phlegmariurine A | 93754-82-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: phlegmariurine A
• 英文别名: (1S,6R)-6-methyl-9-azatricyclo[7.4.3.04,13]hexadec-4(13)-ene-2,8-dione
• CAS: 93754-82-6
• 化学式: C₁₆H₂₃NO₂
• 分子量: 261.364
• InChiKey: OFVBIHDTBLOLMM-RISCZKNCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  phlegmariurine A 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 生成 (1S,2R,6R)-2-Hydroxy-6-methyl-9-aza-tricyclo[7.4.3.0^4,13]hexadec-4(13)-en-8-one
  参考文献：
  名称：

  Seven new Lycopodium alkaloids, lycoposerramines-C, -D, -E, -P, -Q, -S, and -U, from Lycopodium serratum Thunb.

  摘要：

  Seven new alkaloids, lycoposerramines-C, -D, -E, -P, -Q, -S, and -U, having novel fawcettimine-related structures, were isolated front the club moss Lycopodium serratum Thunb. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02026-9
• 作为产物：
  描述：

  lycoposerramine-C 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以95%的产率得到phlegmariurine A
  参考文献：
  名称：

  First Asymmetric Total Syntheses of Fawcettimine-Type Lycopodium Alkaloids, Lycoposerramine-C and Phlegmariurine-A

  摘要：

  A successful asymmetric total synthesis of lycoposerramine-C involving such key steps as a cobalt-mediated Pauson-Khand reaction and vinyl Claisen rearrangement and its biomimetic transformation to phlegmariurine-A are described.

  DOI：

  10.1021/ol902437t

文献信息

• First Asymmetric Total Syntheses of Fawcettimine-Type <i>Lycopodium</i> Alkaloids, Lycoposerramine-C and Phlegmariurine-A
  作者：Atsushi Nakayama、Noriyuki Kogure、Mariko Kitajima、Hiromitsu Takayama

  DOI：10.1021/ol902437t

  日期：2009.12.3

  A successful asymmetric total synthesis of lycoposerramine-C involving such key steps as a cobalt-mediated Pauson-Khand reaction and vinyl Claisen rearrangement and its biomimetic transformation to phlegmariurine-A are described.
• Seven new Lycopodium alkaloids, lycoposerramines-C, -D, -E, -P, -Q, -S, and -U, from Lycopodium serratum Thunb.
  作者：Hiromitsu Takayama、Kazuaki Katakawa、Mariko Kitajima、Kentaro Yamaguchi、Norio Aimi

  DOI：10.1016/s0040-4039(02)02026-9

  日期：2002.11

  Seven new alkaloids, lycoposerramines-C, -D, -E, -P, -Q, -S, and -U, having novel fawcettimine-related structures, were isolated front the club moss Lycopodium serratum Thunb. (C) 2002 Elsevier Science Ltd. All rights reserved.