6-(1,3-Dihydroxypropan-2-yl)-13-hexyl-6,13-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4(16),8,10-pentaene-5,7,12,14-tetrone | 171521-54-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 6-(1,3-Dihydroxypropan-2-yl)-13-hexyl-6,13-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4(16),8,10-pentaene-5,7,12,14-tetrone
• CAS: 171521-54-3
• 化学式: C₂₃H₂₄N₂O₆
• 分子量: 424.453
• InChiKey: KWZTVGCIVZFTIW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 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：

  pyropheophorbide-d methyl ester 、 6-(1,3-Dihydroxypropan-2-yl)-13-hexyl-6,13-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4(16),8,10-pentaene-5,7,12,14-tetrone 在 4-甲基苯磺酸吡啶 作用下， 以 苯 为溶剂， 反应 10.0h， 以29%的产率得到1,8:4,5-naphthalenetetracarboxamide-pyropheophorbide dyad
  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
• 作为产物：
  描述：

  正己胺 、 1,4,5,8-萘四甲酸酐 、 丝氨醇 以 N,N-二甲基甲酰胺 为溶剂， 以22%的产率得到6-(1,3-Dihydroxypropan-2-yl)-13-hexyl-6,13-diazatetracyclo[6.6.2.04,16.011,15]hexadeca-1(15),2,4(16),8,10-pentaene-5,7,12,14-tetrone
  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

• Coordination control of intramolecular electron transfer in boronate ester-bridged donor–acceptor molecules
  作者：Hideo Shiratori、Atsuhiro Osuka、Takeshi Ohno、Koichi Nozaki、Iwao Yamazaki、Yoshinobu Nishimura

  DOI：10.1039/a802473a

  日期：——

  Acid–base reaction at the bridge in a donor–acceptor molecule can influence intramolecular electron-transfer reactions; this has been demonstrated in boronate ester bridged zinc porphyrin–diimide dyads in which intramolecular electron transfer reaction has been completely suppressed by coordination of F– on the bridge boron.

  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。
• 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.