d,l-1,2-dipiperidino-1,2-diphenylethane | 94533-64-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: d,l-1,2-dipiperidino-1,2-diphenylethane
• 英文别名: (+/-)-N,N,N',N'-bis(pentamethylen)-1,2-diphenylaethylendiamin；dl-1,2-diphenyl-1,2-di(piperidin-1-yl)ethane；1-[(1S,2S)-1,2-diphenyl-2-piperidin-1-ylethyl]piperidine
• CAS: 94533-64-9
• 化学式: C₂₄H₃₂N₂
• 分子量: 348.531
• InChiKey: MTYFDEYZRYWPAI-ZEQRLZLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  d,l-1,2-dipiperidino-1,2-diphenylethane 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 0.17h， 生成
  参考文献：
  名称：

  Aminierende，还原性Kupplung芳香族醛mit三（二烷基氨基）甲基钒（IV）zu N，N，N '，N'-四烷基-1,2-二芳基二亚乙基二胺

  摘要：

  三（二烷基氨基）甲基钒（IV）诱导的芳香醛与N，N，N '，N'-四烷基-1,2-二芳基乙二胺的胺还原还原偶联

  DOI：

  10.1002/hlca.19840670612
• 作为产物：
  描述：

  1-[Ethoxy(phenyl)methyl]piperidine 在 碘化钛(IV) 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 meso-N,N,N',N'-bis(pentamethylen)-1,2-diphenylaethylendiamin 、 d,l-1,2-dipiperidino-1,2-diphenylethane
  参考文献：
  名称：

  一种通过低价碘化钛物质介导的氨基缩醛还原偶联制备邻位叔二胺的有效方法

  摘要：

  氨基缩醛很容易通过芳香醛、仲胺和醇的缩合制备，通过使用低价碘化钛物种还原偶联，在温和的反应条件下以良好到高产率得到相应的偶联产物，即邻位叔二胺。

  DOI：

  10.1246/cl.2001.1334

文献信息

• An Efficient Method for the Preparation of Vicinal Tertiary Diamines by Reductive Coupling of Aminoacetals Mediated by Low Valent Titanium Iodide Species
  作者：Naritoshi Yoshimura、Teruaki Mukaiyama

  DOI：10.1246/cl.2001.1334

  日期：2001.12

  Aminoacetals, easily prepared by condensation of aromatic aldehydes, secondary amines and alcohols, are reductively coupled by using low valent titanium iodide species to afford the corresponding coupling products, vicinal tertiary diamines, in good to high yields under mild reaction conditions.

  氨基缩醛很容易通过芳香醛、仲胺和醇的缩合制备，通过使用低价碘化钛物种还原偶联，在温和的反应条件下以良好到高产率得到相应的偶联产物，即邻位叔二胺。
• Photochemistry of Intramolecular Charge Transfer Excited States in Donor-Acceptor-Substituted Diamines
  作者：Yingsheng Wang、Kirk S. Schanze

  DOI：10.1021/j100018a019

  日期：1995.5

  The photochemistry and photophysics of 1,2-diamines C(5)H(10)NCHPhCHPhNHC(6)H(4)R (1, R = CN, and 2, R = 4-pyridyl) have been examined. These compounds display a strong absorption band in the near-UV which is due to intramolecular charge transfer from the secondary amine group to the 4-cyanophenyl or (4-pyridyl)phenyl acceptor unit. Photoexcitation into this absorption band leads to moderately intense fluorescence from the (1)LE state of the charge transfer chromophore and to homolytic bond fragmentation across the 1,2 C-C bond with moderate quantum efficiency. Detailed photochemical and photophysical studies reveal that the bond fragmentation reaction ensues from a second intramolecular charge transfer excited state (denoted (CT)-C-1) which is based on electron transfer from the tertiary piperidine nitrogen to the 4-cyanophenyl or (4-pyridyl)phenyl unit. Photochemical product analysis reveals that erythro --> three (or three --> erythro) isomerization occurs under both argon-degassed and air-saturated conditions. This observation indicates that recombination of the radicals formed by bond fragmentation occurs, both within the geminate pair and between free radicals that have escaped the solvent cage. Analysis of fluorescence, transient absorption, and steady-state photochemical kinetics data indicates that (1) internal conversion from the (1)LE state to the (CT)-C-1 state by intramolecular electron transfer occurs with k greater than or equal to 10(9) s(-1) in all of the diamines; (2) bond fragmentation within the (CT)-C-1 state occurs with k greater than or equal to 10(8) s(-1) in each of the diamines: (3) bond fragmentation may be faster in erythro-1 than in threo-1.
• Reductive coupling of aromatic N,N-acetals using zinc and chlorotrimethylsilane
  作者：Bunpei Hatano、Tomoharu Tachikawa、Tetsunori Mori、Keita Nagahashi、Tatsuro Kijima

  DOI：10.1016/j.tetlet.2011.04.104

  日期：2011.7

  The reductive coupling of aromatic N,N-acetals and N,O-acetal activated by chlorotrimethylsilane proceeded smoothly in the presence of zinc to give the corresponding diamines in good yields.

  在锌的存在下，由氯三甲基硅烷活化的芳族N，N-乙缩醛和N，O-乙缩醛的还原偶联反应顺利进行，从而以良好的收率得到了相应的二胺。
• Aminierende, reduktive Kupplung aromatischer Aldehyde mit Tris(dialkylamino)methylvanandium (IV) zuN,N,N?,N?-Tetraaalkyl-1,2-diaryl�thylendiaminen
  作者：Ren� Imwinkelried、Dieter Seebach

  DOI：10.1002/hlca.19840670612

  日期：1984.9.26

  Aminative Reductive Coupling of Aromatic Aldehydes to N,N,N′,N′-Tetraalkyl-1,2-diarylethylenediamines, Induced by Tris(dialkylamino)methylvanadium (IV)

  三（二烷基氨基）甲基钒（IV）诱导的芳香醛与N，N，N '，N'-四烷基-1,2-二芳基乙二胺的胺还原还原偶联