(S)-4-ethyl-4-hydroxy-6-iodo-8-methoxy-1,4-dihydro-pyrano[3,4-c]pyridin-3-one | 174092-79-6

• 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-8-methoxy-1,4-dihydro-pyrano[3,4-c]pyridin-3-one
• 英文别名: (4S)-4-ethyl-4-hydroxy-6-iodo-8-methoxy-1H-pyrano[3,4-c]pyridin-3-one
• CAS: 174092-79-6
• 化学式: C₁₁H₁₂INO₄
• 分子量: 349.125
• InChiKey: QITVYQRBHQNUFA-NSHDSACASA-N

物化性质

• 沸点：
  490.9±45.0 °C(Predicted)
• 密度：
  1.780±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  68.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-4-ethyl-4-hydroxy-6-iodo-8-methoxy-1,4-dihydro-pyrano[3,4-c]pyridin-3-one 在 氢碘酸 、 六甲基二锡 、 sodium hydride 、 lithium bromide 作用下， 以 乙二醇二甲醚 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 生成 喜树碱
  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：
• 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 、 碘 、 一氯化碘 、 calcium carbonate 作用下， 生成 (S)-4-ethyl-4-hydroxy-6-iodo-8-methoxy-1,4-dihydro-pyrano[3,4-c]pyridin-3-one
  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

• Intermediates in the synthesis of camptothecin and related compounds and synthesis thereof
  申请人：University of Pittsburgh

  公开号：US06252079B1

  公开（公告）日：2001-06-26

  The present invention provides a short, convergent total synthesis of irinotecan and derivative compounds which comprises of a novel 4+1 radical annulation wherein the precursor is reacted with an aryl isonitrile having the formula wherein X is Br or I, and R4 is an alkyl group, an allyl group, a propargyl group or a benzyl group, and R16 is H, a C1-C6 alkoxy group, a group wherein p is an integer between 4 and 12, or a C1-C12 acyclic dialkylamino group. The present invention also provides novel chemical intermediates for such 4+1 radical annulations.

  本发明提供了伊立替康及其衍生化合物的短、收敛的全合成方法，包括一种新颖的4+1自由基环合反应，其中前体物质与具有以下结构的芳基异腈发生反应：其中X为Br或I，R4为烷基、烯丙基、丙炔基或苄基，R16为H、C1-C6烷氧基、p为4至12之间的整数的羟基，或C1-C12非环二烷基氨基基团。本发明还提供了用于这种4+1自由基环合反应的新型化学中间体。
• Catalytic Enantioselective Synthesis of (20S)-Camptothecin Intermediates Using Cyanosilylation of Ketones Promoted by D-Glucose-derived Lanthanide Catalyst
  作者：Masakatsu Shibasaki、Kazuo Yabu、Shuji Masumoto、Motomu Kanai、Wu Du、Dennis P. Curran

  DOI：10.3987/com-02-s49

  日期：——

  An efficient catalytic enantioselective synthetic route was developed for Curran's versatile camptothecin intermediate (5). The key step is the catalytic enantioselective cyanosilylation of ketone (7) using a chiral samarium (Sm) complex. The target ketone cyanohydrin (6) was obtained with 90% ee using 2 mol % of the catalyst. A gadolinium (Gd) complex derived from the same chiral ligand could also

  为 Curran 的多功能喜树碱中间体 (5) 开发了一种有效的催化对映选择性合成路线。关键步骤是使用手性钐 (Sm) 配合物对酮 (7) 进行催化对映选择性氰基化。使用 2 mol% 的催化剂获得目标酮合氰化氢 (6)，ee 为 90%。源自相同手性配体的钆 (Gd) 配合物也可用作对映选择性催化剂以合成 Corey 的中间体 (11)。
• Studies toward practical synthesis of (20S)-camptothecin family through catalytic enantioselective cyanosilylation of ketones: improved catalyst efficiency by ligand-tuning
  作者：Kazuo Yabu、Shuji Masumoto、Motomu Kanai、Dennis P. Curran、Masakatsu Shibasaki

  DOI：10.1016/s0040-4039(02)00451-3

  日期：2002.4

  Enantioselective catalyst efficiency for the synthesis of the camptothecin family was improved through ligand-tuning. Key intermediates of two convergent syntheses of camptothecin (Curran's intermediate and Corey's intermediate) were obtained in up to 10 g scale through the catalytic enantioselective cyanosilylation of ketones.

  通过调节配体提高了喜树碱家族合成的对映选择性催化剂的效率。通过酮的催化对映选择性氰基硅烷化，喜树碱的两种聚合合成的关键中间体（Curran's中间体和Corey's中间体）以高达10 g的规模获得。
• Process for producing tricyclic ketone
  申请人：Nishiyama Hiroyuki

  公开号：US20090023927A1

  公开（公告）日：2009-01-22

  In order to efficiently supply CPT, which is a starting compound of irinotecan hydrochloride and a variety of camptothecin derivatives, by a practical total synthesis, the invention provides a means of efficiently preparing a tricyclic ketone that corresponds to a CDE ring moiety of a camptothecin (CPT) skeleton.

  为了通过实际的全合成高效地供应伊立替康盐酸盐的起始化合物CPT和各种喜树碱衍生物，本发明提供了一种有效制备对应于喜树碱（CPT）骨架中的CDE环部分的三环酮的方法。
• PROCESS FOR PRODUCING TRICYCLIC KETONE
  申请人：Nishiyama Hiroyuki

  公开号：US20120041204A1

  公开（公告）日：2012-02-16

  In order to efficiently supply CPT, which is a starting compound of irinotecan hydrochloride and a variety of camptothecin derivatives, by a practical total synthesis, the invention provides a means of efficiently preparing a tricyclic ketone that corresponds to a CDE ring moiety of a camptothecin (CPT) skeleton.

  为了通过实用的全合成方法高效地合成伊立替康盐酸盐和多种喜树碱衍生物的起始化合物CPT，本发明提供了一种有效制备与喜树碱（CPT）骨架的CDE环部分相应的三环酮的方法。