(1S,2R,8aS)-1,2-Bis-benzyloxy-5-hydroxy-hexahydro-indolizin-3-one | 342008-05-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚里西啶
• 英文名称: (1S,2R,8aS)-1,2-Bis-benzyloxy-5-hydroxy-hexahydro-indolizin-3-one
• 英文别名: (1S,2R,8aS)-5-hydroxy-1,2-bis(phenylmethoxy)-2,5,6,7,8,8a-hexahydro-1H-indolizin-3-one
• CAS: 342008-05-3
• 化学式: C₂₂H₂₅NO₄
• 分子量: 367.445
• InChiKey: AABJEDAIBBWXKS-UDEWTMQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,2R,8aS)-1,2-Bis-benzyloxy-5-hydroxy-hexahydro-indolizin-3-one 在 钯 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 甲醇 、 甲酸 、 二氯甲烷 为溶剂， 生成 (1S,2R,8aS)-hexahydro-1,2-dihydroxyindolizin-3(5H)-one
  参考文献：
  名称：

  SmI2-mediated hetero-coupling reaction of lactams with aldehydes; synthesis of indolizidine alkaloids, (−)-δ-coniceine, (+)-5-epiindolizidine 167B and (+)-lentiginosine

  摘要：

  Treatment of alicyclic and aromatic lactams with several aldehydes in the presence of samarium(II) diiodide was found to undergo a novel nitrogen-carbon (hetero) coupling reaction to generate N-alpha -hydroxyalkylated lactams in high yield. The chiral lactams with an aldehyde-side chain incorporating the L-pyroglutamic acid- or L-tartaric acid-derived skeleton also reacted intramolecularly under the same conditions to afford the corresponding bicyclic coupling products, which were further applied to the convenient syntheses of (-)-delta -coniceine, (+)-5-epiindolizidine 167B and (+)-lentiginosine, respectively. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00214-3
• 作为产物：
  描述：

  (3R,4S,5S)-1-(4-Methoxy-benzyl)-5-pent-4-enyl-3,4-bis-triisopropylsilanyloxy-pyrrolidin-2-one 在 三氢化钐 、 ammonium cerium(IV) nitrate 、 二碘甲烷 、 四丁基氟化铵 、 silver(l) oxide 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 、 乙腈 为溶剂， 生成 (1S,2R,8aS)-1,2-Bis-benzyloxy-5-hydroxy-hexahydro-indolizin-3-one
  参考文献：
  名称：

  SmI2-mediated hetero-coupling reaction of lactams with aldehydes; synthesis of indolizidine alkaloids, (−)-δ-coniceine, (+)-5-epiindolizidine 167B and (+)-lentiginosine

  摘要：

  Treatment of alicyclic and aromatic lactams with several aldehydes in the presence of samarium(II) diiodide was found to undergo a novel nitrogen-carbon (hetero) coupling reaction to generate N-alpha -hydroxyalkylated lactams in high yield. The chiral lactams with an aldehyde-side chain incorporating the L-pyroglutamic acid- or L-tartaric acid-derived skeleton also reacted intramolecularly under the same conditions to afford the corresponding bicyclic coupling products, which were further applied to the convenient syntheses of (-)-delta -coniceine, (+)-5-epiindolizidine 167B and (+)-lentiginosine, respectively. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00214-3

文献信息

• SmI2-mediated hetero-coupling reaction of lactams with aldehydes; synthesis of indolizidine alkaloids, (−)-δ-coniceine, (+)-5-epiindolizidine 167B and (+)-lentiginosine
  作者：Hidemi Yoda、Hideaki Katoh、Yasuaki Ujihara、Kunihiko Takabe

  DOI：10.1016/s0040-4039(01)00214-3

  日期：2001.3

  Treatment of alicyclic and aromatic lactams with several aldehydes in the presence of samarium(II) diiodide was found to undergo a novel nitrogen-carbon (hetero) coupling reaction to generate N-alpha -hydroxyalkylated lactams in high yield. The chiral lactams with an aldehyde-side chain incorporating the L-pyroglutamic acid- or L-tartaric acid-derived skeleton also reacted intramolecularly under the same conditions to afford the corresponding bicyclic coupling products, which were further applied to the convenient syntheses of (-)-delta -coniceine, (+)-5-epiindolizidine 167B and (+)-lentiginosine, respectively. (C) 2001 Elsevier Science Ltd. All rights reserved.