7-(tributylstannyl)-2,3-dihydroindole-1-carboxylic acid tert-butyl ester

• 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: 7-(tributylstannyl)-2,3-dihydroindole-1-carboxylic acid tert-butyl ester
• 英文别名: 1-(tert-butoxycarbonyl)-7-tributylstannylindoline
• 化学式: C₂₅H₄₃NO₂Sn
• 分子量: 508.332
• InChiKey: ZTXGMVRKYIHVIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.04
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-(tributylstannyl)-2,3-dihydroindole-1-carboxylic acid tert-butyl ester 在 盐酸 、 palladium diacetate 、 三乙胺 、 三(邻甲基苯基)磷 、 silver(l) oxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 50.0h， 生成 去氢石蒜碱酮
  参考文献：
  名称：

  A Synthesis of Pyrrolophenanthridone Alkaloids via Consecutive Directed Lithiation and Palladium-catalyzed Cross-coupling Reactions

  摘要：

  A short and convergent synthesis of pyrrolophenanthridone alkaloids, such as anhydrolycorin-7-one, oxoassoanine, hippadine, and pratosine, was developed by using directed lithiation and palladium-catalyzed cross-coupling as key reactions. Anhydrolycorin-7-one was converted to an antitumor alkaloid, kalbretorine, via directed lithiation and hydroxylation reactions.

  DOI：

  10.3987/com-94-6777

文献信息

• Indole Diterpene Synthetic Studies:  Development of a Second-Generation Synthetic Strategy for (+)-Nodulisporic Acids A and B
  作者：Amos B. Smith、László Kürti、Akin H. Davulcu、Young Shin Cho、Kazuyuki Ohmoto

  DOI：10.1021/jo062423a

  日期：2007.6.1

  A second-generation strategy for construction of (+)-nodulisporic acids A and B based on the development of a new, effective modular indole synthesis exploiting a sequential Stille cross-coupling/Buchwald−Hartwig union/cyclization tactic is disclosed. This strategy evolved due to the considerable acid instability of the C(24) hydroxyl group observed in several advanced intermediates during our first-generation

  公开了基于开发一种新的，有效的模块化吲哚合成的第二代构建（+）-去甲孢子酸A和B的策略，该合成利用顺序Stille交叉偶联/ Buchwald-Hartwig联合/环化策略。由于在我们的第一代方法中的几个高级中间体中观察到的C（24）羟基相当酸不稳定，因此该策略得以发展。
• An <i>o</i>-Iminothioquinone:  Its Cycloaddition To Produce an Indologlycoside and Its Self-Dimerization To Form a Dithio-Diazocycloctane, the Structure Assignment of Which Is Based on the DFT Prediction of Its IR Spectrum
  作者：Vinh Diep、J. J. Dannenberg、Richard W. Franck

  DOI：10.1021/jo034800e

  日期：2003.10.1

  An unusual heterodiene, an indolothiono quinone, undergoes cycloaddition with a glycal to form an indole-N-glycoside. A novel dimer of the indolothionoquinone is assigned its structure on the basis of a match between its predicted and observed IR spectrum.
• A Synthesis of Pyrrolophenanthridone Alkaloids via Consecutive Directed Lithiation and Palladium-catalyzed Cross-coupling Reactions
  作者：Masatomo Iwao、Hirokazu Takehara、Shigeru Obata、Mitsuaki Watanabe

  DOI：10.3987/com-94-6777

  日期：——

  A short and convergent synthesis of pyrrolophenanthridone alkaloids, such as anhydrolycorin-7-one, oxoassoanine, hippadine, and pratosine, was developed by using directed lithiation and palladium-catalyzed cross-coupling as key reactions. Anhydrolycorin-7-one was converted to an antitumor alkaloid, kalbretorine, via directed lithiation and hydroxylation reactions.