cuscutamine methyl ester | 82535-75-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: cuscutamine methyl ester
• 英文别名: (5S,11bR)-methyl 3-oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole-5-carboxylate；methyl (5S,11bR)-3-oxo-1,2,5,6,11,11b-hexahydroindolizino[8,7-b]indole-5-carboxylate
• CAS: 82535-75-9
• 化学式: C₁₆H₁₆N₂O₃
• 分子量: 284.315
• InChiKey: QVCCUGYLVYNCBO-OLZOCXBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  62.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cuscutamine methyl ester 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 叔丁醇 为溶剂， 反应 48.0h， 以11%的产率得到trichotomine dimethyl ester
  参考文献：
  名称：

  草木松中四种2,3,5,6,11,11b-Hexahydro-3-oxo-1H-indolizino[8,7-b]indole-5-羧酸的分离及其衍生物性质

  摘要：

  四种 2,3,5,6,11,11b-hexahydro-3-oxo-1H-indolizino[8,7-b]indole-5-羧酸，trichotomine 的合理前体，被分离为来自 Clerodendron trichotomum 的甲酯Thunb 和根据光谱和化学证据阐明的结构。上述植物中两对 C-11b 差向异构体的存在得到了在 C-11b 上具有取代基的化合物的甲醇盐催化平衡的支持。蓝色颜料由分离的化合物形成。

  DOI：

  10.1246/bcsj.62.880
• 作为产物：
  描述：

  (5S,11bS)-3-Oxo-2,3,5,6,11,11b-hexahydro-1H-indolizino[8,7-b]indole-5-carboxylic acid methyl ester 生成 cuscutamine methyl ester
  参考文献：
  名称：

  IRIKAWA, HAJIME;TOYODA, YASUHIRO;KUMAGAI, HIROAKI;OKUMURA, YASUAKI, BULL. CHEM. SOC. JAP., 62,(1989) N, C. 880-887

  摘要：

  DOI：

文献信息

• Synthesis of Heterocycles through a Ruthenium-Catalyzed Tandem Ring-Closing Metathesis/Isomerization/N-Acyliminium Cyclization Sequence
  作者：Erhad Ascic、Jakob F. Jensen、Thomas E. Nielsen

  DOI：10.1002/anie.201100417

  日期：2011.5.23

  Tandem bicycle: In the title reaction double bonds created during ring‐closing metathesis isomerize to generate reactive iminium intermediates that undergo intramolecular cyclization reactions with tethered heteroatom and carbon nucleophiles. In this way, a series of biologically interesting heterocyclic compounds can be made, including a known precursor for the total synthesis of the antiparasitic

  串联自行车：在标题反应中，在闭环易位过程中产生的双键异构化，生成反应性亚胺基中间体，这些中间体与束缚的杂原子和碳亲核试剂进行分子内环化反应。以此方式，可以制备一系列生物学上令人感兴趣的杂环化合物，包括用于抗寄生虫天然产物毒品的全合成的已知前体。
• ISOLATION OF FOUR INDOLIZINO[8,7-<i>b</i>]INDOLE-5-CARBOXYLIC ACIDS FROM CLERODENDRON TRICHOTOMUM THUNB
  作者：Yasuhiro Toyoda、Hiroaki Kumagai、Hajime Irikawa、Yasuaki Okumura

  DOI：10.1246/cl.1982.903

  日期：1982.6.5

  Four indolizino[8,7-b]indole-5-carboxylic acids were isolated as the methyl esters from Clerodendron trichotomum Thunb, and the structures elucidated on the basis of their spectral and chemical evidences.

  从三棱木（Clerodendron trichotomum Thunb）中分离出了四种吲哚并吲哚-5-羧酸的甲基酯，并根据它们的光谱和化学证据阐明了其结构。
• Autoxidation of Indolo[3,2,1-<i>de</i>][1,5]naphthyridines
  作者：Hajime Irikawa、Yasuaki Okumura

  DOI：10.1246/bcsj.60.3797

  日期：1987.10

  The yellow keto lactam and the blue dimeric pigment were formed by the autoxidation of indolo[3,2,1-de][1,5]naphthyridines.

  黄色酮内酰胺和蓝色二聚体颜料是由吲哚并[3,2,1-de][1,5]萘啶的自氧化形成的。
• Pd(II)-Catalyzed <i>meta</i>-C–H Olefination, Arylation, and Acetoxylation of Indolines Using a U-Shaped Template
  作者：Guoqiang Yang、Petra Lindovska、Dajian Zhu、Justin Kim、Peng Wang、Ri-Yuan Tang、Mohammad Movassaghi、Jin-Quan Yu

  DOI：10.1021/ja505737x

  日期：2014.7.30

  meta-C-H olefination, arylation, and acetoxylation of indolines have been developed using nitrile-containing templates. The combination of a monoprotected amino acid ligand and the nitrile template attached at the indolinyl nitrogen via a sulfonamide linkage is crucial for the meta-selective C-H fiunctionalization of electron-rich indolines that are otherwise highly reactive toward electrophilic palladation at the para-positions. A wide range of synthetically important and advanced indoline analogues are selectively functionalized at the meta-positions.
• 2,5-Dimethoxy-2,5-Dihydrofuran as a Synthetic Equivalent of 3-Formyl Alkylpropionate in Pictet-Spengler Type Reactions
  作者：Fontaine, Helene、Baussanne, Isabelle、Royer, Jacques

  DOI：10.1080/00397919708004157

  日期：1997.8

  2,5-dimethoxy-2,5-dihydrofuran has been used as a synthetic equivalent of 3-formyl propionate in the Pictet-Spengler type reaction of 2-aryl ethylamines to provide the corresponding arylindolizidinones in moderate yields.