(2R,3R)-2,3-Dimethyl-2,3-diphenyl-piperazine | 133604-00-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (2R,3R)-2,3-Dimethyl-2,3-diphenyl-piperazine
• 英文别名: (2R,3R)-2,3-dimethyl-2,3-diphenylpiperazine
• CAS: 133604-00-9
• 化学式: C₁₈H₂₂N₂
• 分子量: 266.386
• InChiKey: QRPUDMYTGKMENF-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  24.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N,N'-Bis-[1-phenyl-eth-(Z)-ylidene]-ethane-1,2-diamine 在 锰 、 吡啶盐酸盐 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 4.0h， 以30%的产率得到(2R,3R)-2,3-Dimethyl-2,3-diphenyl-piperazine
  参考文献：
  名称：

  通过锰介导的还原环化的非对映选择性合成哌嗪。

  摘要：

  描述了一种使用布朗斯台德酸和锰（0）的简单有效的合成反式芳基取代的哌嗪的方法。[反应：看文字]

  DOI：

  10.1021/ol034469l

文献信息

• Synthesis of Nitrogen-Containing Macrocycles with Reductive Intramolecular Coupling of Aromatic Diimines
  作者：Naoki Kise、Hideaki Oike、Eiichi Okazaki、Masami Yoshimoto、Tatsuya Shono

  DOI：10.1021/jo00118a013

  日期：1995.6

  Reductive intramolecular coupling of aromatic diimines is an effective method for the synthesis of a variety of nitrogen-containing macrocycles. 1,4-Diazacrown ethers 3 were effectively synthesized by intramolecular coupling of bis(imino ethers) 9 promoted by electroreduction (method A) or chemical reduction with zinc powder (method B) in the presence of methanesulfonic acid. In spite of the formation of macrocycles, the yields of 3 were relatively high. This can be explained by the formation of proton-bridged intermediates 14, in which intramolecular hydrogen bonds are formed between hydrogen and oxygen atoms of diiminium salts. Method B was more effective in the formation of 1,4-diaza-12-crown-4 derivatives 3 (n = 1) due to the template effect of Zn2+. Optically active macrocyclic bislactones 4 were synthesized stereoselectively by reductive intramolecular coupling of bis(imino esters) 20 with zinc powder (method B). The high stereoselectivity is explained by considering proton-bridged intermediate 23. The resultant compounds 4 were transformed to optically active 1,2-diarylethylenediamines 7. Various sizes of macrocyclic bislactams 5 were synthesized by reductive intramolecular coupling of bis(imino amides) 26 with zinc powder (method B). Reduction of 5 gave the corresponding macrocyclic polyamines 6.
• Electroorganic chemistry. 129. Electroreductive synthesis of chiral piperazines and enantioselective addition of diethylzinc to aldehydes in the presence of the chiral piperazines
  作者：Tatsuya Shono、Naoki Kise、Eiji Shirakawa、Hideshi Matsumoto、Eiichi Okazaki

  DOI：10.1021/jo00009a026

  日期：1991.4

  Electroreduction of diimines, prepared from 1,2-diamines and aromatic aldehydes, in acidic media gave intramolecularly coupled products, 2,3-diarylpiperazines, stereoselectively. Chiral tri- and tetrasubstituted piperazines were synthesized effectively from chiral 1,2-diamines by the same electroreductive method. Chiral piperazines, prepared from 1(R),2(R)-diaminocyclohexane were effective chiral ligands of catalysts for the enantioselective addition of diethylzinc to aldehydes.