3-formylmethyl-3-devinylpyropheophorbide-a methyl ester | 66229-99-0

• 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-formylmethyl-3-devinylpyropheophorbide-a methyl ester
• 英文别名: methyl 2-formylmethyl-2-devinylpyropheophorbide-a；methyl 3²-oxomesopyropheophorbide a；3²-oxo-mesopyropheophorbide-a；3-[14-ethyl-4,8,13,18-tetramethyl-20-oxo-9-(2-oxo-ethyl)-23H,25H-phorbin-3-yl]-propionic acid methyl ester
• CAS: 66229-99-0
• 化学式: C₃₄H₃₆N₄O₄
• 分子量: 564.684
• InChiKey: ZHRDABXADSQOEQ-KFCORYJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.59
• 重原子数：
  42.0
• 可旋转键数：
  6.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  117.8
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  3-formylmethyl-3-devinylpyropheophorbide-a methyl ester 在 硫酸 、 铬酸 作用下， 以 水 为溶剂， 生成
  参考文献：
  名称：

  New Water-soluble pyropheophorbide a derivatives as possible agents for photodynamic therapy of cancer

  摘要：

  Five new water-soluble pyroPPBa derivatives, whose vinyl groups at position 2 were converted into hydrophilic groups, were synthesized, and their in vivo tumor retention was measured by the N2-pulsed laser spectrofluorometry method. The results suggested that these derivatives were advantageous to reduce hyperphotosensitivity in skin, a major side effect of photodynamic therapy.

  DOI：

  10.1016/s0040-4039(00)93440-3
• 作为产物：
  描述：

  methyl 2-(2,2-dimethoxyethyl)-2-devinylpyropheophorbide a 在 甲酸 作用下， 反应 4.0h， 生成 3-formylmethyl-3-devinylpyropheophorbide-a methyl ester
  参考文献：
  名称：

  叶绿素a合成叶绿素a-具有线性六碳链的骨架同系物

  摘要：

  二氢卟酚轴承6C-直链的从甲基被完成的合成pheophorbide-一个。一系列化学修饰被用于在二氢卟酚的外围上构建活性官能团，例如溴原子或醛基。这些官能化的二氢卟酚还通过通常的化学反应与含有直碳链的试剂反应，生成目标化合物。所有新二氢卟酚的结构均通过元素分析，IR，UV-Vis和1 H NMR光谱进行了表征。

  DOI：

  10.1007/bf03246552

文献信息

• Synthesis and epoxide-opening reaction of a 3-oxiranyl-chlorophyll derivative
  作者：Shinnosuke Machida、Yasuaki Isoda、Michio Kunieda、Hitoshi Tamiaki

  DOI：10.1016/j.tetlet.2012.09.029

  日期：2012.11

  synthesized from methyl pyropheophorbide-d bearing the 3-formyl group under Corey–Chaykovsky reaction conditions in a good yield. The ring-opening reaction of the protonated epoxide-moiety with various nucleophiles gave the 31-adducts with high regioselectivity, while the treatment of BF3·Et2O afforded an isomeric 3-(formylmethyl) chlorin as the sole isolable product. The above ring-opening hardly affected

  在C3位具有环氧乙烷基甲叶绿素衍生物从甲基pyropheophorbide-合成d轴承科里-Chaykovsky反应条件下的3-甲酰基以良好的产率。质子化的环氧化物部分与各种亲核试剂的开环反应产生具有高区域选择性的3 1-加合物，而BF 3 ·Et 2 O的处理提供了异构的3-（甲酰基甲基）二氢卟酚作为唯一的可分离产物。上述开环几乎不影响它们的可见吸收光谱，在二氯甲烷中分别在大约660和410 nm处产生相似的Qy和Soret带。
• Synthesis of carboxylated chlorophyll derivatives and their activities in dye-sensitized solar cells
  作者：Hitoshi Tamiaki、Norihisa Hagio、Shinsaku Tsuzuki、Yuxiao Cui、Taisuke Zouta、Xiao-Feng Wang、Yusuke Kinoshita

  DOI：10.1016/j.tet.2018.06.017

  日期：2018.7

  the 3-position were prepared by chemical modification of methyl pyropheophorbide-d bearing the 3-formyl group via a Wittig, Barbier-type, or Knoevenagel reaction. The synthetic carboxylated chlorophyll pigments were employed as dye sensitizers for solar cells and their performances were compared in a conventional device based on a mesoporous titanium dioxide electrode and a liquid electrolyte. The solar

  叶绿素一个衍生物在3位具有羧基中的取代基是由甲基pyropheophorbide-的化学改性制备d轴承3-甲酰基通过维悌希，巴比尔型，或Knoevenagel反应。将合成的羧化叶绿素颜料用作太阳能电池的染料敏化剂，并在基于介孔二氧化钛电极和液体电解质的常规装置中比较了它们的性能。通过增加二氢卟酚π系统和羧基之间的低聚亚甲基部分的长度来抑制太阳能转换效率，而相应的π连接的亚乙基间隔基提高了效率。
• Synthesis of heterocycle-substituted pyropheophorbide derivatives
  作者：Jin-Jun Wang、Young Key Shim、Gui-Ji Jiang、Kimiaki Imafuku

  DOI：10.1002/jhet.5570400617

  日期：2003.11

  Methyl pyropheophorbide-a (MPPa) (1) was converted to two aldehydes, methyl 2-formylmethyl-2-devinylpyropheophorbide-a (2) and methyl 2-formyl-2-devinylpyropheophorbide-a (3). The former 2 reacted with active methylene compounds having a cyano function in the presence of sulfur to afford thiophene-substituted chlorins 5a-c and reacted with arylhydrazines to yield indole-substituted chlorins 6a-d. From

  甲基pyropheophorbide-一个（MPPA）（1）转化为两种醛，2-甲酰基甲基-2- devinylpyropheophorbide-一个（2）和甲基2-甲酰基-2- devinylpyropheophorbide-一个（3）。前者2在硫的存在下与具有氰基官能的活性亚甲基化合物反应，得到噻吩取代的二氢卟酚5a-c，并与芳基肼反应，得到吲哚取代的二氢卟酚6a-d。从后者3，一个α二酮二氢7获得通过Wittig反应和氧化。化合物7与反应ø苯二胺，得到2-喹喔啉基取代的pyropheophorbide-一个 8. MPPA（的反应1）邻氨基苯甲酰胺用，得到螺取代的化合物9。