(3S,4S)-4-(benzoyloxy)pyrrolidin-3-yl benzoate | 138228-46-3

• 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)-4-(benzoyloxy)pyrrolidin-3-yl benzoate
• 英文别名: (S,S)-3,4-bis(phenylacetoxy)pyrrolidine；(3S,4S)-3,4-dibenzoyloxypyrrolidine；[(3S,4S)-4-benzoyloxypyrrolidin-3-yl] benzoate
• CAS: 138228-46-3
• 化学式: C₁₈H₁₇NO₄
• 分子量: 311.337
• InChiKey: HAAQFGYDSSRHAM-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.04
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  64.63
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (3S,4S)-4-(benzoyloxy)pyrrolidin-3-yl benzoate 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 、 苯 为溶剂， 反应 2.0h， 生成 (3S,4S)-3,4-dibenzoyloxypyrroline
  参考文献：
  名称：

  Synthesis of (3S,4S)-3,4-Dihydroxyprolines from L-Tartaric Acid.

  摘要：

  通过环状席夫碱的氰基甲硅烷基化，由 L-酒石酸合成了天然 (2S, 3S, 4S)-3, 4-二羟基脯氨酸 (1) 和新的 (2R, 3S, 4S)-异构体 (7)。

  DOI：

  10.1248/cpb.39.2219
• 作为产物：
  描述：

  (3S,4S)-3,4-dibenzoyloxy-1-benzylpyrrolidine 在 palladium dihydroxide 氢氧化钾 、 氢气 、 溶剂黄146 作用下， 生成 (3S,4S)-4-(benzoyloxy)pyrrolidin-3-yl benzoate
  参考文献：
  名称：

  Synthesis of (3S,4S)-3,4-Dihydroxyprolines from L-Tartaric Acid.

  摘要：

  通过环状席夫碱的氰基甲硅烷基化，由 L-酒石酸合成了天然 (2S, 3S, 4S)-3, 4-二羟基脯氨酸 (1) 和新的 (2R, 3S, 4S)-异构体 (7)。

  DOI：

  10.1248/cpb.39.2219

文献信息

• Enantioselective Vicinal Bis-Acylation of Olefins
  作者：Léon Ghosez、Florence Mahuteau-Betzer、Christophe Genicot、Adelina Vallribera、Jean-François Cordier

  DOI：10.1002/1521-3765(20020802)8:15<3411::aid-chem3411>3.0.co;2-a

  日期：2002.8.2

  A two-step sequence for the asymmetric vicinal acylation of olefins by a [2+2+1] strategy is reported. The key reaction is a [2+2] cycloaddition of an olefin to a chiral keteniminium salt derived from N-tosylsarcosinamide. This is followed by a regioselective Baeyer-Villiger oxidation of the resulting cyclobutanone to yield a lactol derivative that is equivalent to the product of addition of a carboxyl

  报道了通过[2 + 2 + 1]策略进行烯烃不对称邻位酰化的两步序列。关键反应是烯烃与衍生自N-甲苯磺酰基肌氨酸酰胺的手性酮亚胺盐的[2 + 2]环加成反应。随后是所得环丁酮的区域选择性的Baeyer-Villiger氧化，以生成丙三醇衍生物，其等同于将羧基和羰基加成至烯烃。衍生自脯氨醇甲基醚和2,5-二甲基吡咯烷的N-甲苯磺酰基肌氨酸酰胺具有最佳的收率和非对映选择性。五元和六元环烯烃仅产生预期的顺式产物。在具有七元和八元环和顺式1，2-二取代的无环烯烃的情况下，观察到顺式部分或完全差向异构化为反式加合物。除末端烯烃外，表面选择性总体上良好。氧化步骤以高收率进行，得到结晶化合物，其通常可以通过简单的重结晶以对映纯形式获得。
• Diversity-oriented syntheses of 7-substituted lentiginosines
  作者：Franca M. Cordero、Paola Bonanno、Matteo Chioccioli、Paola Gratteri、Inmaculada Robina、Antonio J. Moreno Vargas、Alberto Brandi

  DOI：10.1016/j.tet.2011.10.008

  日期：2011.12

  synthesis of derivatives of the potent glycosidase inhibitor lentiginosine can be achieved in an efficient and versatile way by two modular approaches on key intermediates. After assembling the indolizidine ring system through 1,3-dipolar cycloaddition of a dihydroxylated pyrroline N-oxide with 4-butenol followed by elaboration of the isoxazolidine moiety, the 7-amino and 7-azido derivatives synthesized

  通过在关键中间体上采用两种模块化方法，可以有效且通用的方式实现有效的糖苷酶抑制剂lentiginosine衍生物的多样性导向合成。通过二羟基化的吡咯啉N-氧化物与4-丁烯醇的1,3-偶极环加成，然后精制异恶唑烷部分，组装吲哚并咪唑环系统后，可以通过偶联使合成的7-氨基和7-叠氮基衍生物与官能化链偶联分别在铜催化的惠斯根环加成中与氨基酸或炔烃结合。
• Hydrogen-Bonding Complexes of 5-Azauracil and Uracil Derivatives in Organic Medium
  作者：Alba Diez-Martinez、Eun-Kyong Kim、Ramanarayanan Krishnamurthy

  DOI：10.1021/acs.joc.5b00911

  日期：2015.7.17

  Uracil derivatives form strong complexes with complementary 2,4-diaminotriazine and adenine compounds, whereas derivatives of 5-azauracil (2,4-dioxotriazine) are known to form weak complexes in aqueous medium. However, herein we report that in organic medium (CDCl3), the 5-azauracil moiety forms hydrogen-bond-mediated complexes with complementary 2,4-diaminotriazine and adenine compounds, with strengths comparable to those formed by uracil compounds. Such dichotomous base-pairing behavior of the 5-azauracil moiety, in organic versus aqueous media, is found to be consistent with the ionization of the 5-azauracil moiety in aqueous medium leading to competitive interference from water molecules (via solvation), which is absent (lack of such ionization and solvent interference) in organic medium. This discriminating role of solvent (e.g., water) could have been an important factor in the selection of molecules, based on their physicochemical properties, and subsequently in the emergence of potential primordial informational oligomers that would have played a role in the origins of life.
• Synthesis of the New 7<i>S</i>-Aminolentiginosine and Derivatives
  作者：Franca M. Cordero、Paola Bonanno、Sven Neudeck、Carolina Vurchio、Alberto Brandi

  DOI：10.1002/adsc.200800806

  日期：2009.5

  Abstractmagnified imageThe new 7S‐aminolentiginosine has been synthesized by a diastereoselective 1,3‐dipolar cycloaddition strategy starting from 3,4‐dihydroxylated pyrroline N‐oxides derived from L‐tartaric acid in thirteen steps. The intermediate 7S‐azidolentiginosine undergoes efficiently copper(I)‐catalysed Huisgen cycloadditions to alkynes.