(3S,6S,8S,8aS)-6-azido-8-methoxy-6-methyl-5-oxo-octahydroindolizine-3-carboxylic acid methyl ester | 743423-49-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3S,6S,8S,8aS)-6-azido-8-methoxy-6-methyl-5-oxo-octahydroindolizine-3-carboxylic acid methyl ester
• 英文别名: methyl (3S,6S,8S,8aS)-6-azido-8-methoxy-6-methyl-5-oxo-1,2,3,7,8,8a-hexahydroindolizine-3-carboxylate
• CAS: 743423-49-6
• 化学式: C₁₂H₁₈N₄O₄
• 分子量: 282.299
• InChiKey: PNATWXHRHXWDSJ-PEFMBERDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3S,6S,8S,8aS)-6-azido-8-methoxy-6-methyl-5-oxo-octahydroindolizine-3-carboxylic acid methyl ester 在 palladium on activated charcoal lithium hydroxide 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 56.0h， 生成 (3S,6S,8S,8aS)-6-acetylamino-8-methoxy-6-methyl-5-oxo-octahydroindolizine-3-carboxylic acid
  参考文献：
  名称：

  Synthesis of 3₁₀-Helix-Inducing Constrained Analogues of l-Proline

  摘要：

  A bicyclic indolizidinone carboxylic acid and a tricyclic constrained analogue Of L-proline were synthesized and evaluated for their ability to induce helix formation as L-Ala tetrapeptides. Variable-temperature NMR, DMSO titration, CD spectra, and X-ray structure analyses, in conjunction with molecular modeling, confirmed the existence of 3(10)-helical motifs with di- and tetrapeptides Of L-Ala.

  DOI：

  10.1021/jo0401422
• 作为产物：
  描述：

  (3S,8S,8aS)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-8-methoxy-6-methyl-hexahydro-indolizin-5-one 在 sodium hydroxide 、 sodium dihydrogenphosphate 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium chlorite 、 commercial bleach 、 四丁基氟化铵 、 叔丁基锂 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙腈 为溶剂， 反应 44.0h， 生成 (3S,6S,8S,8aS)-6-azido-8-methoxy-6-methyl-5-oxo-octahydroindolizine-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of 3₁₀-Helix-Inducing Constrained Analogues of l-Proline

  摘要：

  A bicyclic indolizidinone carboxylic acid and a tricyclic constrained analogue Of L-proline were synthesized and evaluated for their ability to induce helix formation as L-Ala tetrapeptides. Variable-temperature NMR, DMSO titration, CD spectra, and X-ray structure analyses, in conjunction with molecular modeling, confirmed the existence of 3(10)-helical motifs with di- and tetrapeptides Of L-Ala.

  DOI：

  10.1021/jo0401422

文献信息

• Synthesis of 3₁₀-Helix-Inducing Constrained Analogues of <scp>l</scp>-Proline
  作者：Stephen Hanessian、Gianluca Papeo、Kamal Fettis、Eric Therrien、Minh Tan Phan Viet

  DOI：10.1021/jo0401422

  日期：2004.7.1

  A bicyclic indolizidinone carboxylic acid and a tricyclic constrained analogue Of L-proline were synthesized and evaluated for their ability to induce helix formation as L-Ala tetrapeptides. Variable-temperature NMR, DMSO titration, CD spectra, and X-ray structure analyses, in conjunction with molecular modeling, confirmed the existence of 3(10)-helical motifs with di- and tetrapeptides Of L-Ala.