(E)-6-benzylidene-4-ethyl-3,10-dioxo-3,4,6,7,8,10-hexahydro-1H-pyrano[3,4-f]indolizine-5-carboxylic acid | 145474-13-1

• 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: (E)-6-benzylidene-4-ethyl-3,10-dioxo-3,4,6,7,8,10-hexahydro-1H-pyrano[3,4-f]indolizine-5-carboxylic acid
• 英文别名: (6E)-6-benzylidene-4-ethyl-3,10-dioxo-1,4,7,8-tetrahydropyrano[3,4-f]indolizine-5-carboxylic acid
• CAS: 145474-13-1
• 化学式: C₂₁H₁₉NO₅
• 分子量: 365.386
• InChiKey: QHTXMBPXLGWXNV-JLHYYAGUSA-N

物化性质

• 沸点：
  662.2±55.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  83.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (E)-6-benzylidene-4-ethyl-3,10-dioxo-3,4,6,7,8,10-hexahydro-1H-pyrano[3,4-f]indolizine-5-carboxylic acid 在 三甲基氯硅烷 、 过氧化氢异丙苯 、 C₂₇H₃₃F₆N₇O₂*ClH 、 氢溴酸 、 氧气 、 potassium carbonate 、 臭氧 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 5.75h， 生成 喜树碱
  参考文献：
  名称：

  An improved synthesis of (20 S )-camptothecin and its analogue via an asymmetric α-hydroxylation with a chiral organocatalyst

  摘要：

  An efficient and stereocontrolled synthesis of (20S)-camptothecin and an analogue has been developed. The key feature of this synthesis is the organocatalyzed asymmetric alpha-hydroxylation of the lactone precursor 4 to construct its stereocenter, providing tricyclic hydroxylactone 2 in 90% yield and with 88% enantioselectivity. The precursor 4 was efficiently synthesized from the known pyridine 5 in three steps. (C) 2017 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2017.04.013
• 作为产物：
  描述：

  methyl 7-[1-(methoxycarbonyl)propyl]-5-oxo-1,2,3,5-tetrahydroindolizine-8-carboxylate 在 盐酸 、 苄基三乙基氯化铵 、 水 、 sodium hexamethyldisilazane 、 溶剂黄146 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.0h， 生成 (E)-6-benzylidene-4-ethyl-3,10-dioxo-3,4,6,7,8,10-hexahydro-1H-pyrano[3,4-f]indolizine-5-carboxylic acid
  参考文献：
  名称：

  An improved synthesis of (20 S )-camptothecin and its analogue via an asymmetric α-hydroxylation with a chiral organocatalyst

  摘要：

  An efficient and stereocontrolled synthesis of (20S)-camptothecin and an analogue has been developed. The key feature of this synthesis is the organocatalyzed asymmetric alpha-hydroxylation of the lactone precursor 4 to construct its stereocenter, providing tricyclic hydroxylactone 2 in 90% yield and with 88% enantioselectivity. The precursor 4 was efficiently synthesized from the known pyridine 5 in three steps. (C) 2017 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2017.04.013

文献信息

• Concise total syntheses of dl-camptothecin and related anticancer drugs
  作者：Wang Shen、Craig A. Coburn、William G. Bornmann、Samuel J. Danishefsky

  DOI：10.1021/jo00055a012

  日期：1993.1
• An improved synthesis of (20 S )-camptothecin and its analogue via an asymmetric α-hydroxylation with a chiral organocatalyst
  作者：Xinlong Wang、Lingjun Xu、Fangjun Xiong、Yan Wu、Fener Chen

  DOI：10.1016/j.tetasy.2017.04.013

  日期：2017.6

  An efficient and stereocontrolled synthesis of (20S)-camptothecin and an analogue has been developed. The key feature of this synthesis is the organocatalyzed asymmetric alpha-hydroxylation of the lactone precursor 4 to construct its stereocenter, providing tricyclic hydroxylactone 2 in 90% yield and with 88% enantioselectivity. The precursor 4 was efficiently synthesized from the known pyridine 5 in three steps. (C) 2017 Published by Elsevier Ltd.