9,10-Didehydro-6-methylergolin | 51921-11-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 9,10-Didehydro-6-methylergolin
• 英文别名: DL-Descarboxylysergsaeure；7-methyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinoline；7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline
• CAS: 51921-11-0
• 化学式: C₁₅H₁₆N₂
• 分子量: 224.305
• InChiKey: AHFZNJIKXMBLTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  19
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  7-Methyl-4-(toluene-4-sulfonyl)-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinoline 在 magnesium 作用下， 以 甲醇 为溶剂， 以98%的产率得到9,10-Didehydro-6-methylergolin
  参考文献：
  名称：

  通过闭环易位新进入麦角生物碱

  摘要：

  已开发出一种新颖的麦角生物碱。它具有Heck反应，然后捕获氢化物以生成关键的三环中间体12和闭环易位反应，从而生成四环麦角灵环系统3。

  DOI：

  10.1016/s0040-4039(01)00002-8

文献信息

• Arene Trifunctionalization with Highly Fused Ring Systems through a Domino Aryne Nucleophilic and Diels–Alder Cascade
  作者：Jia He、Zizi Jia、Hongcheng Tan、Xiaohua Luo、Dachuan Qiu、Jiarong Shi、Hai Xu、Yang Li

  DOI：10.1002/anie.201911730

  日期：2019.12.16

  A convenient and efficient domino aryne process was developed under transition-metal-free conditions to generate a range of tetra- and pentacyclic ring systems. This transformation was realized via a 1,2-benzdiyne through a nucleophilic and Diels-Alder reaction cascade using styrene as the diene moiety. Three new chemical bonds, namely one C-N and two C-C bonds, and two benzofused rings could be constructed

  在无过渡金属的条件下，开发了一种方便有效的多米诺烷工艺，以生成一系列四环和五环体系。该转化是通过1，2-苯并二炔通过使用苯乙烯作为二烯部分的亲核和Diels-Alder反应级联实现的。可以同时构建三个新的化学键，即一个CN和两个CC键，以及两个苯并稠合环，这是通过在1,2-芳烃和2,3-芳烃阶段进行独特的化学选择性控制而实现的。此外，对多米诺骨牌烷前体和控制非对映选择性进行了深入研究。
• [EN] COMPOUNDS FOR THE TREATMENT OF NEURODEGENERATIVE AND METABOLIC DISORDERS<br/>[FR] COMPOSÉS POUR LE TRAITEMENT DE TROUBLES NEURODÉGÉNÉRATIFS ET MÉTABOLIQUES
  申请人：SCRIPPS RESEARCH INST

  公开号：WO2020232255A1

  公开（公告）日：2020-11-19

  Compounds described herein may be used for the treatment of neurodegenerative diseases linked to protein misfolding, including prion diseases, Alzheimers' disease, Parkinson's disease (PD) and amyotrophic lateral sclerosis (ALS), and also other neurodegenerative, degenerative, metabolic and ischemic conditions. Indeed, NAD metabolism impairment is also a critical feature in brain ischemia/reperfusion injury, Wallerian degeneration, kidney failure, multiple sclerosis, aging, and metabolic disorders such as diabetes mellitus. Therapies that elevate or stabilize NAD levels may thus have broad potential for treating many severely debilitating neurological and metabolic conditions. Evidence is provided herein with compounds from 8 lead series for NAD restoring properties and for therapeutic efficacy in cellular and/or animal models of prion disease, PD and ALS.
• Novel entry to the Ergot alkaloids via ring closing metathesis
  作者：Katherine L Lee、Jane Betty Goh、Stephen F Martin

  DOI：10.1016/s0040-4039(01)00002-8

  日期：2001.2

  A novel entry the Ergot alkaloids has been developed. It features a Heck reaction followed by hydride capture to generate the key tricyclic intermediate 12 and a ring closing metathesis reaction to give the tetracyclic ergoline ring system 3.

  已开发出一种新颖的麦角生物碱。它具有Heck反应，然后捕获氢化物以生成关键的三环中间体12和闭环易位反应，从而生成四环麦角灵环系统3。