5-(6-Hydroxy-2-pivaloyloxyphenyl)-10,15,20-tris<2,6-bis(pivaloyloxy)phenyl>porphyrin | 130203-62-2

• 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: 5-(6-Hydroxy-2-pivaloyloxyphenyl)-10,15,20-tris<2,6-bis(pivaloyloxy)phenyl>porphyrin
• 英文别名: 5,10,15-tri(2',6'-bis(pivaloyloxy)phenyl)-20-((2'-hydroxy-6'-pivaloyloxy)phenyl)porphine
• CAS: 130203-62-2
• 化学式: C₇₉H₈₆N₄O₁₅
• 分子量: 1331.57
• InChiKey: VOKXFJUJYITCKL-GKFNADBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.69
• 重原子数：
  98.0
• 可旋转键数：
  11.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  261.69
• 氢给体数：
  3.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  5-(6-Hydroxy-2-pivaloyloxyphenyl)-10,15,20-tris<2,6-bis(pivaloyloxy)phenyl>porphyrin 、 5-Imidazol-1-yl-pentanoyl chloride; hydrochloride 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 6.0h， 生成 5-<2-(5-Imidazolylvaleryloxy)-6-(pivaloyloxy)phenyl>-10,15,20-tris<2,6-bis(pivaloyloxy)phenyl>porphyrin
  参考文献：
  名称：

  Synthesis and dioxygen-binding properties of double-sided porphyrinatoiron(II) complexes bearing covalently bound axial imidazole

  摘要：

  Double-sided porphyrinatoiron(II) complexes bearing covalently bound axial imidazole, 5-[2-(5-imidazolylvaleryloxy)-6-(pivaloyloxy)phenyl]-10,15,20-tris[2,6-bis(pivaloyloxy)phenyl]porphyrinato-iron(II) and 5-[2-(3,3-dimethylbutyryloxy)-6-(5-imidazolylvaleryloxy)phenyl]-10,15,20-tris[2,6-bis(3,3-dimethylbutyryloxy)phenyl]porphyrinatoiron(II), have been synthesized. On the basis of their absorption and H-1 NMR spectra, the axial imidazole group is co-ordinated. The complexes reversibly form stable dioxygen adducts in toluene at 25-degrees-C, and the kinetics of binding of 02 and CO has been investigated. When embedded in phospholipid unilamellar vesicles, the complexes possess the ability to transport dioxygen in an aqueous medium. The binding affinity of the pivaloyloxy derivative [P1/2(O2) = 27 Torr] is equal to that of a red blood cell suspension and the half-life of the dioxygen adduct formed was 1.5 d under physiological conditions (pH 7.4, 37-degrees-C).

  DOI：

  10.1039/dt9930002465
• 作为产物：
  描述：

  三甲基乙酰氯 、 5,10,15,20-tetrakis(2,6-bis(hydroxy)phenyl)porphyrin 在 4-二甲氨基吡啶 作用下， 以 四氢呋喃 为溶剂， 以9.3%的产率得到5-(6-Hydroxy-2-pivaloyloxyphenyl)-10,15,20-tris<2,6-bis(pivaloyloxy)phenyl>porphyrin
  参考文献：
  名称：

  新型双面卟啉 (II) 复合物的合成和配位行为：咪唑口袋大小对分子氧结合的影响

  摘要：

  描述了新的“双侧卟啉 (II) 复合物”的合成和特征连接行为，该复合物在环平面的每一侧具有两个不同间距大小的口袋，在大环的两侧具有较大尺寸的口袋。咪唑衍生物与四配位卟啉化铁 (II) 的平衡常数与口袋空间的大小成比例增加，这由 ΔH 项反映。通过在甲苯溶液中加入 1,2-二甲基-咪唑 (1,2-dmin) 获得的卟啉化合物的五配位配合物在 25°C 下形成稳定且可逆的分子氧加合物。随着卟啉平面后侧的空间位阻减小，铁 (II) 配合物的氧亲和力增加。

  DOI：

  10.1246/bcsj.64.888

文献信息

• A Bis-Fenced Porphinatoiron Having Seven Pivaloyloxy Groups on the Porphyrin Ring Plane. Synthesis and Ligand Binding
  作者：Eishun Tsuchida、Etsuo Hasegawa、Teruyuki Komatsu、Keisuke Nakao、Hiroyuki Nishide

  DOI：10.1246/cl.1990.1071

  日期：1990.7

  tetraphenylporphyrin derivative having two pockets on both sides of the porphyrin ring plane, 5,10,15-tri(2′,6′-bis(pivaloyloxy)phenyl)-20-((2′-hydroxy-6′-pivaloyloxy)phenyl)porphine, and its iron complex were synthesized. The 1,2-dimethylimidazole binding to the iron(II) was enhanced by the presence of a steric-hindrance reduced pocket. The complex formed a stable dioxygen adduct in toluene at 25°C.

  一种在卟啉环平面两侧具有两个口袋的新型四苯基卟啉衍生物，5,10,15-三(2',6'-双(新戊酰氧基)苯基)-20-((2'-羟基-6'-新戊酰氧基)苯基)卟啉及其铁配合物的合成。1,2-二甲基咪唑与铁（II）的结合因空间位阻减少的口袋的存在而增强。该配合物在 25°C 的甲苯中形成稳定的双氧加合物。
• Tsuchida, Eishun; Komatsu, Teruyuki; Arai, Kenji, Journal of the Chemical Society, Dalton Transactions
  作者：Tsuchida, Eishun、Komatsu, Teruyuki、Arai, Kenji、Nishide, Hiroyuki

  DOI：——

  日期：——