(+/-)-coronaridine | 467-77-6

• 物质功能分类: 医药中间体 - 原料药中间体
• 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: (+/-)-coronaridine
• 英文别名: methyl (1R,15S,17R,18R)-17-ethyl-3,13-diazapentacyclo[13.3.1.02,10.04,9.013,18]nonadeca-2(10),4,6,8-tetraene-1-carboxylate
• CAS: 467-77-6
• 化学式: C₂₁H₂₆N₂O₂
• 分子量: 338.45
• InChiKey: NVVDQMVGALBDGE-QHJLWRIMSA-N

物化性质

• 熔点：
  92-93 °C
• 沸点：
  488.1±45.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  45.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-coronaridine 在 盐酸 作用下， 以 乙醚 为溶剂， 生成 (+)-coronaridine hydrochloride
  参考文献：
  名称：

  Synthesis of (−)-Pseudotabersonine, (−)-Pseudovincadifformine, and (+)-Coronaridine Enabled by Photoredox Catalysis in Flow

  摘要：

  Natural product modification with photo-redox catalysis allows for mild, chemoselective access to a wide array of related structures in complex areas of chemical space, providing the possibility for novel structural motifs as well as useful quantities of less abundant congeners. While amine additives have been used extensively as stoichiometric electron donors for photocatalysis, the controlled modification of amine substrates through single-electron oxidation is ideal for the synthesis and modification of alkaloids. Here, we report the conversion of the amine (+)-catharanthine into the natural products (-)-pseudotabersonine, (-)-pseudovincadifformine, and (+)-coronaridine utilizing visible light photoredox catalysis.

  DOI：

  10.1021/ja506170g
• 作为产物：
  描述：

  甲基4-甲酰基己酸酯 在 盐酸 、 sodium tetrahydroborate 、 palladium on activated charcoal 、 氢气 、 溶剂黄146 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 水 、 乙腈 、 苯 为溶剂， 反应 9.0h， 生成 (+/-)-coronaridine
  参考文献：
  名称：

  Synthetic noribogaine

  摘要：

  合成诺利波甲碱，最好不含伊博甲碱，并可选择性地含有其他自然存在的泰贝南特伊博加生物碱之一或多个。

  公开号：

  US09617274B1

文献信息

• Enantioselective syntheses of coronaridine and 18-methoxycoronaridine
  作者：Martin E Kuehne、Timothy E Wilson、Upul K Bandarage、Wenning Dai、Qian Yu

  DOI：10.1016/s0040-4020(01)00045-x

  日期：2001.3

  gave diastereoselectively, through a secodine-type intramolecular Diels–Alder reaction, tetracyclic intermediates that could be carried to (−)-coronaridine or to the important anti-addictive (−)-18-methoxycoronaridine. The 2,3-(R)-ferroceno-6,6-dimethyl-1-(S)-cyclohexyl chiral auxiliary was most effective, providing >99% ee of a tetracyclic intermediate after removal of the chiral auxiliary group.

  带有手性N b-取代基的吲哚并氮杂的缩合：1-（R）-萘基-α-乙基，[1-（R）-[（S）-2-（二苯基膦基）二茂铁基]-乙基]或2,3 -（R）-二茂铁-6,6-二甲基-1-（S）-环己基，具有4-（1,3-二氧戊环-2-基）-己醛，或与4-（1,3-二氧戊环-2 -yl）-6-甲氧基己醛，通过苏糖精类型的分子内Diels-Alder反应非对映选择性地产生了可携带至（-）-coronaridine或重要的抗上瘾性（-）-18-甲氧基Coronaridine的四环中间体。2,3-（R）-二茂铁-6,6-二甲基-1-（S）-环己基手性助剂最有效，除去手性助剂基团后可提供> 99％ee的四环中间体。
• Synthetic noribogaine
  申请人：DemeRx, Inc.

  公开号：US09617274B1

  公开（公告）日：2017-04-11

  Synthetic noribogaine preferably free of ibogaine and, optionally, one or more of other naturally occurring Tabernanth iboga alkaloids, is provided.

  合成诺利波甲碱，最好不含伊博甲碱，并可选择性地含有其他自然存在的泰贝南特伊博加生物碱之一或多个。
• Synthesis of (−)-Pseudotabersonine, (−)-Pseudovincadifformine, and (+)-Coronaridine Enabled by Photoredox Catalysis in Flow
  作者：Joel W. Beatty、Corey R. J. Stephenson

  DOI：10.1021/ja506170g

  日期：2014.7.23

  Natural product modification with photo-redox catalysis allows for mild, chemoselective access to a wide array of related structures in complex areas of chemical space, providing the possibility for novel structural motifs as well as useful quantities of less abundant congeners. While amine additives have been used extensively as stoichiometric electron donors for photocatalysis, the controlled modification of amine substrates through single-electron oxidation is ideal for the synthesis and modification of alkaloids. Here, we report the conversion of the amine (+)-catharanthine into the natural products (-)-pseudotabersonine, (-)-pseudovincadifformine, and (+)-coronaridine utilizing visible light photoredox catalysis.