(-)-(S)-isoverbasikrine | 249739-45-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: (-)-(S)-isoverbasikrine
• 英文别名: (8S)-1-[(Z)-3-(4-methoxyphenyl)prop-2-enoyl]-8-phenyl-1,5,9,13-tetrazacycloheptadecan-6-one
• CAS: 249739-45-5
• 化学式: C₂₉H₄₀N₄O₃
• 分子量: 492.662
• InChiKey: XHTALCPRDZVQLY-LAGAIYJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  36
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  82.7
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (-)-(S)-isoverbasikrine 在 palladium on activated charcoal 氢气 作用下， 反应 6.5h， 以100%的产率得到(8S)-1-[3-(4-methoxyphenyl)propanoyl]-8-phenyl-1,5,9,13-tetraazacycloheptadecan-6-one
  参考文献：
  名称：

  Macrocyclic Spermine Alkaloids fromVerbascum: Isolation, Structure Elucidation, and Syntheses of the (E/Z)-Isomeric Pairs (S)-Verbasikrine/(S)-Isoverbasikrine and (S)-Verbamekrine/(S)-Isoverbamekrine

  摘要：

  The isolation and structure elucidation of the 17-membered macrocyclic spermine alkaloids (S)-verbasikrine (3), (S)-isoverbasikrine (6), (S)-verbamekrine (9), and (S)-isoverbamekrine (12) is presented. The syntheses of their racemates are described. The HPLC/APCI-MS analysis of the original total alkaloid extract of Verbascum pseudonobile is presented.

  DOI：

  10.1002/(sici)1522-2675(19990804)82:8<1185::aid-hlca1185>3.0.co;2-p
• 作为产物：
  描述：

  (+)-(2S)-2-phenyl-1,5,9,14-tetraazabicyclo[12.3.1]octadecan-4-one 在 盐酸羟胺 、 三乙胺 作用下， 以 盐酸 、 甲醇 、 二氯甲烷 为溶剂， 生成 (-)-(S)-isoverbasikrine
  参考文献：
  名称：

  Asymmetric Syntheses of the Macrocyclic Spermine Alkaloids (−)-(S)-Protoverbine, (−)-(S)-Buchnerine, and Their Naturally Occurring Congenial Alkaloids

  摘要：

  Asymmetric syntheses of the following 17-membered macrocyclic spermine alkaloids are presented: (-)-(S)-protoverbine (= (8S)-8-phenyl-1,5,9,13-tetraazacycloheptadecane-6-one; 1), (+)-(S)-protomethine (=(2S)-2-phenyl-1,5,9,14-tetraazabicyclo[12.3.1]octadecan-4-one; 2), (-)-(S)-buchnerine (=(8S)-8-(4-methoxyphenyl)-1,5,9,13-tetraazacycloheptadecane-6-one; 8), (+)-(S)-VeTbamethine (=(-')-(2S)-9-[(E)-phenylprop- 2-enoyl]-2-phenyl-1,5,9,14-tetraazabicyclo[12.3.1]octadecan-4-one; 4), (-)-(S)-verbacine [(E)-phenylprop-2-enoyl]-8-phenyl-1,5,9,13-tetraazacycloheptadecan-6-one; 3), (-)-(S)-verbasikrine (8S)-1-[(E)-3-(4-methoxyphenyl)prop-2-enoyl]-8-phenyl-1,5,9,13-tetraazacycloheptadecan-6-one; 26), (S)-isoverbasikrine (=(-)-(8S)-1-[(Z)-3-(4-methoxyphenyl)prop-2-enoyl]-8-phenyl-1,5,9,13-tetraazacycloheptadecan-6-one; 25), (+)-(S)-verbamekrine (= (+)-(2S)-9-[(E)-3-(4-methoxyphenyl)prop-2-enoyl]-2-phenyl- 1,5,9.14-tetraazabicyclo[12.3.1]octadecan-4- one; 23), and(+)-(S)-isoverbamekrine (=(+)-(2S)-9-[(Z)-3-(4-methoxyphenyl)prop-2-enoyl]-2-phenyl-1,5,9,14-tetraazabicyclo[12.3.1]octadecan-4-one; 24). Effective methods for H-1-NMR determination of the enantiomeric purity in which (S)-2-hydroxy-2-phenylacetic acid and (S)-2-acetoxy-2-phenylacetic acid are used as shift reagents for 1, 8, and related macrocyclic alkaloids are described.

  DOI：

  10.1002/1522-2675(200204)85:4<979::aid-hlca979>3.0.co;2-f

文献信息

• Asymmetric Syntheses of the Macrocyclic Spermine Alkaloids (−)-(S)-Protoverbine, (−)-(S)-Buchnerine, and Their Naturally Occurring Congenial Alkaloids
  作者：Konstantin Drandarov、Armin Guggisberg、Manfred Hesse

  DOI：10.1002/1522-2675(200204)85:4<979::aid-hlca979>3.0.co;2-f

  日期：2002.4

  Asymmetric syntheses of the following 17-membered macrocyclic spermine alkaloids are presented: (-)-(S)-protoverbine (= (8S)-8-phenyl-1,5,9,13-tetraazacycloheptadecane-6-one; 1), (+)-(S)-protomethine (=(2S)-2-phenyl-1,5,9,14-tetraazabicyclo[12.3.1]octadecan-4-one; 2), (-)-(S)-buchnerine (=(8S)-8-(4-methoxyphenyl)-1,5,9,13-tetraazacycloheptadecane-6-one; 8), (+)-(S)-VeTbamethine (=(-')-(2S)-9-[(E)-phenylprop- 2-enoyl]-2-phenyl-1,5,9,14-tetraazabicyclo[12.3.1]octadecan-4-one; 4), (-)-(S)-verbacine [(E)-phenylprop-2-enoyl]-8-phenyl-1,5,9,13-tetraazacycloheptadecan-6-one; 3), (-)-(S)-verbasikrine (8S)-1-[(E)-3-(4-methoxyphenyl)prop-2-enoyl]-8-phenyl-1,5,9,13-tetraazacycloheptadecan-6-one; 26), (S)-isoverbasikrine (=(-)-(8S)-1-[(Z)-3-(4-methoxyphenyl)prop-2-enoyl]-8-phenyl-1,5,9,13-tetraazacycloheptadecan-6-one; 25), (+)-(S)-verbamekrine (= (+)-(2S)-9-[(E)-3-(4-methoxyphenyl)prop-2-enoyl]-2-phenyl- 1,5,9.14-tetraazabicyclo[12.3.1]octadecan-4- one; 23), and(+)-(S)-isoverbamekrine (=(+)-(2S)-9-[(Z)-3-(4-methoxyphenyl)prop-2-enoyl]-2-phenyl-1,5,9,14-tetraazabicyclo[12.3.1]octadecan-4-one; 24). Effective methods for H-1-NMR determination of the enantiomeric purity in which (S)-2-hydroxy-2-phenylacetic acid and (S)-2-acetoxy-2-phenylacetic acid are used as shift reagents for 1, 8, and related macrocyclic alkaloids are described.
• Macrocyclic Spermine Alkaloids fromVerbascum: Isolation, Structure Elucidation, and Syntheses of the (E/Z)-Isomeric Pairs (S)-Verbasikrine/(S)-Isoverbasikrine and (S)-Verbamekrine/(S)-Isoverbamekrine
  作者：Nikolay Youhnovski、Konstantin Drandarov、Armin Guggisberg、Manfred Hesse

  DOI：10.1002/(sici)1522-2675(19990804)82:8<1185::aid-hlca1185>3.0.co;2-p

  日期：1999.8.4

  The isolation and structure elucidation of the 17-membered macrocyclic spermine alkaloids (S)-verbasikrine (3), (S)-isoverbasikrine (6), (S)-verbamekrine (9), and (S)-isoverbamekrine (12) is presented. The syntheses of their racemates are described. The HPLC/APCI-MS analysis of the original total alkaloid extract of Verbascum pseudonobile is presented.