1-[4-(5,5-dimethyl-1,3-dioxan-2-yl)phenyl]piperidine | 321733-38-4

• 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-(5,5-dimethyl-1,3-dioxan-2-yl)phenyl]piperidine
• CAS: 321733-38-4
• 化学式: C₁₇H₂₅NO₂
• 分子量: 275.391
• InChiKey: QHLIJBUCKFMJHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[4-(5,5-dimethyl-1,3-dioxan-2-yl)phenyl]piperidine 在 硫酸 、 三氟乙酸 作用下， 反应 2.0h， 以73%的产率得到4-哌啶-1-基-苯甲醛
  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：

  哌啶 、 1,3-二噁烷,2-(4-溴苯基)-5,5-二甲基- 在 tris(dibenzylideneacetone)dipalladium (0) potassium tert-butylate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以49%的产率得到1-[4-(5,5-dimethyl-1,3-dioxan-2-yl)phenyl]piperidine
  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.