(1S,2S,3R,7R,8R)-3-[(4-methoxyphenoxy)methyl]-2-phenylmethoxy-2,3,5,6,7,8-hexahydro-1H-pyrrolizine-1,7-diol | 873014-45-0

• 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,3R,7R,8R)-3-[(4-methoxyphenoxy)methyl]-2-phenylmethoxy-2,3,5,6,7,8-hexahydro-1H-pyrrolizine-1,7-diol
• CAS: 873014-45-0
• 化学式: C₂₂H₂₇NO₅
• 分子量: 385.46
• InChiKey: NGHGWPOYFIWWJE-YXIAPDDASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  71.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1S,2S,3R,7R,8R)-3-[(4-methoxyphenoxy)methyl]-2-phenylmethoxy-2,3,5,6,7,8-hexahydro-1H-pyrrolizine-1,7-diol 在 palladium on activated charcoal ammonium cerium(IV) nitrate 、 氢气 作用下， 以 水 、 乙腈 、 甲醇 为溶剂， 以80%的产率得到1,2,7-triepi-australine hydrochloride
  参考文献：
  名称：

  A general asymmetric route for the synthesis of the alexine and australine family of pyrrolizidine alkaloids. The first asymmetric synthesis of 1,2-diepi-alexine and 1,2,7-triepi-australine

  摘要：

  The first asymmetric synthesis of 1,2-diepi-alexine and 1,2,7-triepi-australine (both are unknown at present) is described, which utilized the regioselective asymmetric aminohydroxylation (RAA) reaction of the achiral olefin VI, the cross metathesis (CM) reaction of the terminal olefin 8, and the formation and subsequent intramolecular double cyclization (DC) reactions of the epoxides 10 and 11. The C1 stereocenter was diastereoselectively introduced by the reaction of the aldehyde 7 with vinylmagnesium bromide. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.10.074
• 作为产物：
  描述：

  ethyl (2E)-4-(4-methoxyphenoxy)but-2-enoate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 bis(acetylacetonate)oxovanadium 盐酸 、 叔丁基过氧化氢 、 lithium hydroxide 、 potassium osmate(VI) 、 sodium hydride 、 二异丁基氢化铝 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 叔丁醇 为溶剂， 反应 33.0h， 生成 (1S,2S,3R,7R,8R)-3-[(4-methoxyphenoxy)methyl]-2-phenylmethoxy-2,3,5,6,7,8-hexahydro-1H-pyrrolizine-1,7-diol
  参考文献：
  名称：

  A general asymmetric route for the synthesis of the alexine and australine family of pyrrolizidine alkaloids. The first asymmetric synthesis of 1,2-diepi-alexine and 1,2,7-triepi-australine

  摘要：

  The first asymmetric synthesis of 1,2-diepi-alexine and 1,2,7-triepi-australine (both are unknown at present) is described, which utilized the regioselective asymmetric aminohydroxylation (RAA) reaction of the achiral olefin VI, the cross metathesis (CM) reaction of the terminal olefin 8, and the formation and subsequent intramolecular double cyclization (DC) reactions of the epoxides 10 and 11. The C1 stereocenter was diastereoselectively introduced by the reaction of the aldehyde 7 with vinylmagnesium bromide. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.10.074