3β-cyanocatharanthine | 300535-95-9

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 依波格型生物碱
• 英文名称: 3β-cyanocatharanthine
• 英文别名: methyl (1R,14R,15R,18R)-14-cyano-17-ethyl-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4,6,8,16-pentaene-1-carboxylate
• CAS: 300535-95-9
• 化学式: C₂₂H₂₃N₃O₂
• 分子量: 361.444
• InChiKey: WVSGKIKOIAXKPW-NHRVCYDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  69.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3β-cyanocatharanthine 在 三甲基氰硅烷 、 氧气 、 tetraphenylporphyrin 作用下， 以 二氯甲烷 为溶剂， 反应 1.25h， 以74%的产率得到3β-cyano-7β-hydroxyindolenine catharanthine
  参考文献：
  名称：

  A Singlet Oxygen Mediated New Access to Hydroxyindolenine-Catharanthine Derivatives by Two Sequential Oxidations

  摘要：

  Formation of hydroxyindolenine derivatives by photoinduced oxidation by singlet oxygen of intermediate 3 beta -cyanocatharanthine (3) allows us to synthesize under mild conditions new alkaloids derivatives, 3 beta -cyano-7 beta -hydroxyindolenine-catharanthine (5), 3 beta -cyano-7 beta -hydroxyindolinecatharanthine (6) and 7 beta -hydroxy-indolenine-catharanthine (7), bearing protected indole moities.

  DOI：

  10.3987/com-00-9138
• 作为产物：
  描述：

  3β-cyano-7β-hydroxyindolenine catharanthine 在 sodium tetrahydroborate 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 73.5h， 生成 3β-cyanocatharanthine
  参考文献：
  名称：

  A Singlet Oxygen Mediated New Access to Hydroxyindolenine-Catharanthine Derivatives by Two Sequential Oxidations

  摘要：

  Formation of hydroxyindolenine derivatives by photoinduced oxidation by singlet oxygen of intermediate 3 beta -cyanocatharanthine (3) allows us to synthesize under mild conditions new alkaloids derivatives, 3 beta -cyano-7 beta -hydroxyindolenine-catharanthine (5), 3 beta -cyano-7 beta -hydroxyindolinecatharanthine (6) and 7 beta -hydroxy-indolenine-catharanthine (7), bearing protected indole moities.

  DOI：

  10.3987/com-00-9138

文献信息

• Photosensitized oxidation, by single-electron transfer, of catharanthine and vindoline: a highly regio- and diastereoselective photocyanation reaction
  作者：Guillaume Cocquet、Patrice Rool、Clotilde Ferroud

  DOI：10.1039/b001114m

  日期：——

  The irradiation, by visible light, of (+)-catharanthine 1 and of (−)-16-O-acetylvindoline 5 in the presence of cyanide ion and a catalytic amount of a photosensitizer known to produce singlet oxygen leads to (+)-3β-cyanocatharanthine 3 and the new (−)-16-O-acetyl-3α-cyanovindoline 6. The complete stereostructural identification of these compounds has been ascertained by an accurate spectroscopic survey. High regio- and diastereoselectivities (de > 99%) are observed. Some experiments have been performed which confirm unambiguously that singlet oxygen is the oxidizing species in such photochemical conditions.

  在氰化物离子和催化量的已知可产生单线态氧的光敏剂存在下，通过可见光照射 (+)-长春质 1 和 (−)-16-O-乙酰基文多啉 5，产生 (+)- 3β-氰基长质素 3 和新的 (−)-16-O-乙酰基-3α-氰基维多啉 6。这些化合物的完整立体结构鉴定已通过精确的光谱测量确定。观察到高区域选择性和非对映选择性 (de > 99%)。已经进行的一些实验明确证实单线态氧是这种光化学条件下的氧化物质。
• A catalytic versus stoichiometric photoinduced electron transfer promoted selective C16C21 bond cleavage of catharanthine
  作者：Guillaume Cocquet、Patrice Rool、Clotilde Ferroud

  DOI：10.1016/s0040-4039(00)02117-1

  日期：2001.1

  A clean and efficient access to the cleavamine skeleton is described through the selective oxidative C-16-C-21 bond cleavage of catharanthine. The best result is obtained by the use of catalytic quantities of beta -lapachone as photosensitizer. which permits the successful control of competition between the back electron transfer. the deprotonation and the fragmentation pathway. (C) 2001 Elsevier Science Ltd. All rights reserved.