1-(4-formylphenyl)-4-phthalimidopiperidine | 321733-40-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-(4-formylphenyl)-4-phthalimidopiperidine
• 英文别名: 4-[4-(1,3-Dioxoisoindol-2-yl)piperidin-1-yl]benzaldehyde
• CAS: 321733-40-8
• 化学式: C₂₀H₁₈N₂O₃
• 分子量: 334.375
• InChiKey: YDURJVGBNBLOOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  57.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-双(叔丁基)苯甲醛 、 bis(3-hexyl-4-methyl-2-pyrrolyl)methane 、 1-(4-formylphenyl)-4-phthalimidopiperidine 在 三氯乙酸 、 四氯苯醌 作用下， 以 乙腈 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  Coordination Control of Intramolecular Electron Transfer in Boronate-Bridged Zinc PorphyrinDiimide Molecules

  摘要：

  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.

  DOI：

  10.1021/jo001281w
• 作为产物：
  描述：

  4-氨基-1-苄基哌啶 在 tris(dibenzylideneacetone)dipalladium (0) N,N-二甲基乙酰胺 、 硫酸 、 potassium tert-butylate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 三氟乙酸 作用下， 以 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 21.0h， 生成 1-(4-formylphenyl)-4-phthalimidopiperidine
  参考文献：
  名称：

  Coordination Control of Intramolecular Electron Transfer in Boronate-Bridged Zinc PorphyrinDiimide Molecules

  摘要：

  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.

  DOI：

  10.1021/jo001281w

文献信息

• 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.