zinc(II) methylpyropheophorbide a | 82352-22-5

• 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: zinc(II) methylpyropheophorbide a
• 英文别名: zinc methyl pyropheophorbide a；zinc;16-ethenyl-11-ethyl-22-(3-methoxy-3-oxopropyl)-12,17,21,26-tetramethyl-23,24,25-triaza-7-azanidahexacyclo[18.2.1.15,8.110,13.115,18.02,6]hexacosa-1(23),2(6),4,8(26),9,11,13(25),14,16,18(24),19-undecaen-4-olate
• CAS: 82352-22-5；125409-36-1
• 化学式: C₃₄H₃₄N₄O₃Zn
• 分子量: 612.059
• InChiKey: PJOXMWQSNVTNQJ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  6.75
• 重原子数：
  42
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  70.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  zinc(II) methylpyropheophorbide a 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 丙酮 为溶剂， 反应 0.08h， 生成 zinc methyl protopyropheophorbide a
  参考文献：
  名称：

  Comparison of demetalation properties between zinc chlorin and zinc porphyrin derivatives: Effect of macrocyclic structures

  摘要：

  Metalloporphyrins and metallochlorins are important biological molecules in nature. To examine the effect of macrocyclic structures on removal of central metals from these cyclic tetrapyrrole molecules without peripheral substitution effects, demetalation of zinc methyl pyropheophorbide a (zinc chlorin 1) and zinc methyl protopyropheophorbide a (zinc porphyrin 2) was kinetically analyzed under acidic conditions. Both 1 and 2 exhibited gradual spectral changes from zinc complexes to free-base forms with several isosbectic points in acetone/water (10: 1) at the proton concentration of 6.1 x 10(-3) M. Demetalation of zinc porphyrin 2 was slower than that of zinc chlorin 1 in the temperature range between 15 and 35 degrees C. This indicates that the porphyrin macrocycle provides tolerance to removal of the central metal from cyclic tetrapyrrole ligands compared with the chlorin macrocycle. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.019
• 作为产物：
  描述：

  Methyl-pyrophaeophorbid a 在 zinc(II) acetate dihydrate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 zinc(II) methylpyropheophorbide a
  参考文献：
  名称：

  Comparison of demetalation properties between zinc chlorin and zinc porphyrin derivatives: Effect of macrocyclic structures

  摘要：

  Metalloporphyrins and metallochlorins are important biological molecules in nature. To examine the effect of macrocyclic structures on removal of central metals from these cyclic tetrapyrrole molecules without peripheral substitution effects, demetalation of zinc methyl pyropheophorbide a (zinc chlorin 1) and zinc methyl protopyropheophorbide a (zinc porphyrin 2) was kinetically analyzed under acidic conditions. Both 1 and 2 exhibited gradual spectral changes from zinc complexes to free-base forms with several isosbectic points in acetone/water (10: 1) at the proton concentration of 6.1 x 10(-3) M. Demetalation of zinc porphyrin 2 was slower than that of zinc chlorin 1 in the temperature range between 15 and 35 degrees C. This indicates that the porphyrin macrocycle provides tolerance to removal of the central metal from cyclic tetrapyrrole ligands compared with the chlorin macrocycle. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.019

文献信息

• Metallation of a cyclic chlorophyll hetero-dyad, and the optical properties of synthetic metallo-dyads
  作者：Hitoshi Tamiaki、Nobuo Kosaka、Yusuke Kinoshita

  DOI：10.1007/s11164-012-0644-4

  日期：2013.1

  A cyclic chlorophyll hetero-dyad 1-H2H2, prepared by double ester linking of two structurally different pyropheophorbide-a moieties through 3-CH2OCO-132′ and 172-COOCH2-3′, was metallated with zinc and copper to give mono and di-metallated complexes 1-MH2 or 1-H2M and 1-MM. The metallation proceeded stepwise and regioselectively, with predominant synthesis of one of the two mono-metallated complexes 1-MH2 as intermediate. The di-zinc complex produced, 1-ZnZn, was demetallated exclusively via the same mono-zinc complex 1-ZnH2 as was the major intermediate during metallation. Visible and/or circular dichroism spectra of 1-H2H2, 1-MH2, 1-H2M, and 1-MM (M = Ni, Cu, or Zn) were measured in organic solvents. Intramolecular interaction of chlorin chromophores is discussed and compared with that of the corresponding monomeric species.

  环状叶绿素杂二元体 1-H2H2，由两个结构不同的焦脱镁叶绿酸-a 部分通过 3-CH2OCO-132' 和 172-COOCH2-3' 双酯连接制备，用锌和铜金属化，得到单和二-金属化配合物1-MH2或1-H2M和1-MM。金属化以区域选择性的方式逐步进行，主要合成了两种单金属化配合物 1-MH2 之一作为中间体。所产生的二锌络合物 1-ZnZn 完全通过与金属化过程中主要中间体相同的单锌络合物 1-ZnH2 脱金属。在有机溶剂中测量 1-H2H2、1-M​​H2、1-H2M 和 1-MM（M = Ni、Cu 或 Zn）的可见光和/或圆二色光谱。讨论了二氢卟酚发色团的分子内相互作用，并与相应单体的分子内相互作用进行了比较。
• Isobacteriochlorophyll b analogs from photoreduction of metallochlorins
  作者：Kevin M. Smith、Daniel J. Simpson、Kevin M. Snow

  DOI：10.1021/ja00281a078

  日期：1986.10