2-Hexyl-6-(2-hydroxy-1-hydroxymethyl-ethyl)-pyrrolo[3,4-f]isoindole-1,3,5,7-tetraone | 155526-45-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-Hexyl-6-(2-hydroxy-1-hydroxymethyl-ethyl)-pyrrolo[3,4-f]isoindole-1,3,5,7-tetraone
• 英文别名: 2-(1,3-Dihydroxypropan-2-yl)-6-hexylpyrrolo[3,4-f]isoindole-1,3,5,7-tetrone
• CAS: 155526-45-7
• 化学式: C₁₉H₂₂N₂O₆
• 分子量: 374.393
• InChiKey: ZBBGEOQEWYVZOO-UHFFFAOYSA-N

物化性质

• 沸点：
  604.8±55.0 °C(predicted)
• 密度：
  1.405±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  115
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-Hexyl-6-(2-hydroxy-1-hydroxymethyl-ethyl)-pyrrolo[3,4-f]isoindole-1,3,5,7-tetraone 、 以 甲苯 为溶剂， 以84%的产率得到
  参考文献：
  名称：

  Coordination control of intramolecular electron transfer in boronate ester-bridged donor–acceptor molecules

  摘要：

  供体-受体分子桥上的酸碱反应会影响分子内电子转移反应；这一点已在硼酸酯桥联锌卟啉-二亚胺二聚体中得到证实，其中分子内电子转移反应被桥上的氟-硼配位所完全抑制。

  DOI：

  10.1039/a802473a
• 作为产物：
  描述：

  正己胺 、 丝氨醇 、 pyromellitic imide anhydride 以 N,N-二甲基甲酰胺 为溶剂， 以35%的产率得到2-Hexyl-6-(2-hydroxy-1-hydroxymethyl-ethyl)-pyrrolo[3,4-f]isoindole-1,3,5,7-tetraone
  参考文献：
  名称：

  Synthesis of 1,3-Dioxane-Bridged Pyropheophorbide-Diimide and Pyropheophorbide Dimer and Their Intramolecular Electron and Energy Transfer

  摘要：

  通过简单的酸催化反应，分别以二氟代二醇和五元醇为原料合成了1,3-二氧桥联的火葱藻叶绿素–二酰亚胺双体以及火葱藻叶绿素二聚体。1,3-二氧桥联的细菌火葱藻叶绿素–二酰亚胺也类似地由细菌火葱藻叶绿素a制备而成。这些模型中的分子内电子转移和能量转移反应已通过皮秒荧光测量进行研究。

  DOI：

  10.1246/bcsj.68.2909

文献信息

• 1,3-Dioxane-Bridged Pyromellitimide-Pyropheophorbide and Pyropheophorbide Dimer
  作者：Atsuhiro Osuka、Shinji Marumo、Norifumi Konishi、Kazuhiro Maruyama、Iwao Yamazaki、Tomoko Yamazaki、Yoshihiro Shirakawa、Yoshinobu Nishimura

  DOI：10.1246/cl.1993.2141

  日期：1993.12

  1,3-Dioxane-bridged pyromellitimide-pyropheophorbide dyads were synthesized by simple acid-catalyzed reaction of methyl pyropheophorbide-d and a pyromellitimide-substituted diol. A bis-1,3-dioxane-bridged pyropheophorbide dimer was similarly prepared by the reaction of methyl pyropheophorbide-d and pentaerythritol. Intramolecular electron-transfer and energy-transfer reactions in these models have been studied by picosecond fluorescence measurements.

  1,3-二氧六环桥连的吡咯二甲酰亚胺-吡咯叶绿素二聚体通过简单酸催化反应，由甲基吡咯叶绿素-d和吡咯二甲酰亚胺取代的二醇合成得到。同样地，通过甲基吡罗叶绿素-d与季戊四醇的反应制备了双-1,3-二氧六环桥连的吡咯叶绿素二聚体。通过皮秒荧光测量研究了这些模型分子中的分子内电子转移和能量转移反应。
• Coordination Control of Intramolecular Electron Transfer in Boronate-Bridged Zinc PorphyrinDiimide Molecules
  作者：Hideo Shiratori、Takeshi Ohno、Koichi Nozaki、Iwao Yamazaki、Yoshinobu Nishimura、Atsuhiro Osuka

  DOI：10.1021/jo001281w

  日期：2000.12.1

  Three sets of dyads, in which a zinc-porphyrin (ZP) electron donor is connected to an aromatic diimide electron acceptor,either pyromellitimide (PI) or naphthalene-1,8:4,5-tetracarboxylic acid diimide (NI), via a boronate-ester bridge, a piperidine bridge, and a 1,3-dioxolane bridge, respectively, were prepared for the purpose of control of intramolecular electron transfer (ET) by acid-base reactions at the connecting bridge. Boronate-ester bridge is a Lewis acidic site and confers a chance to regulate intramolecular ET reaction upon base coordination. This has been demonstrated by suppression of photoinduced ET from ZP to PI or NI in highly electron-pair donating solvents or upon addition of a fluoride anion. To extend this strategy to control of ET-path selectivity, we prepared triad 18, which consists of a ZP donor bearing NI and PI accepters at similar distances through a boronate-ester bridge and an acetal bridge, respectively. Photoexcitation of 18 in a free form led to intramolecular ET from (1)ZP* preferentially to. NI, but the ET path was completely sw itched toward PI in F--coordinated form without a serious drop in the rate, constituting a novel ET-switching molecular system.