(3R,4R)-4-(benzoyloxy)pyrrolidin-3-yl benzoate | 259191-45-2

• 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: (3R,4R)-4-(benzoyloxy)pyrrolidin-3-yl benzoate
• 英文别名: (3R,4R)-3,4-dibenzoyloxypyrrolidine；[(3R,4R)-4-benzoyloxypyrrolidin-3-yl] benzoate
• CAS: 259191-45-2
• 化学式: C₁₈H₁₇NO₄
• 分子量: 311.337
• InChiKey: HAAQFGYDSSRHAM-HZPDHXFCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,4R)-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 、 甲苯 为溶剂， 反应 3.0h， 生成 (3R,4R)-3,4-dibenzoyloxy-1-pyrroline
  参考文献：
  名称：

  Preparation of14C-labelled 1,4-dideoxy-1,4-imino-D-arabinitol: cyanosilylation of cyclic imines using KCN in a one-pot synthesis

  摘要：

  A new method for C-C bond formation was developed based on ill situ cyanosilylation of cyclic Schiff bases using KCN, TMSCl, KI acid ZnI2. This method was used to prepare the potent alpha-glucosidase inhibitor 1,4-dideoxy-1,4-imino-D-arabinitol C-14 labelled at C-5.

  DOI：

  10.1002/(sici)1099-1344(199912)42:12<1145::aid-jlcr268>3.0.co;2-y
• 作为产物：
  描述：

  (3R,4R)-N-benzyl-3,4-dibenzoyloxypyrrolidine 在 palladium on activated charcoal 氢气 作用下， 以 溶剂黄146 为溶剂， 反应 24.0h， 以100%的产率得到(3R,4R)-4-(benzoyloxy)pyrrolidin-3-yl benzoate
  参考文献：
  名称：

  Preparation of14C-labelled 1,4-dideoxy-1,4-imino-D-arabinitol: cyanosilylation of cyclic imines using KCN in a one-pot synthesis

  摘要：

  A new method for C-C bond formation was developed based on ill situ cyanosilylation of cyclic Schiff bases using KCN, TMSCl, KI acid ZnI2. This method was used to prepare the potent alpha-glucosidase inhibitor 1,4-dideoxy-1,4-imino-D-arabinitol C-14 labelled at C-5.

  DOI：

  10.1002/(sici)1099-1344(199912)42:12<1145::aid-jlcr268>3.0.co;2-y

文献信息

• 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。
• Phosphonoxins: Rational design and discovery of a potent nucleotide anti-Giardia agent
  作者：Dae-Hwan Suk、Dominik Rejman、Christine C. Dykstra、Radek Pohl、Krzysztof W. Pankiewicz、Steven E. Patterson

  DOI：10.1016/j.bmcl.2007.02.063

  日期：2007.5

  Phosphonoxins, a new class of synthetic, rationally designed anti-microbial agents, are described. From this class a submicromolar inhibitor of Giardia trophozoite growth has been identified. (c) 2007 Elsevier Ltd. All rights reserved.
• Preparation of14C-labelled 1,4-dideoxy-1,4-imino-D-arabinitol: cyanosilylation of cyclic imines using KCN in a one-pot synthesis
  作者：Birgitte M. Folkersen、Inge Lundt、Christian Foged、Jacob S. Valsborg

  DOI：10.1002/(sici)1099-1344(199912)42:12<1145::aid-jlcr268>3.0.co;2-y

  日期：1999.12

  A new method for C-C bond formation was developed based on ill situ cyanosilylation of cyclic Schiff bases using KCN, TMSCl, KI acid ZnI2. This method was used to prepare the potent alpha-glucosidase inhibitor 1,4-dideoxy-1,4-imino-D-arabinitol C-14 labelled at C-5.