(S)-4-Ethyl-3,6,10-trioxo-3,4,6,7,8,10-hexahydro-1H-pyrano[3,4-f]indolizin-4-yl acetate | 202524-90-1

• 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: (S)-4-Ethyl-3,6,10-trioxo-3,4,6,7,8,10-hexahydro-1H-pyrano[3,4-f]indolizin-4-yl acetate
• 英文别名: [(4S)-4-ethyl-3,6,10-trioxo-7,8-dihydro-1H-pyrano[3,4-f]indolizin-4-yl] acetate
• CAS: 202524-90-1
• 化学式: C₁₅H₁₅NO₆
• 分子量: 305.287
• InChiKey: XGAOUPSDOOVLLF-HNNXBMFYSA-N

物化性质

• 沸点：
  640.9±55.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  90
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-4-Ethyl-3,6,10-trioxo-3,4,6,7,8,10-hexahydro-1H-pyrano[3,4-f]indolizin-4-yl acetate 在 potassium carbonate 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 13.5h， 生成 (19S)-19-ethyl-19-hydroxy-8-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaene-14,18-dione
  参考文献：
  名称：

  Synthesis and absolute configuration of 9-β-D-glucosyloxycamptothecin, a new gluco camptothecin isolated from Ophiorrhiza pumila regenerated plants

  摘要：

  我们合成了 9-δ²-D-Glucosyloxy 喜树碱，并确定了它的结构和绝对构型。

  DOI：

  10.1039/a708263k
• 作为产物：
  描述：

  7-乙基-10-羟基喜树碱中间体 、 乙酰氯 以 neat (no solvent) 为溶剂， 以85%的产率得到(S)-4-Ethyl-3,6,10-trioxo-3,4,6,7,8,10-hexahydro-1H-pyrano[3,4-f]indolizin-4-yl acetate
  参考文献：
  名称：

  Synthesis and absolute configuration of 9-β-D-glucosyloxycamptothecin, a new gluco camptothecin isolated from Ophiorrhiza pumila regenerated plants

  摘要：

  我们合成了 9-δ²-D-Glucosyloxy 喜树碱，并确定了它的结构和绝对构型。

  DOI：

  10.1039/a708263k

文献信息

• S type 2-substituted hydroxy-2-indolidinylbutyric ester compounds and process for preparation thereof
  申请人：TANABE SEIYAKU CO., LTD.

  公开号：US20030135049A1

  公开（公告）日：2003-07-17

  A process for preparing S type 2-substituted hydroxy-2-indolidinylbutyric ester compound [II]: 1 wherein R o is residue of nitrogen-containing fused heterocyclic carboxylic acid having absolute configuration of “R” (in which the nitrogen atom is protected), R1 and R2 are lower alkyl groups, and E is ester residue, which is useful as an intermediate for preparing camptothecin derivatives having antitumor activities, which comprises 2-ethylating 2-substituted hydroxy-2-indolidinylacetic ester compound [I]: 2 wherein the symbols are as defined above.

  一种制备S型2-取代羟基-2-吲哚丁酸酯化合物II的方法：其中Ro是氮杂环羧酸残基，具有“R”的绝对构型（其中氮原子受保护），R1和R2是较低的烷基基团，E是酯残基，该化合物是制备具有抗肿瘤活性的喜树碱衍生物的中间体，包括对2-取代羟基-2-吲哚丁酸乙酯化合物I进行2-乙基化，其中符号如上所定义。
• Stype 2-substituted hydroxy-2-indolidinylbutyric ester compounds and process for preparation thereof
  申请人：Tanabe Seiyaku Co., Ltd.

  公开号：US20020161231A1

  公开（公告）日：2002-10-31

  A process for preparing S type 2-substituted hydroxy-2-indolidinylbutyric ester compound [II]: 1 wherein R o is residue of nitrogen-containing fused heterocyclic carboxylic acid having absolute configuration of “R” (in which the nitrogen atom is protected), R1 and R2 are lower alkyl groups, and E is ester residue, which is useful as an intermediate for preparing camptothecin derivatives having antitumor activities, which comprises 2-ethylating 2-substituted hydroxy-2-indolidinylacetic ester compound [I]: 2 wherein the symbols are as defined above.

  一种制备S型2-取代羟基-2-吲哚丁酸酯化合物II的方法：其中Ro是氮杂环羧酸残基，具有“R”的绝对构型（其中氮原子受保护），R1和R2是低烷基基团，E是酯基残基，可用作制备具有抗肿瘤活性的喜树碱衍生物的中间体，该方法包括对2-取代羟基-2-吲哚乙酸酯化合物I进行2-乙基化，其中符号如上所定义。
• S type 2-substituted hydroxy-2-indolidinylbutyric ester compounds as intermediates for camptothecin derivatives
  申请人：TANABE SEIYAKU CO., LTD.

  公开号：EP0845464A2

  公开（公告）日：1998-06-03

  A process for preparing S type 2-substituted hydroxy-2-indolidinyl-butyric ester compound [II]: wherein R° is residue of nitrogen-containing fused heterocyclic carboxylic acid having absolute configuration of "R"(in which the nitrogen atom is protected), R1 and R2 are lower alkyl group, and E is ester residue, which is useful as an intermediate for preparing camptothecin derivatives having antitumor activities,    comprises 2-ethylating 2-substituted hydroxy-2-indolidinylacetic ester compound [I]: wherein the symbols are as defined above.

  一种制备 S 型 2-取代羟基-2-吲哚烷基丁酸酯化合物的工艺[II]： 其中 R°为绝对构型为 "R"（其中氮原子被保护）的含氮融合杂环羧酸残基，R1 和 R2 为低级烷基，E 为酯残基，可用作制备具有抗肿瘤活性的喜树碱衍生物的中间体、 包括 2-乙基化 2-取代羟基-2-吲哚乙酸酯化合物[I]： 其中符号如上定义。
• S-type 2-substituted hydroxy-2-indolinylbutyric ester compounds and process for preparation thereof
  申请人：TANABE SEIYAKU CO., LTD.

  公开号：EP1236728A2

  公开（公告）日：2002-09-04

  A process for preparing an S type 4-substituted hydroxypyrano-indolidine compound of the formula (VII): wherein R° is a residue of a nitrogen-containing fused heterocyclic carboxylic acid having an absolute configuration of "R" which is obtained by removing hydroxy group from the carboxyl group of said carboxylic acid (in which the nitrogen atom contained in the residue is protected), is described. The process involves reduction, alkanoylation, nitrosation, rearrangement and intramolecular cyclization reactions.

  一种制备式(VII)的 S 型 4-取代羟基吡喃-吲哚化合物的工艺： 其中 R°是绝对构型为 "R "的含氮融合杂环羧酸的残余物，该残余物是通过从所述羧酸的羧基上去除羟基而得到的（其中残余物中所含的氮原子受到保护）。 该过程包括还原、烷酰化、亚硝基化、重排和分子内环化反应。
• Process for the preparation of s-type 4-substituted hydroxypyranoindolidine compounds
  申请人：TANABE SEIYAKU CO., LTD.

  公开号：EP1528062A2

  公开（公告）日：2005-05-04

  A process for preparing an S type 4-substituted hydroxypyrano-indolidine compound of the formula (VII) : wherein Ro is a residue of a nitrogen-containing fused heterocyclic carboxylic acid having an absolute configuration of "R" which is obtained by removing hydroxy group from the carboxyl group of said carboxylic acid (in which the nitrogen atom contained in the residue is protected), is described. The process involves reduction, alkanoylation, nitrosation, rearrangement and intramolecular cyclization reactions.

  一种制备式(VII)的 S 型 4-取代羟基吡喃-吲哚化合物的工艺： 其中，Ro 是绝对构型为 "R "的含氮融合杂环羧酸的残余物，该残余物是通过从所述羧酸的羧基上去除羟基而得到的（其中残余物中所含的氮原子受到保护）。 该过程包括还原、烷酰化、亚硝基化、重排和分子内环化反应。