6-oxo-2,3,6,7,7a,8-hexahydro-1H,4H-3a-aza-s-indacene-8a-carboxylic acid methyl ester | 355393-40-7

• 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: 6-oxo-2,3,6,7,7a,8-hexahydro-1H,4H-3a-aza-s-indacene-8a-carboxylic acid methyl ester
• 英文别名: methyl (8aR,9aR)-7-oxo-2,3,5,8,8a,9-hexahydro-1H-cyclopenta[f]indolizine-9a-carboxylate
• CAS: 355393-40-7
• 化学式: C₁₃H₁₇NO₃
• 分子量: 235.283
• InChiKey: VNTGQBRZCFTVHR-TVQRCGJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-oxo-2,3,6,7,7a,8-hexahydro-1H,4H-3a-aza-s-indacene-8a-carboxylic acid methyl ester 在 silica gel 作用下， 以 甲醇 、 水 为溶剂， 反应 23.0h， 生成 11,13-diaza-4,13-dimethyltetracyclo[5.5.2.0^1,5.0^7,11]tetradecane-3,14-dione
  参考文献：
  名称：

  A new pathway to chiral tetracyclic indolidines via Pauson–Khand reaction

  摘要：

  Reaction of enynes 1 and 3 with Co-2(CO)(8) in the presence of DMSO, NMO or TMANO as promoters produced tricyclic indolidine derivatives 5 and 7 stereoselectively in moderate to excellent yield. The stereochemistry at the C-7 position of the indolidines 5 and 7 was confirmed by their conversion into the bridged azacycles 10 and 13. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00645-1
• 作为产物：
  描述：

  methyl L-2-allylprolinate hydrochloride 在 碳酸氢钠 、 lithium iodide 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 28.0h， 生成 6-oxo-2,3,6,7,7a,8-hexahydro-1H,4H-3a-aza-s-indacene-8a-carboxylic acid methyl ester
  参考文献：
  名称：

  A new pathway to chiral tetracyclic indolidines via Pauson–Khand reaction

  摘要：

  Reaction of enynes 1 and 3 with Co-2(CO)(8) in the presence of DMSO, NMO or TMANO as promoters produced tricyclic indolidine derivatives 5 and 7 stereoselectively in moderate to excellent yield. The stereochemistry at the C-7 position of the indolidines 5 and 7 was confirmed by their conversion into the bridged azacycles 10 and 13. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00645-1

文献信息

• An efficient construction of bridged chiral tetracyclic indolidines, a core structure of asperparaline, via stereocontrolled catalytic Pauson–Khand reaction
  作者：Shinji Tanimori、Tatsuya Sunami、Kouji Fukubayashi、Mitsunori Kirihata

  DOI：10.1016/j.tet.2004.12.057

  日期：2005.2

  A reaction of chiral enyne 22 derived from l-proline with a catalytic amount of cobalt (0) octacarbonyl in the presence of N-methylmorphorine N-oxide gave tricyclic enone 24 in 54% yield (73% based on consumed starting material). Treatment of enone 11 with aqueous methylamine followed by silica gel afforded bridged tetracyclic indolidine 1, a common structural motif of natural metabolites, an asperparaline

  在N-甲基吗啡啉N-氧化物存在下，衍生自1-脯氨酸的手性烯炔22与催化量的钴（0）八羰基化合物的反应以54％的收率得到三环烯酮24（基于消耗的原料为73％）。用甲基胺水溶液和硅胶处理烯酮11，得到桥连的四环吲哚啶1，它是天然代谢产物的常见结构基序，天冬酰胺系列化合物以及潜在的中间体，用于合成麻痹性生物碱天冬酰胺C（4）。 70％的产率。