(3S,4S)-3,4-bis(benzyloxy)pyrrolidine | 515844-79-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3S,4S)-3,4-bis(benzyloxy)pyrrolidine
• 英文别名: (3S,4S)-3,4-dibenzyloxypyrrolidine；(3S,4S)-3,4-bis(phenylmethoxy)pyrrolidine
• CAS: 515844-79-8
• 化学式: C₁₈H₂₁NO₂
• 分子量: 283.37
• InChiKey: UNADCKDMLZFHOZ-ROUUACIJSA-N

物化性质

• 沸点：
  406.5±45.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3S,4S)-3,4-bis(benzyloxy)pyrrolidine 在 N-氯代丁二酰亚胺 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醚 为溶剂， 反应 4.5h， 生成 (3S,4S,8S,9S,13S,14S)-3,4,8,9,13,14-hexakis(phenylmethoxy)-1,6,11-triazatetracyclo[10.3.0.02,6.07,11]pentadecane
  参考文献：
  名称：

  A Diastereoselective Cyclic Imine Cycloaddition Strategy To Access Polyhydroxylated Indolizidine Skeleton: Concise Syntheses of (+)-/(−)-Lentiginosines and (−)-2-epi-Steviamine

  摘要：

  We describe in this paper the development of a novel diastereoselective cyclic imine cycloaddition strategy to access the polyhydroxylated indolizidine skeleton and its application in the concise syntheses of (+)-/(-)-lentiginosines and (-)-2-epi-steviamine.

  DOI：

  10.1021/jo3010777
• 作为产物：
  描述：

  (3S,4S)-3,4-Bis-benzyloxy-1-(toluene-4-sulfonyl)-pyrrolidine 在 sodium naphthalenide 作用下， 以48%的产率得到(3S,4S)-3,4-bis(benzyloxy)pyrrolidine
  参考文献：
  名称：

  使用新制备的酒石酸左旋酒酸酯的手性季铵盐进行相转移催化的不对称迈克尔反应

  摘要：

  使用新的PTCs证明了甘氨酸席夫碱的催化不对称迈克尔反应，并实现了中等至良好的ee（高达ee的77％）。

  DOI：

  10.1016/s0040-4039(02)02415-2

文献信息

• Improving cytotoxic properties of ferrocenes by incorporation of saturated N-heterocycles
  作者：Tomáš Hodík、Martin Lamač、Lucie Červenková Šťastná、Petra Cuřínová、Jindřich Karban、Hana Skoupilová、Roman Hrstka、Ivana Císařová、Róbert Gyepes、Jiří Pinkas

  DOI：10.1016/j.jorganchem.2017.06.005

  日期：2017.10

  selected ferrocene derivatives were determined by X-ray diffraction analysis. The ferrocene derivatives and the ruthenium complexes were tested in vitro for their cytotoxic properties against three cell lines derived from ovarian cancer (A2780, A2780cis, and SK-OV-3) and against non-tumour embryonic cell line HEK293 (human kidney cells). The most active ferrocene derivatives displayed cytotoxicity in submicromolar

  通式的二茂铁衍生物的家族的[Fe（η 5 -C 5 H ^ 4 CH 2（p -C 6 H ^ 4）CH 2（N-HET））2 ]轴承饱和六元和五元N-杂环（N-het）已准备好。所选择的配合物与酸（HCl，乙酸）的反应提供相应的盐酸盐或导致官能化的侧链N-杂环的脱保护。的[茹（η反应6 - p氯-cymene）2 } 2与相应的环戊二烯衍生物，得到的阳离子钌络合物的[Ru（η] 6- p -cymene）（η 5 -C 5 H ^ 4 CH 2（p -C 6 H ^ 4）CH 2（N-HET））]氯而ruthenocenes的[Ru（η 5 -C 5 H ^ 4 CH 2（p - C 6 H 4）CH 2（N-het））2形成副产物。通过元素分析，熔点，NMR和ESI-MS对制备的配合物（20个实施例）进行表征，并通过X射线衍射分析确定所选择的二茂铁衍生物的分子结构。二茂铁衍生物和钌配
• Phase-transfer-catalyzed asymmetric Michael reaction using newly-prepared chiral quaternary ammonium salts derived from l-tartrate
  作者：Shigeru Arai、Riichiro Tsuji、Atsushi Nishida

  DOI：10.1016/s0040-4039(02)02415-2

  日期：2002.12

  The catalytic asymmetric Michael reaction of a glycine Schiff base was demonstrated using new PTCs and moderate to good ee's were achieved (up to 77% ee).

  使用新的PTCs证明了甘氨酸席夫碱的催化不对称迈克尔反应，并实现了中等至良好的ee（高达ee的77％）。
• Design of Branched and Chiral Solvatochromic Probes:  Toward Quantifying Polarity Gradients in Dendritic Macromolecules
  作者：Petar Milosevic、Stefan Hecht

  DOI：10.1021/ol0519902

  日期：2005.10.1

  [GRAPHICS]A pair of chiral, branched monomer building blocks, consisting of a solvatochromic probe and a spectroscopically inactive volume dummy, has been developed. The probe can selectively be excited, and its fluorescence characteristics provide information about local polarity. Incorporation of these monomers into high-generation polyester clendrimers should enable a detailed investigation of the polarity/density profile in dendritic architectures and ultimately allow for the realization of energy gradients from one chromophore building block only.
• A Diastereoselective Cyclic Imine Cycloaddition Strategy To Access Polyhydroxylated Indolizidine Skeleton: Concise Syntheses of (+)-/(−)-Lentiginosines and (−)-2-<i>epi</i>-Steviamine
  作者：Jia Shao、Jin-Song Yang

  DOI：10.1021/jo3010777

  日期：2012.9.21

  We describe in this paper the development of a novel diastereoselective cyclic imine cycloaddition strategy to access the polyhydroxylated indolizidine skeleton and its application in the concise syntheses of (+)-/(-)-lentiginosines and (-)-2-epi-steviamine.