Methyl 2-ethyl-5-oxopentanoate | 109704-76-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Methyl 2-ethyl-5-oxopentanoate
• CAS: 109704-76-9
• 化学式: C₈H₁₄O₃
• 分子量: 158.197
• InChiKey: HOBLSTAJUJDTNI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  11
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Methyl 2-ethyl-5-oxopentanoate 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 65.0h， 生成 methyl (3aR,4S,11bS)-3-benzyl-4-[(2S)-2-methoxycarbonylbutyl]-1,2,3a,4,5,7-hexahydropyrrolo[2,3-d]carbazole-6-carboxylate
  参考文献：
  名称：

  Syntheses of 20'-deoxyvinblastine, 20'-deoxyleurosidine, 20'-deoxyvincovaline, 20'-epi-20'-deoxyvincovaline, and 20'-deoxyvincristine and its 20'-epimer through racemic and enantioselectively generated intermediates. New syntheses of D/E-cis- and trans-.PSI.-vincadifformines and D/E-cis- and -trans-20-epi-.PSI.-vincadifformines

  摘要：

  DOI：

  10.1021/jo00275a029
• 作为产物：
  描述：

  3-乙基四氢-2H-吡喃-2-酮 在 硫酸 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 19.5h， 生成 Methyl 2-ethyl-5-oxopentanoate
  参考文献：
  名称：

  Syntheses of 20'-deoxyvinblastine, 20'-deoxyleurosidine, 20'-deoxyvincovaline, 20'-epi-20'-deoxyvincovaline, and 20'-deoxyvincristine and its 20'-epimer through racemic and enantioselectively generated intermediates. New syntheses of D/E-cis- and trans-.PSI.-vincadifformines and D/E-cis- and -trans-20-epi-.PSI.-vincadifformines

  摘要：

  DOI：

  10.1021/jo00275a029

文献信息

• Synthesis of vinblastine and vincristine type compounds
  申请人：University of Vermont & State Agricultural College

  公开号：US04841045A1

  公开（公告）日：1989-06-20

  A new process for the stereospecific synthesis of alkaloids of the vinblastine and vincristine type including the synthesis of vinblastine and vincristine as well novel alkaloids which are active as anti-tumor agents.

  一种新的立体选择性合成长春瑞碱和长春花碱类生物碱的工艺，包括合成长春瑞碱和长春花碱以及新型生物碱，这些生物碱具有抗肿瘤活性。
• 10.1039/d4sc02802c
  作者：Xie, Kejing、Shen, Zeyuan、Cheng, Peng、Dong, Haoxiang、Yu, Zhi-Xiang、Zu, Liansuo

  DOI：10.1039/d4sc02802c

  日期：——

  The Pictet–Spengler type condensation of tryptamine derivatives and aldehydes or ketones is a classic reaction, and has been previously applied to assemble indole-annulated 5-, 6- and 8-membered heterocyclic rings. In this work, we further expand the synthetic scope of this reaction to the 7-membered azepino[4,5-b]indole skeleton through the direct C–H functionalization of 2-alkyl tryptamines, in which

  色胺衍生物与醛或酮的 Pictet-Spengler 型缩合是一个经典反应，之前已被应用于组装吲哚环 5、6 和 8 元杂环。在这项工作中，我们通过2-烷基色胺的直接C-H官能化，进一步将该反应的合成范围扩展到7元氮杂[4,5- b ]吲哚骨架，其中未活化的亚甲基参与与醛形成7元环。通过将这种前所未有的成环过程与同一碳上的第二次 C-H 烯化相结合，实现了天然产物 ngouniensines 的简明全合成，证明了所开发的化学在简化逆合成断开方面的合成潜力。
• Synthesis of vinca alkaloids and related compounds. 64. Total syntheses of (.+-.)-pseudovincadifformine and (.+-.)-20-epipseudovincadifformine
  作者：Gyorgy Kalaus、Istvan Greiner、Maria Kajtar-Peredy、Janos Brlik、Lajos Szabo、Csaba Szantay

  DOI：10.1021/jo00074a039

  日期：1993.10

  Using our previously reported convergent synthetic strategy, secondary amine 6 and aldehyde 9 reacted to give tetracyclic esters 10 and 11, which readily led to pentacyclic lactams 14-16. Selective reduction of these products gave (+/-)-pseudovincadifformine (4), (+/-)-20-epipseudovincadifformine (5), and (+/-)-14-epipseudovincadifformine (20). Aldehyde 23 was also prepared and could be directly used for synthesizing (+/-)-20-epipseudovincadifformine (5). The introduction of the double bond into ring D of the pseudoaspidospermane skeleton was successfully achieved to obtain 21-oxopseudotabersonine (30).
• KUEHNE, MARTIN E.;BORNMANN, WILLIAM G., J. ORG. CHEM., 54,(1989) N4, C. 3407-3420
  作者：KUEHNE, MARTIN E.、BORNMANN, WILLIAM G.

  DOI：——

  日期：——
• KUEHNE, MARTIN
  作者：KUEHNE, MARTIN

  DOI：——

  日期：——