六氢卟吩 | 4396-11-6

• 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
• 中文名称: 六氢卟吩
• 英文名称: 5H,10H,15H,20H,22H,24H-porphyrin
• 英文别名: calix[4]pyrrole；porphyrinogen；hexahydroporphine；5,10,15,20,21,22,23,24-octahydroporphyrin
• CAS: 4396-11-6
• 化学式: C₂₀H₂₀N₄
• 分子量: 316.406
• InChiKey: VCRBUDCZLSQJPZ-UHFFFAOYSA-N

物化性质

• 沸点：
  671.5±50.0 °C(Predicted)
• 密度：
  1.289±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  63.2
• 氢给体数：
  4
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  六氢卟吩 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.5h， 生成 porphyrin
  参考文献：
  名称：

  Porphyrin Synthesis in Surfactant Solution:  Multicomponent Assembly in Micelles

  摘要：

  A synthesis of meso-substituted porphyrins in anionic sodium dodecyl sulfate micelles has been developed. Polar, functionalized aromatic aldehydes condense reversibly with pyrrole in the micellar phase. Oxidation of the porphyrinogen then provides functionalized porphyrins in yields of 10-48%. Hydrophobic aldehydes condense irreversibly to give low yields at practical substrate concentrations. Synthesis in D2O solution results in per-beta-deuterated porphyrins. A two-phase model is used to rationalize the dependence of porphyrin yield on reactant and surfactant concentration. Micelles are viewed as potential wells which promote porphyrinogen assembly by binding products more tightly than reactants.

  DOI：

  10.1021/jo9600161
• 作为产物：
  描述：

  2,2'-二吡咯基甲烷 在 sodium tetrahydroborate 、 溶剂黄146 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 8.17h， 生成 六氢卟吩
  参考文献：
  名称：

  通过还原杂芳基化合成双吲哚基甲烷、双吡咯基甲烷和吲哚基吡咯基甲烷衍生物

  摘要：

  已开发出一种用于合成双吲哚基甲烷、双吡咯基甲烷和吲哚基吡咯基甲烷衍生物的有效且通用的还原性杂芳基化方法。因此，在硼氢化钠和乙酸的组合存在下用吲哚或吡咯处理酰基吡咯或酰基吲哚衍生物导致以中等至极好的分离产率形成标题化合物。

  DOI：

  10.1016/j.tet.2021.132338

文献信息

• Methods and intermediates for the synthesis of porphyrins
  申请人：Lindsey S. Jonathan

  公开号：US20070027312A1

  公开（公告）日：2007-02-01

  A method of making a porphyrin (I) is carried out by condensing (i) a bis(imino)dipyrromethane of Formula II: with (ii) a dipyrromethaneto produce a reaction product; then (b) optionally oxidizing said reaction product with an oxidizing agent; and then (c) optionally demetallating said reaction product to produce the porphyrin. Methods of making compounds of Formula II are also described.

  一种制备卟啉（I）的方法是通过将公式II的双（亚亚胺）二吡咯甲烷（i）与二吡咯甲烷（ii）进行缩合反应以产生反应产物；然后（b）可选择地使用氧化剂氧化所述反应产物；然后（c）可选择地去金属化所述反应产物以产生卟啉。还描述了制备公式II化合物的方法。
• CARBORANYLPORPHYRINS AND USES THEREOF
  申请人：Wu Haitao

  公开号：US20050287073A1

  公开（公告）日：2005-12-29

  The present invention is directed to low toxicity boronated compounds and methods for their use in the treatment, visualization, and diagnosis of tumors. More specifically, the present invention is directed to low toxicity carborane-containing 5,10,15,20-tetraphenylporphyrin compounds and methods for their use particularly in boron neutron capture therapy (BNCT) and photodynamic therapy (PDT) for the treatment of tumors of the brain, head, neck, and surrounding tissue. The invention is also directed to using these carborane-containing tetraphenyl porphyrin compounds to methods of tumor imaging and/or diagnosis such as MRI, SPECT, or PET.

  本发明涉及低毒性硼化合物及其在肿瘤治疗、可视化和诊断中的应用方法。更具体地说，本发明涉及低毒性的含有碳硼烷的5,10,15,20-四苯基卟啉化合物，以及它们在脑部、头部、颈部和周围组织肿瘤治疗中的应用方法，特别是硼中子俘获疗法（BNCT）和光动力疗法（PDT）。该发明还涉及使用这些含有碳硼烷的四苯基卟啉化合物进行肿瘤成像和/或诊断的方法，例如MRI、SPECT或PET。
• METHODS AND COMPOSITIONS COMPRISING MACROCYCLES
  申请人：Nocera Daniel G.

  公开号：US20110144324A1

  公开（公告）日：2011-06-16

  The present invention relates generally to methods and compositions comprising macrocycles. In some embodiments, the present invention provides methods for modifying macrocycles comprising a pendant group. In some cases, the pendent group comprises a hydrolyzable group. The present invention also provides methods for metallating a macrocycle using microwave energy, in some embodiments.

  本发明通常涉及包含大环的方法和组合物。在某些实施方式中，本发明提供了用于修改具有挂链基团的大环的方法。在某些情况下，挂链基团包括可水解基团。本发明还提供了在某些实施方式中使用微波能量对大环进行金属化的方法。
• Metal complexation of 1-acyldipyrromethanes and porphyrins formed therefrom
  申请人：Lindsey S. Jonathan

  公开号：US20060142562A1

  公开（公告）日：2006-06-29

  A first aspect of the invention is a method of making a porphyrin-metal complex, comprising: (a) providing a first reagent selected from the group consisting of 1-acyldipyrromethanes, 1-acyldipyrrins, dipyrromethane-1-carbinols 1,9-diacyldipyrromethanes and 1,9-diacyldipyrrins; and then (b) condensing the first reagent with either itself (in the case of 1-acyldipyrromethanes, 1-acyldipyrrins, and dipyrromethane-1-carbinols) or a dipyrromethane (in the case of 1,9-diacyldipyrromethanes and 1,9-diacyldipyrrins) in a reaction mixture comprising a solvent and a second reagent selected from the group consisting of palladium and copper complexes to produce the porphyrin-metal complex (with the metal being palladium or copper). In preferred embodiments of the foregoing, the reaction mixture further comprises a base such as KOH or NaH.

  本发明的第一个方面是一种制备卟啉金属配合物的方法，包括：(a)提供选自1-酰基二吡咯甲烷、1-酰基二吡咯、二吡咯甲烷-1-甲醇、1,9-二酰基二吡咯甲烷和1,9-二酰基二吡咯的第一试剂；然后(b)将第一试剂与溶剂和选自钯和铜配合物的第二试剂在反应混合物中缩合，以产生卟啉金属配合物（金属为钯或铜）。在上述中的优选实施方案中，反应混合物进一步包括碱，如KOH或NaH。
• Glycosylated Carboranylporphyrins and Uses Thereof
  申请人：Miura Michiko

  公开号：US20080279781A1

  公开（公告）日：2008-11-13

  The present invention is directed to low toxicity boronated compounds and methods for their use in the treatment, visualization, and diagnosis of tumors. More specifically, the present invention is directed to low toxicity glycosylated carborane-containing 5,10,15,20-tetraphenylporphyrin compounds and methods for their use particularly in boron neutron capture therapy (BNCT) and photodynamic therapy (PDT) for the treatment of tumors of the brain, and head and neck. The invention is also directed to using these glycosylated carborane-containing tetraphenylporphyrin compounds in methods of tumor imaging and/or diagnosis such as MRI, SPECT, or PET.

  本发明涉及低毒性硼化合物及其在肿瘤治疗、可视化和诊断中的使用方法。更具体地说，本发明涉及低毒性糖基化的含有5,10,15,20-四苯基卟啉的碳硼烷化合物及其在硼中子俘获治疗（BNCT）和光动力疗法（PDT）中的使用方法，特别用于治疗脑部、头颈部肿瘤。该发明还涉及使用这些糖基化的碳硼烷化合物在肿瘤成像和/或诊断方法中的应用，如MRI、SPECT或PET。