3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester | 5522-66-7

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四吡咯及其衍生物
• 英文名称: 3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester
• 英文别名: protoporphyrin IX dimethyl ester；protoporphyrin dimethyl ester
• CAS: 5522-66-7
• 化学式: C₃₆H₃₈N₄O₄
• 分子量: 590.722
• InChiKey: WASRLAPXOHTNAX-MFBGAUBSSA-N

物化性质

• 熔点：
  225-228 °C(lit.)
• 沸点：
  1017.0±65.0 °C(Predicted)
• 密度：
  1.220±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于DMSO

计算性质

• 辛醇/水分配系数(LogP)：
  7.68
• 重原子数：
  44.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  109.96
• 氢给体数：
  2.0
• 氢受体数：
  6.0

制备方法与用途

化学性质

原卟啉 IX 二甲酯呈深紫色粉末状，溶解性：溶于DMSO，丙酮，氯仿。

反应信息

• 作为反应物：
  描述：

  3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester 以 乙醚 、 二氯甲烷 、 邻二氯苯 为溶剂， 反应 96.33h， 生成 3,8-dicyclopropyldeuteroporphyrin IX dimethyl ester
  参考文献：
  名称：

  Pyrazolinyl and cyclopropyl derivatives of protoporphyrin IX and chlorins related to chlorophyll a

  摘要：

  Diazomethane reacts regioselectively with peripheral vinyl substituents of pyropheophorbide a and purpurin-18 N-methylimide to produce corresponding 1'-pyrazolinyl-substituted derivatives as a main product. Similarly, treatment of protoporphyrin IX gave a mixture of mono- and di-substituted pyrazolinyl analogs, which were isolated as individual products. Thermolytic decomposition of the pyrazolinyl derivatives produced cyclopropyl-substituted chlorins and porphyrins. 1,3-Dipolar cycloaddition mechanisms of the formation of 1'-pyrazolinyl derivatives are discussed. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01525-9
• 作为产物：
  描述：

  benzyl 4-acetyl-3,5-dimethylpyrrole-2-carboxylate 在 氢氧化钾 、 sodium tetrahydroborate 、 三氟化硼乙醚 、 氢溴酸 、 溴 、 碘 、 苯甲酰氯 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 四氯化碳 、 乙醚 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.51h， 生成 3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester
  参考文献：
  名称：

  Mironov, A. F.; Nizhnik, A. N.; Kozhich, D. T., Journal of general chemistry of the USSR, 1981, vol. 51, # 3, p. 565 - 571

  摘要：

  DOI：

文献信息

• Design and synthesis of protoporphyrin IX/vitamin<font>B₁₂</font>molecular hybrids<i>via</i><font>CuAAC</font>reaction
  作者：Rafał Loska、Anita Janiga、Dorota Gryko

  DOI：10.1142/s1088424612501350

  日期：2013.1

  The design and synthesis of new molecular hybrids composed of protoporphyrin IX (PPIX) and vitamin B₁₂via copper catalyzed alkyne azide cycloaddition reaction is described. New, clickable aminoazide and aminoalkyne linkers were prepared and subsequently attached to PPIX (via vinyl group) and to vitamin B₁₂giving desired building blocks. Preliminary results showed that respective water soluble hybrids were formed under CuAAC reaction. Gratifyingly, Cu incorporation into the PPIX core was avoided, which was important for further biological studies.

  本文介绍了通过铜催化炔吖啶环加成反应设计和合成由原卟啉 IX（PPIX）和维生素 B12 组成的新分子杂化物。研究人员制备了新的、可点击的氨基吖啶和氨基炔连接体，随后将其连接到 PPIX（通过乙烯基）和维生素 B12 上，得到了所需的构建模块。初步结果表明，在 CuAAC 反应中形成了各自的水溶性混合物。令人欣慰的是，Cu 并入 PPIX 核心的情况得以避免，这对进一步的生物研究非常重要。
• Process For Preparing Porphyrin Derivatives, Such As Protoporphyrin (IX) And Synthesis Intermediates
  申请人：Martin Pierre

  公开号：US20080242857A1

  公开（公告）日：2008-10-02

  The present invention relates to a process for preparing a porphyrin of formula (I), optionally in the form of a salt with an alkali metal and/or in the form of a metal complex: in which: R and R′ are as defined in claim 1 , comprising: a step of condensation, in an acidic medium, between a dipyrromethane of formula (II): in which R′b is as defined above for (I), and a dipyrromethane of formula (III): in which R″ is as defined in claim 1 , and also the compounds of formula (III).

  本发明涉及一种制备公式（I）的卟啉的方法，可选地以碱金属的盐形式和/或金属配合物的形式存在： 其中： R和R′如权利要求1中定义的那样， 包括： 在酸性介质中，通过公式（II）的二吡咯甲烷和公式（III）的二吡咯甲烷之间的缩合步骤： 其中R′b如上述（I）中定义的那样， 以及公式（III）的化合物。
• METHOD FOR PREPARING A BIOCIDAL, BACTERIOCIDAL AND/OR BACTERIOSTATIC MATERIAL
  申请人：COMMISSARIAT À L'ÉNERGIE ATOMIQUE ET AUX ÉNERGIES ALTERNATIVES (CEA)

  公开号：US20220053766A1

  公开（公告）日：2022-02-24

  A process for preparing a biocidal, bactericidal and/or bacteriostatic material including the preparation of a polymer precursor solution that has (a) at least one monomer A having a porphyrin group and at least one radical polymerizable function, (b) at least one radical polymerizable monomer B, a photoinitiator, and (c) at least one of the monomers chosen from a monomer C having a quaternary amine and a radical polymerizable function; and/or a monomer D having copper and a radical polymerizable function. Also, the material obtainable by the process and its uses.

  一种制备生物杀菌、杀菌和/或抑菌材料的方法，包括制备具有（a）至少一种具有卟啉基团和至少一种自由基聚合功能的单体A的聚合物前体溶液，（b）至少一种自由基聚合单体B，光引发剂，以及（c）至少一种从具有季铵盐基团和自由基聚合功能的单体C中选择的单体; 和/或具有铜和自由基聚合功能的单体D。此外，还包括所述方法获得的材料及其用途。
• COMPOSITIONS, APPARATUS, SYSTEMS, AND METHODS FOR RESOLVING ELECTRONIC EXCITED STATES
  申请人：HALLSTAR INNOVATIONS CORP.

  公开号：US20140044654A1

  公开（公告）日：2014-02-13

  The present disclosure relates, according to some embodiments, to molecules, including conjugated fused polycyclic molecules, that may receive excited state energy from other molecules (e.g., light-absorbing molecules) or directly from the irradiation sources. According to some embodiments, the disclosure relates to molecules, including conjugated fused polycyclic molecules, that may resolve (e.g., quench, dissipate) excited state energy, normally by way of releasing it as heat. (e.g., as heat). Conjugated fused polycyclic molecules of various structures are disclosed including Formula III: The disclosure further relates to methods of use and/or therapy using molecules of Formulas I, II, and/or III.

  本公开涉及一些实施例，涉及分子，包括共轭融合多环分子，这些分子可以从其他分子（例如吸收光的分子）或直接从辐射源接收激发态能量。根据一些实施例，本公开涉及分子，包括共轭融合多环分子，这些分子可以通过释放为热量的方式解决（例如，熄灭，耗散）激发态能量。披露了具有各种结构的共轭融合多环分子，包括式III。本公开还涉及使用式I、II和/或III的分子进行治疗和/或疗法的方法。
• Facile iodination of the vinyl groups in protoporphyrin IX dimethyl ester and subsequent transformation of the iodinated moieties
  作者：Kota Miyata、Satoru Yasuda、Takuto Masuya、Satoshi Ito、Yusuke Kinoshita、Hitoshi Tamiaki、Toru Oba

  DOI：10.1016/j.tet.2018.05.040

  日期：2018.7

  positions of methyl pyropheophorbide-a bearing a chlorin π-system, a chlorophyll-a derivative, was modified with PIFA and I2. The reaction intermediates derived from the porphyrin were more reactive than those from the chlorin and liable to form intermolecular linkages. The obtained 2-iodo-1-hydroxyethyl group was transformed into a formyl group by a mild treatment. The corresponding iodoether moiety was

  研究了使用苯基碘双（三氟乙酸盐）（PIFA）和I 2对原卟啉IX二甲酯进行碘化。碘同等地加到C3-和C8-乙烯基上，分别在水或醇存在下提供碘醇或碘醚。任何内消旋α-氢原子没有被在这些条件下，碘原子取代的，尽管这两个乙烯基和一个内消旋甲基的pyropheophorbide-位置一个轴承二氢卟酚的π系统，叶绿素一个衍生物，用PIFA和改性我2。来源于卟啉的反应中间体比来自二氢卟酚的反应中间体反应性更高，并且易于形成分子间键。通过温和的处理，将获得的2-碘-1-羟乙基转化为甲酰基。在碱性条件下，相应的碘醚部分易于转化为乙酰基。这些转变也适用于较小的烯烃，例如苯乙烯。