(1R,4S,7R,8S)-1,4,11,11-tetramethyl-4-(hydroxymethyl)-6-oxa-3-aza-tricyclo[6.2.1.0^2,7]undec-2-en-5-one | 1059607-17-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R,4S,7R,8S)-1,4,11,11-tetramethyl-4-(hydroxymethyl)-6-oxa-3-aza-tricyclo[6.2.1.0^2,7]undec-2-en-5-one
• 英文别名: (1S,2R,5S,8R)-5-(hydroxymethyl)-5,8,11,11-tetramethyl-3-oxa-6-azatricyclo[6.2.1.02,7]undec-6-en-4-one
• CAS: 1059607-17-8
• 化学式: C₁₄H₂₁NO₃
• 分子量: 251.326
• InChiKey: GYPQGDBZGICFSS-ZHMYYEFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  58.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,4S,7R,8S)-1,4,11,11-tetramethyl-4-(hydroxymethyl)-6-oxa-3-aza-tricyclo[6.2.1.0^2,7]undec-2-en-5-one 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以92%的产率得到2-甲基-L-丝氨酸
  参考文献：
  名称：

  A concise synthesis of (+)-conagenin and its isomer using chiral tricyclic iminolactones

  摘要：

  An efficient synthesis of (+)-conagenin, a novel immunomodulator produced by Streptomyces roseosporus, has been achieved via the shortest route at present. At the same time, 2-epiconagenin was synthesized according to the same methodology. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.06.033
• 作为产物：
  描述：

  聚合甲醛 、 (1S,2R,5S,8R)-5,8,11,11-tetramethyl-3-oxa-6-aza-tricyclo[6.2.1.0^2,7]undec-6-en-4-one 在 lithium diisopropyl amide 、 N,N-二甲基丙烯基脲 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成 (1R,4R,7R,8S)-1,4,11,11-tetramethyl-4-(hydroxymethyl)-6-oxa-3-aza-tricyclo[6.2.1.0^2,7]undec-2-en-5-one 、 (1R,4S,7R,8S)-1,4,11,11-tetramethyl-4-(hydroxymethyl)-6-oxa-3-aza-tricyclo[6.2.1.0^2,7]undec-2-en-5-one
  参考文献：
  名称：

  A concise synthesis of (+)-conagenin and its isomer using chiral tricyclic iminolactones

  摘要：

  An efficient synthesis of (+)-conagenin, a novel immunomodulator produced by Streptomyces roseosporus, has been achieved via the shortest route at present. At the same time, 2-epiconagenin was synthesized according to the same methodology. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.06.033

文献信息

• A concise synthesis of (+)-conagenin and its isomer using chiral tricyclic iminolactones
  作者：Hai-Fei Wang、Guo-Hua Ma、Shao-Bo Yang、Rong-Gang Han、Peng-Fei Xu

  DOI：10.1016/j.tetasy.2008.06.033

  日期：2008.7

  An efficient synthesis of (+)-conagenin, a novel immunomodulator produced by Streptomyces roseosporus, has been achieved via the shortest route at present. At the same time, 2-epiconagenin was synthesized according to the same methodology. (C) 2008 Elsevier Ltd. All rights reserved.