(S)-4-ethyl-4-hydroxy-6-iodo-7-(pent-2-yn-1-yl)-1,7-dihydro-3H-pyrano[3,4-c]pyridino-3,8(4H)-dione | 174092-83-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃吡啶类
• 英文名称: (S)-4-ethyl-4-hydroxy-6-iodo-7-(pent-2-yn-1-yl)-1,7-dihydro-3H-pyrano[3,4-c]pyridino-3,8(4H)-dione
• 英文别名: (S)-4-Ethyl-4-hydroxy-6-iodo-3-oxo-7-(2-pentynyl)-1H-pyrano[3,4-c]-8-pyridone；(4S)-4-ethyl-4-hydroxy-6-iodo-7-pent-2-ynyl-1H-pyrano[3,4-c]pyridine-3,8-dione
• CAS: 174092-83-2
• 化学式: C₁₅H₁₆INO₄
• 分子量: 401.201
• InChiKey: VXMFKFSRILSVLS-HNNXBMFYSA-N

物化性质

• 沸点：
  618.6±55.0 °C(Predicted)
• 密度：
  1.72±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-4-ethyl-4-hydroxy-6-iodo-7-(pent-2-yn-1-yl)-1,7-dihydro-3H-pyrano[3,4-c]pyridino-3,8(4H)-dione 在 tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate 、 氢溴酸 、 potassium carbonate 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 24.0h， 生成 7-乙基-10-羟基喜树碱
  参考文献：
  名称：

  可见光诱导的自由基级联环化：（20S）-喜树碱，SN-38和伊立替康的合成

  摘要：

  （20 S）-喜树碱，伊立替康和SN-38是在可见光下用钌催化剂通过N-炔丙基碘吡啶并酮和芳基异腈通过光催化的自由基级联环化反应成功合成的。这种合成方法在不使用重金属试剂的情况下，在温和的反应条件下，以高收率组成了喜树碱类抗肿瘤药家族，提供了有用的途径。

  DOI：

  10.1002/cjoc.201800358
• 作为产物：
  描述：

  4-Ethyl-8-methoxy-6-trimethylsilanyl-1H-pyrano[3,4-c]pyridine 在 四氧化锇 、 hydroquinindine-2,5-diphenyl-4,6-pyrimidinediyl diether 、 氢碘酸 、 碘 、 一氯化碘 、 sodium hydride 、 calcium carbonate 、 lithium bromide 作用下， 以 乙二醇二甲醚 、 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-4-ethyl-4-hydroxy-6-iodo-7-(pent-2-yn-1-yl)-1,7-dihydro-3H-pyrano[3,4-c]pyridino-3,8(4H)-dione
  参考文献：
  名称：

  Curran, Dennis P.; Ko, Sung-Bo; Josien, Hubert, Angewandte Chemie, 1995, vol. 107, # 23/24, p. 2948 - 2950

  摘要：

  DOI：

文献信息

• Novel intermediates in the synthesis of camptothecin and related compounds and synthesis thereof
  申请人：——

  公开号：US20010029298A1

  公开（公告）日：2001-10-11

  The present invention provides a short, convergent total synthesis of camptothecin and related compounds which consists of a novel 4+1 radical annulation. The present invention also provides novel chemical intermediates for such 4+1 radical annulations.

  本发明提供了一种喜树碱及相关化合物的简短、趋同的全合成方法，该方法包括一种新型的 4+1 自由基环化反应。本发明还提供了用于此类 4+1 自由基环化的新型化学中间体。
• A General Synthetic Approach to the (20S)-Camptothecin Family of Antitumor Agents by a Regiocontrolled Cascade Radical Cyclization of Aryl Isonitriles
  作者：Hubert Josien、Sung-Bo Ko、David Bom、Dennis P. Curran

  DOI：10.1002/(sici)1521-3765(199801)4:1<67::aid-chem67>3.0.co;2-f

  日期：1998.1

  A general and efficient synthesis of (20S)-camptothecin (1a) is reported. A key common intermediate containing the pyridone and lactone (DE) rings of camptothecin and most derivatives was constructed from 2-trimethylsilyl-6-methoxypyridine by a series of metalation reactions and a Heck cyclization to provide an achiral bicyclic enol ether. Sharpless asymmetric dihydroxylation followed by lactol oxidation and iododesilylation produced the key intermediate in 94% enantiomeric excess. Alkylation with propargyl bromide and a cascade radical reaction with phenyl isonitrile then produced 1a. About 20 other penta- and hexacyclic analogues of camptothecin with differing single or multiple substituents at C7, C9, C10, C11, and/or C12 were made by changing the propargylating agent and the isonitrile. Included among these are several drug candidates and the approved drugs topotecan and irinotecan. The synthesis of the prodrug irinotecan is direct one that does not pass through the active metabolite. The use of ortho-trimethylsilyl-substituted isonitriles allows the regioselective synthesis of camptothecin analogues in cases where isomeric mixtures are formed from the parent isonitriles. The synthesis of the derivatives relies on the broad scope and functional group tolerance of the key cascade radical reaction.
• Method of synthesizing camptothecin-relating compounds
  申请人：Ogawa Takanori

  公开号：US20070010674A1

  公开（公告）日：2007-01-11

  The present invention is to prepare efficiently 2′-amino-5′-hydroxypropiophenone corresponding to the AB-ring part of camptothecin (CPT) skeleton and a tricyclic ketone corresponding to the CDE-ring part in order to provide efficiently CPT by the total synthesis, which is a starting material for irinotecan hydrochloride and various kinds of camptothecin derivatives, and to provide stably CPT and its derivatives.
• US6252079B1
  申请人：——

  公开号：US6252079B1

  公开（公告）日：2001-06-26
• US6620937B2
  申请人：——

  公开号：US6620937B2

  公开（公告）日：2003-09-16