(+)-(3S,4S)-3,4-Diphenylpyrrolidine | 144901-29-1

• 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: (+)-(3S,4S)-3,4-Diphenylpyrrolidine
• 英文别名: trans-(3S,4S)-diphenylpyrrolidine；(3S,4S)-3,4-diphenylpyrrolidine
• CAS: 144901-29-1
• 化学式: C₁₆H₁₇N
• 分子量: 223.318
• InChiKey: KCUJZQHVIDHUQU-HZPDHXFCSA-N

物化性质

• 沸点：
  347.9±31.0 °C(Predicted)
• 密度：
  1.047±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (+)-(3S,4S)-3,4-Diphenylpyrrolidine 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.34h， 生成 (3S,3'S,4S,4'S)-3,3',4,4'-tetraphenyl-1,1'-ethylenedipyrrolidine
  参考文献：
  名称：

  Design and synthesis of novel chiral pyrrolidine-based diamines with C2-symmetry

  摘要：

  Novel chiral pyrrolidine-based diamines with C2-symmetry 2, 3 and their related compounds 4 - 8 were designed and synthesized in optically pure forms. Both (+)- and (-)-2 were prepared from optical active ditosylate 9. 3 was prepared from 3,5-dimethylbenzaldehyde through optical resolution and its absolute stereochemistry was correlated with 2,3-dimethylsuccinate 27. 4 was prepared from (-)-diol 28. 5 - 8 were prepared from 9 and 11.

  DOI：

  10.1016/s0040-4020(01)80176-9
• 作为产物：
  描述：

  ethyl (3S,4S)-3,4-diphenylpyrrolidine-1-carboxylate 在 N,N-diethylaniline-BI₃ 作用下， 以 苯 为溶剂， 反应 8.0h， 以89%的产率得到(+)-(3S,4S)-3,4-Diphenylpyrrolidine
  参考文献：
  名称：

  Convenient Method for N-Debenzylation of Tertiary Amines

  摘要：

  N-Benzyl tertiary amines on reaction with ethyl chloroformate give the corresponding debenzylated N-carbamates which on treatment with I3B:N(C2H5)(2)Ph complex yield the secondary amines.

  DOI：

  10.1080/00397919408011190

文献信息

• The use of the β-amino-alcohol-n-oxide derivatives in the synthesis of 2,3 or 4-alkyl substituted nh pyrrolidines
  作者：Georges Roussi、Jidong Zhang

  DOI：10.1016/s0040-4020(01)87128-3

  日期：1991.1

  Nonstabilized azomethine ylides generated from the various β-amino alcohols N-oxides 13, 17, 23 and 24 undergo [3+2] cycloaddition reactions with unactivated alkenes to afford the corresponding pyrrolidines 14a-g, 18a-g, 25 and 27 in moderate to good yields. These compounds are precursors of NH pyrrolidines substituted in position 2, 3 or 4.

  来自各个β氨基醇生成Nonstabilized甲亚胺叶立德N-氧化物13，17，23和24经历[3 + 2]与未活化的烯烃，得到相应的吡咯烷环加成反应14A-G ，18A-G ，25和27在适度高产。这些化合物是在2、3或4位取代的NH吡咯烷的前体。
• (S)-2H-2-oxo-5,5-dimethyl-4(R)-phenyl-1,3,2-dioxaphosphorinane, a new reagent for the enantiomeric excess determination of unprotected amino acids using 31P NMR
  作者：Ron Hulst、Robert W.J. Zijlstra、N.Koen de Vries、Ben L. Feringa

  DOI：10.1016/0957-4166(94)80081-2

  日期：1994.9

  Diastereomeric amide derivatives of title phosphorinane 2 and unprotected amino acids are easily prepared in aqueous solutions, showing well separated signals in the 31P NMR spectra allowing accurate e.e. determination.

  在水溶液中可以轻松制备标题膦烷2和非保护氨基酸的非对映异构酰胺衍生物，在31 P NMR光谱中显示出分离良好的信号，从而可以准确测定ee。
• A new 31P NMR method for the enantiomeric excess determination of alcohols, amines and amino acid esters
  作者：Ron Hulst、Robert W.J. Zijlstra、Ben L. Feringa、N.Koen de Vries、Wolter ten Hoeve、Hans Wynberg

  DOI：10.1016/s0040-4039(00)91790-8

  日期：1993.2

  Diastereoisomeric ester and amide derivatives of phosphoric acid chloride 2 show well separated signals in the 31P NMR spectra allowing accurate e.e. determination of chiral alcohols, esters of amino acids and amines.

  磷酸氯化物2的非对映异构体酯和酰胺衍生物在31 P NMR光谱中显示出良好分离的信号，从而可以准确EE测定手性醇，氨基酸和胺的酯。
• Method of Producing Macrocyclic Ketone, and Intermediate Thereof
  申请人：Matsuda Hiroyuki

  公开号：US20070287870A1

  公开（公告）日：2007-12-13

  A process for producing muscone by methyl addition to the 1,4-conjugation of 2-cyclopentadecenone. By the process, muscone is produced in high yield not under reaction condition including an extremely low temperature and a low concentration but under practical condition. The process comprises subjecting 2-cyclopentadecenone to a 1,4-conjugation addition reaction with an organometallic methylation reagent in the presence of a copper or nickel catalyst and an enol anion scavenger to obtain a 3-methyl-1-cyclopentadecene derivative represented by General Formula (II) and then solvolyzing the enol moiety of the 3-methyl-1-cyclopentadecene derivative to obtain muscone.

  通过对2-环戊十五烯酮的1,4-共轭加成进行甲基化反应制备肉麝香的方法。该过程在实用条件下而非包括极低温度和低浓度的反应条件下高产肉麝香。该过程包括将2-环戊十五烯酮与有机金属甲基试剂在铜或镍催化剂和烯醇阴离子清除剂的存在下进行1,4-共轭加成反应，以获得由通式（II）表示的3-甲基-1-环戊十五烯衍生物，然后溶解3-甲基-1-环戊十五烯衍生物的烯醇基团以获得肉麝香。
• Convenient method for the synthesis of chiral α,α-diphenyl-2-pyrrolidinemethanol
  作者：J.V. Bhaskar Kanth、Mariappan Periasamy

  DOI：10.1016/s0040-4020(01)81877-9

  日期：1993.6