(4R,6R)-4-hydroxy-1-methyl-6-[[(5R,7R)-7-methyl-5,6,7,8-tetrahydroquinolin-5-yl]methyl]piperidin-2-one | 955126-86-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (4R,6R)-4-hydroxy-1-methyl-6-[[(5R,7R)-7-methyl-5,6,7,8-tetrahydroquinolin-5-yl]methyl]piperidin-2-one
• CAS: 955126-86-0
• 化学式: C₁₇H₂₄N₂O₂
• 分子量: 288.39
• InChiKey: JFRRNLWUZFKORK-AAVRWANBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  53.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R,6R)-4-hydroxy-1-methyl-6-[[(5R,7R)-7-methyl-5,6,7,8-tetrahydroquinolin-5-yl]methyl]piperidin-2-one 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 反应 4.5h， 以83%的产率得到lycoposerramine W
  参考文献：
  名称：

  Asymmetric Total Syntheses of Two Phlegmarine-Type Alkaloids, Lycoposerramines-V and -W, Newly Isolated from Lycopodium serratum

  摘要：

  Two new Phlegmarine-type alkaloids, lycoposerramines-V and -W, were isolated from Lycopodium, serratum, and their structures including the absolute configuration were established by asymmetric total synthesis involving such key steps as Johnson-Claisen rearrangement, asymmetric allylation, and ring-closing metathesis (RCM)- or Sml(2)-mediated stereoselective piperidine ring construction.

  DOI：

  10.1021/ol701871v
• 作为产物：
  描述：

  (R)-5-methyl-2-iodo-2-cyclohexen-1-one 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 四氧化锇 sodium hydroxide 、 sodium tetrahydroborate 、 sodium periodate 、 lithium aluminium tetrahydride 、 sodium azide 、 samarium diiodide 、 cerium(III) chloride 、 硼烷四氢呋喃络合物 、 草酰氯 、 四丁基氟化铵 、 水 、 甲氧基胺盐酸盐 、 溶剂黄146 、 二甲基亚砜 、 三乙胺 、 三苯基膦 、 硝苯酚 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 xylene 为溶剂， 反应 103.5h， 生成 (4R,6R)-4-hydroxy-1-methyl-6-[[(5R,7R)-7-methyl-5,6,7,8-tetrahydroquinolin-5-yl]methyl]piperidin-2-one
  参考文献：
  名称：

  Asymmetric Total Syntheses of Two Phlegmarine-Type Alkaloids, Lycoposerramines-V and -W, Newly Isolated from Lycopodium serratum

  摘要：

  Two new Phlegmarine-type alkaloids, lycoposerramines-V and -W, were isolated from Lycopodium, serratum, and their structures including the absolute configuration were established by asymmetric total synthesis involving such key steps as Johnson-Claisen rearrangement, asymmetric allylation, and ring-closing metathesis (RCM)- or Sml(2)-mediated stereoselective piperidine ring construction.

  DOI：

  10.1021/ol701871v

文献信息

• Asymmetric Total Syntheses of Two Phlegmarine-Type Alkaloids, Lycoposerramines-V and -W, Newly Isolated from <i>Lycopodium serratum</i>
  作者：Takahide Shigeyama、Kazuaki Katakawa、Noriyuki Kogure、Mariko Kitajima、Hiromitsu Takayama

  DOI：10.1021/ol701871v

  日期：2007.9.1

  Two new Phlegmarine-type alkaloids, lycoposerramines-V and -W, were isolated from Lycopodium, serratum, and their structures including the absolute configuration were established by asymmetric total synthesis involving such key steps as Johnson-Claisen rearrangement, asymmetric allylation, and ring-closing metathesis (RCM)- or Sml(2)-mediated stereoselective piperidine ring construction.