3,3'-<8-Acetyl-2,7,12,18-tetramethyl-21H,23H-porphyrin-13,17-diyl>dipropionsaeure-dimethylester | 15295-25-7

• 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'-<8-Acetyl-2,7,12,18-tetramethyl-21H,23H-porphyrin-13,17-diyl>dipropionsaeure-dimethylester
• 英文别名: 4-acetyldeuteroporphyrin IX dimethyl ester；4-acetyldeuteroporphyrin-IX dimethyl ester；8-Acetyldeuteroporphyrin IX dimethyl ester；8-acetyldeuteroporphyn IX dimethyl ester；8-acetylporphyrin IX dimethyl ester；4-Acetyldeuteroporphyrindimethylester
• CAS: 15295-25-7
• 化学式: C₃₄H₃₆N₄O₅
• 分子量: 580.684
• InChiKey: YNASAYOHFATKJP-YJRSURCCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.44
• 重原子数：
  43.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  127.03
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3,3'-<8-Acetyl-2,7,12,18-tetramethyl-21H,23H-porphyrin-13,17-diyl>dipropionsaeure-dimethylester 在 sodium tetrahydroborate 、 MS 3 Angstroem 作用下， 以 甲醇 、 邻二甲苯 为溶剂， 反应 2.5h， 生成 3,3'-<(7RS,8E)-7-(Dimethylcarbamoylmethyl)-8-ethyliden-2,7,12,18-tetramethyl-7,8-dihydro-21H,23H-porphyrin-13,17-diyl>dipropionsaeure-dimethylester
  参考文献：
  名称：

  Haake, Gerold; Meier, Axel; Montforts, Franz-Peter, Liebigs Annalen der Chemie, 1992, # 4, p. 325 - 336

  摘要：

  DOI：
• 作为产物：
  描述：

  3,3'-<8-Formyl-2,7,12,18-tetramethylporphyrin-13,17-diyl>-21H,23H-dipropionsaeure-dimethylester 在 吡啶 、 sodium dichromate 作用下， 生成 3,3'-<8-Acetyl-2,7,12,18-tetramethyl-21H,23H-porphyrin-13,17-diyl>dipropionsaeure-dimethylester
  参考文献：
  名称：

  Fischer; Wecker, Hoppe-Seyler's Zeitschrift fur Physiologische Chemie, 1942, vol. 272, p. 1,11, 18

  摘要：

  DOI：

文献信息

• Substituent effects in tetrapyrrole subunit reactivity and pinacol-pinacolone rearrangements: Vic-dihydroxychlorins and vic-dihydroxybacteriochlorins
  作者：Ravindra K. Pandey、Fuu-Yau Shiau、Meden Isaac、S. Ramaprasad、Thomas J. Dougherty、Kevin M. Smith

  DOI：10.1016/s0040-4039(00)74751-4

  日期：1992.12

  presence of electron-withdrawing groups on the macrocycle, the oxidation taking place at the subunit in the quadrant opposite to the electronegative group. Migratory aptitudes in subsequent pinacol-pinacolone rearrangements of porphyrin and pheophorbide vic-dihydroxy systems are likewise dependent upon the presence of electron-withdrawing functionalities.

  卟啉中吡咯亚基OsO 4氧化的区域专一性受到大环上吸电子基团的显着影响，氧化发生在与负电基团相反的象限中的亚基上。在卟啉和脱镁叶绿的后续频哪醇-频哪酮重排洄游性向VIC -二羟基系统同样是依赖于吸电子官能团的存在。
• Syntheses of some β-substituted alkyne porphyrins related to protoporphyrin-IX
  作者：Xuqin Jiang、Kevin M. Smith

  DOI：10.1039/p19960001601

  日期：——

  β-Acetylporphyrins (e.g. 20, 35, 39) have been treated with Vilsmeier complex (POCl3–DMF) to afford β-(1-chloro-2-formylvinyl)porphyrins (23, 36, 41); with an excess of KOH in methanol these compounds were transformed into the corresponding alkynylporphyrins (17, 37, 38). The bis-alkynyl-porphyrin 17 was transformed into the corresponding hemin 25 by treatment with iron(II) chloride.

  β-乙酰卟啉（例如20、35、39 ）已用Vilsmeier络合物（POCl 3 -DMF）处理，得到β-（1-氯-2-甲酰基乙烯基）卟啉（23、36、41）；在甲醇中用过量的KOH将这些化合物转化为相应的炔基卟啉（17，37，38）。通过用氯化铁（II）处理将双炔基-卟啉17转化为相应的血红素25 。
• Regioselective syntheses of ether-linked porphyrin dimers and trimers related to photofrin-II®
  作者：Ravindra K. Pandey、Fuu-Yau Shiau、Thomas J. Dougherty、Kevin M. Smiths

  DOI：10.1016/s0040-4020(01)91025-7

  日期：1991.11

  Using isomerically pure 4-(1-hydroxyethyl)deuteroporphyrin-IX dimethyl ester 10, 2-(1-hydroxyethyl)deuteroporphyrin-IX dimethyl ester 11, 2-acetyl-4-(1-hydroxyethyl)deuteroporphyrin-IX dimethyl ester 12 and 4-acetyl-2-(1-hydroxyethyl)deuteroporphyrin-IX dimethyl ester 13 as starting materials, a series of regiochemically pure ether-linked porphyrin dimers 25–41 and trimers 42–47 related to an anticancer

  使用异构体纯的4-（1-羟乙基）次卟-IX二甲酯10，2-（1-羟乙基）次卟-IX二甲酯11 2-乙酰基-4-（1-羟乙基）次卟-IX二甲酯12和4 -乙酰基-2-（1-羟乙基）氘卟啉-IX二甲酯13作为起始原料，一系列区域化学纯的醚连接卟啉二聚体25-41和三聚体42-47合成了与一种称为Photofrin-II®的抗癌药物有关的药物。质子NMR核Overhauser增强实验和可变温度质子NMR光谱用于表征异构体。测试了其中某些化合物相对于Photofrin-II的体内光敏能力，并简要描述了初步结果。
• Synthesis of Fluorine Analogs of Protoporphyrin Potentially Useful for Diagnosis and Therapy of Cancer. IV. Synthesis of (Trifluorovinyl)vinyl- and (1-Chloro-2,2-difluorovinyl)vinyldeuteroporphyrins.
  作者：Tsuyoshi SHIGEOKA、Yasuhisa KUWAHARA、Kiyoko WATANABE、Kasuyuki SATO、Masaaki OMOTE、Akira ANDO、Itsumaro KUMADAKI

  DOI：10.1248/cpb.47.1326

  日期：——

  Trifluoro or Chlorodifluoro analogs lf protoporphyrin, the compounds in the title, were synthesized for use in the diagnosis and therapy of cancer. 3-Or 8-acetyldeuteroporphyrin dimethyl esters (2 and 3) were iodinated with iodine in the presence of potassium carbonate to the corresponding iodo compounds (5 and 6). The iodo compounds (5 and 6) were treated with bis(trifluorovinyl)zinc in the presence of tetrakis(triphenylphosphine)-palladium to give trifluorovinyl derivatives (7 and 8) in good yields.Reduction of the acetyl group of 7 and 8 with sodium borohydride afforded the corresponding hydroxyethyl derivatives (9 and 10). Compounds (9 and 10) were dehydrated with methanesulfonyl chloride and triethylamine to give (trifluorovinyl)vinyldeuteroporphyrin dimethyl esters (11 and 12).Treatment of 5 and 6 with bis(1-chloro-2, 2-difluorovinyl)zinc in the presence of tetrakis(triphenylphosphine)palladium, followed by similar reactions as above gave (1-chloro-2, 2-difluorovinyl)-vinyldeuteroporphyrin dimethyl esters (17 and 18).

  三氟或二氟氯原卟啉类似物（即标题中的化合物）被合成用于癌症的诊断和治疗。在碳酸钾存在下，3-或8-乙酰基二氢卟啉二甲酯（2和3）被碘化，得到相应的碘化合物（5和6）。在四（三苯基膦）钯存在下，碘化合物（5和6）与双（三氟乙烯基）锌反应，得到三氟乙烯基衍生物（7和8），收率较高。用硼氢化钠还原7和8的乙酰基，得到相应的羟乙基衍生物（9和10）。用甲磺酰氯和三乙胺使化合物（9和10）脱水，得到（三氟乙烯基）乙烯基二氢卟啉二甲酯（11和12）。在四（三苯基膦）钯存在下，用双（1-氯-2,2-二氟乙烯基）锌处理5和6，然后进行与上述类似的反应，得到（1-氯-2,2-二氟乙烯基）乙烯基二氢卟啉二甲酯（17和18）。
• 3,8-Diethynyl-3,8-devinylprotoporphyrin IX dimethyl ester and its haemin
  作者：Xuqin Jiang、Kevin M. Smith

  DOI：10.1039/c39930001054

  日期：——

  Treatment of 3,8-diacetyldeuteroporphyrin IX dimethyl ester 6 with phosphoryl chloride and N,N-dimethylformamide gives the 3,8-bis(1-chloro-2-formylvinyl) derivative 7 which affords the corresponding 3,8-diethynyl derivative 2 upon treatment with base; compound 2 and its iron(III) chloride dimethyl ester are fully characterized.

  用磷酰氯和N，N-二甲基甲酰胺处理3,8-二乙酰基氘卟啉IX二甲酯6，得到3,8-双（1-氯-2-甲酰基乙烯基）衍生物7，其在反应后得到相应的3,8-二乙炔基衍生物2。用碱处理；充分表征了化合物2及其氯化铁（III）二甲基酯。