(1S,2S,8aS)-1,2-bis(benzyloxy)-2,3,8,8a-tetrahydroindolizin-7(1H)-one | 1400236-11-4

• 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: (1S,2S,8aS)-1,2-bis(benzyloxy)-2,3,8,8a-tetrahydroindolizin-7(1H)-one
• 英文别名: (1S,2S,8aS)-1,2-bis(phenylmethoxy)-2,3,8,8a-tetrahydro-1H-indolizin-7-one
• CAS: 1400236-11-4
• 化学式: C₂₂H₂₃NO₃
• 分子量: 349.43
• InChiKey: HURVEQSYKIWTPJ-FKBYEOEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (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 、 1-甲氧基-3-三甲基硅氧基-1,3-丁二烯 在 ytterbium(III) triflate 作用下， 以 二氯甲烷 为溶剂， 反应 3.17h， 以81.818%的产率得到
  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

文献信息

• Synthesis of Polyhydroxylated Quinolizidine and Indolizidine Scaffolds from Sugar-Derived Lactams via a One-Pot Reduction/Mannich/Michael Sequence
  作者：Piotr Szcześniak、Sebastian Stecko、Elżbieta Maziarz、Olga Staszewska-Krajewska、Bartłomiej Furman

  DOI：10.1021/jo502146z

  日期：2014.11.7

  A direct approach to the synthesis of indolizidine and quinolizidine scaffolds of iminosugars is described. The presented strategy is based on a one-pot sugar lactam reduction with Schwartz’s reagent followed by a diastereoselective Mannich/Michael tandem reaction of the resulting sugar imine with Danishefsky’s diene. The stereochemical course of the investigated reaction has been explained in detail

  描述了一种直接合成亚氨基糖的吲哚并立定和喹喔嗪骨架的方法。提出的策略是基于先用Schwartz试剂还原一锅糖内酰胺，然后再将得到的糖亚胺与Danishefsky的二烯进行非对映选择性的Mannich / Michael串联反应。已详细解释了所研究反应的立体化学过程。所获得的双环产物是用于合成各种天然存在的多羟基化生物碱及其衍生物的有吸引力的结构单元。
• 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.