologen. Attempts to use these porphyrin molecules as a thin film component of ultrafast parallel data processing by guided wave mode geometry were limited by gradual deterioration upon repeated fs laser excitation.

  合成了几种含有紫精单元作为电子受体的5,15-二芳基卟啉衍生物，用于超快分子内电子转移。连接的紫精单元显著淬灭了卟啉-紫精体系的荧光。与此一致，在400 nm飞秒激光激发下观察到电荷分离态的形成。电子转移和逆转移的速率受控于卟啉和紫精之间不同长度的烷基链间隔物。试图将这些卟啉分子用作通过波导模式几何结构的薄膜组件，用于超快并行数据处理，但由于反复飞秒激光激发导致的逐渐退化而受到限制。
• Polypyrroles as Antioxidants:  Kinetic Studies on Reactions of Bilirubin and Biliverdin Dimethyl Esters and Synthetic Model Compounds with Peroxyl Radicals in Solution. Chemical Calculations on Selected Typical Structures
  作者：Leonid L. Chepelev、Cory S. Beshara、Patricia D. MacLean、Gillian L. Hatfield、Amy A. Rand、Alison Thompson、James S. Wright、L. Ross C. Barclay

  DOI：10.1021/jo051359e

  日期：2006.1.1

  Rate constants for hydrogen-atom transfer (HAT) from bilirubin dimethyl ester (BRDE) and biliverdin dimethyl ester (BVDE) to peroxyl radicals during inhibited autoxidation of styrene initiated by azo-bisisobutyronitrile (AIBN) were kinh(BRDE) = 22.5 × 104 and kinh(BVDE) = 10.2 × 104 M-1 s-1, and the stoichiometric factors (n) were 2.0 and 2.7, respectively. A synthetic tetrapyrrole (bis(dipyrromethene))

  在偶氮-双异丁腈（AIBN）引发的苯乙烯自抑制氧化过程中，氢胆素从胆红素二甲基酯（BRDE）和胆绿素二甲酯（BVDE）到过氧自由基的转移速率常数为k inh（BRDE）= 22.5×10 4和k inh（BVDE）= 10.2×10 4 M - 1 s - 1，化学计量系数（n）分别为2.0和2.7。合成四吡咯含有（双（二吡咯亚甲基））α -中央（2,2' ）CH 2联动给ķ INH = 39.9×10 4中号-1 s - 1，n = 2.3，而β-连接的（3,3'）异构体不是活性抗氧化剂。合成了几个二吡啶酮，作为胆红素和胆绿素的两个外杂环的模拟物。在每个环中含有NH基的二吡啶酮是活性抗氧化剂，而缺乏两个这样的“游离” NH基的二吡啶酮（如N-CH 3吡啶酮和二嘧啶）则没有抗氧化活性。总的来说，相对ķ INH值相比，这些酚类抗氧化剂，2,6-二-叔丁基-4-甲氧基苯酚（DBHA）和2,6-二-叔丁基-4-甲基苯酚（BHT）是2
• Fluorinated photosensitizers: synthesis, photophysical, electrochemical, intracellular localization, in vitro photosensitizing efficacy and determination of tumor-uptake by 19F in vivo NMR spectroscopy
  作者：Suresh K Pandey、Amy L Gryshuk、Andrew Graham、Kei Ohkubo、Shunichi Fukuzumi、Mahabeer P Dobhal、Gang Zheng、Zhongping Ou、Riqiang Zhan、Karl M Kadish、Allan Oseroff、S Ramaprasad、Ravindra K Pandey

  DOI：10.1016/j.tet.2003.10.016

  日期：2003.12

  starting from pyrroles, a series of fluorinated porphyrins were synthesized by following the MacDonald reaction conditions. Upon reaction with osmium tetroxide, a fluorinated porphyrin containing four trifluoromethyl groups (12 fluorine units) was converted into the related chlorin and bacteriochlorin which exhibited long-wavelength absorptions at 652 and 720 nm, respectively. All compounds produced good

  对于体内NMR研究，从吡咯开始，通过遵循MacDonald反应条件，合成了一系列氟化卟啉。与四氧化反应后，含四个三氟甲基（12个氟单元）的氟化卟啉被转化为相关的二氢卟酚和细菌二氢卟酚，它们分别在652和720 nm处表现出长波吸收。所有化合物均产生了良好的单线态氧生产效率。对具有和不具有氟取代基的九种卟啉的比较研究表明，氟化基团的存在对卟啉，二氢卟酚或细菌二氢卟啉的光物理性质没有不利影响。研究的化合物的第一和第二单电子还原电位（vs SCE）介于-1.29和-1.49 V之间和-1.66和-1之间。PhCN中84 V含0.1 M TBAP。紫外可见光谱电化学数据表明，在第一次还原和第一次氧化后，会形成π阴离子和π阳离子自由基。体内19 F MR对具有十二个当量氟的代表性氟标记化合物的19 F MR研究证实，通过在小鼠足背上植入2×10 5个细胞，在小鼠（C3H / HeJ）中植入了氟标记的敏化剂（C3H
• Synthetic and biosynthetic studies of porphyrins. Part 9. Synthesis of isocoproporphyrin, dehydroisocoproporphyrin, and de-ethylisocoproporphyrin
  作者：Anthony H. Jackson、Timothy D. Lash、David J. Ryder

  DOI：10.1039/p19870000287

  日期：——

  The title compounds, which were excreted by patients suffering from porphyria cutanea tarda or rats poisoned with hexachlorobenzene have been synthesized by the b-oxobilane route. Isocoproporphyrin tetramethyl ester (7a) was prepared from pyrromethanes corresponding to rings DA and BC of the macrocycle, and the de-ethyl analogue (7b) was prepared in a similar fashion; acetylation of the latter followed

  标题化合物，其通过从皮肤卟啉症或迟发性与六氯苯中毒大鼠的患者排出已经由合成b -oxobilane路线。由对应于大环的DA和BC环的吡咯甲烷制备异卟啉四甲酯（7a），以类似方式制备脱乙基类似物（7b）。后者的乙酰化，然后还原和脱水，然后得到脱氢异卟啉四甲基酯（7d）。合成中产生的少量副产物已显示是通过BC吡咯甲烷的重排而产生的。