6,11-dihydrochromeno[4,3'-b]indole | 6722-06-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 6,11-dihydrochromeno[4,3'-b]indole
• 英文别名: 6,11-dihydrochromeno[4,3-b]indole；6,11-dihydro-chromeno[4,3-b]indole；6,11-Dihydro-<1>benzopyrano-<4,3-b>indol；6,11-Dihydro<1>benzopyrano<4,3-b>indol；Chromeno<4,3-b>-<4,5>indol；6,11-Dihydro[1]benzopyrano[4,3-b]indole
• CAS: 6722-06-1
• 化学式: C₁₅H₁₁NO
• 分子量: 221.258
• InChiKey: REPMWBJJSQQFMS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  25
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6,11-dihydrochromeno[4,3'-b]indole 、 2-(bromomethyl)-3-((tert-butyldimethylsilyl)oxy)-4H-pyran-4-one 在 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-1-((R)-2-(3,5-di(naphthalen-2-yl)phenyl)pyrrolidin-1-yl)-3,3-dimethyl-1-oxobutan-2-yl)thiourea 、 苯甲酸 作用下， 以 甲基叔丁基醚 为溶剂， 反应 72.0h， 以86%的产率得到2-[[(6aS)-6H-chromeno[4,3-b]indol-6a-yl]methyl]-3-hydroxypyran-4-one
  参考文献：
  名称：

  Thiourea-Catalyzed Enantioselective Addition of Indoles to Pyrones: Alkaloid Cores with Quaternary Carbons

  摘要：

  We report the development of a catalytic method for the enantioselective addition of indoles to pyrone-derived electrophiles. Arylpyrrolidino-derived thioureas catalyze the addition with high stereoselectivity in the presence of catalytic quantities of an achiral Bronsted acid. The indole-pyrone adducts feature a quaternary stereocenter and represent an unusual class of indolines bearing structural resemblance to the hybrid natural product pleiocarpamine.

  DOI：

  10.1021/ja508523g
• 作为产物：
  描述：

  chroman-4-one phenylhydrazone 在 盐酸 作用下， 以 溶剂黄146 为溶剂， 生成 6,11-dihydrochromeno[4,3'-b]indole
  参考文献：
  名称：

  致癌的氮化合物。第LII部分。[1] Benzothiopyrano- [4,3- b ]吲哚，[1]苯并吡喃基[4,3- b ]吲哚和相关的假azulenes

  摘要：

  [1] Benzothiopyrano [4,3- b ]吲哚及其几种衍生物已通过相应的6,11-二氢化合物的多种脱氢方法合成。研究了这些含硫杂环的结构和性质，并与它们的氧类似物进行了比较。

  DOI：

  10.1039/j39660001787

文献信息

• Mild, efficient Fischer indole synthesis using 2,4,6-trichloro-1,3,5-triazine (TCT)
  作者：Eranna Siddalingamurthy、Kittappa M. Mahadevan、Jagadeesh N. Masagalli、Hosanagara N. Harishkumar

  DOI：10.1016/j.tetlet.2013.07.157

  日期：2013.10

  Mild and efficient protocol for the Fischer indole synthesis using TCT has been described. TCT serves as a mild and inexpensive catalyst. Under these conditions several functional groups such as ester, cyano, sulfone, amides, and ethers are tolerated. By this method, many functionalized analytically pure indoles were prepared easily without the need of purification. (C) 2013 Elsevier Ltd. All rights reserved.
• Sharkova,N.M. et al., Journal of general chemistry of the USSR, 1962, vol. 32, p. 3572 - 3576
  作者：Sharkova,N.M. et al.

  DOI：——

  日期：——
• Thiourea-Catalyzed Enantioselective Addition of Indoles to Pyrones: Alkaloid Cores with Quaternary Carbons
  作者：Charles S. Yeung、Robert E. Ziegler、John A. Porco、Eric N. Jacobsen

  DOI：10.1021/ja508523g

  日期：2014.10.1

  We report the development of a catalytic method for the enantioselective addition of indoles to pyrone-derived electrophiles. Arylpyrrolidino-derived thioureas catalyze the addition with high stereoselectivity in the presence of catalytic quantities of an achiral Bronsted acid. The indole-pyrone adducts feature a quaternary stereocenter and represent an unusual class of indolines bearing structural resemblance to the hybrid natural product pleiocarpamine.
• Carcinogenic nitrogen compounds. Part LII. [1]Benzothiopyrano-[4,3-b]indoles, [1]benzopyrano[4,3-b]indoles, and related pseudo-azulenes
  作者：N. P. Buu-Hoï、A. Martani、A. Croisy、P. Jacquignon、F. Périn

  DOI：10.1039/j39660001787

  日期：——

  [1]Benzothiopyrano[4,3-b]indole and several of its derivatives have been synthesised by various methods of dehydrogenation of the corresponding 6,11-dihydro-compounds. The structure and properties of these sulphur-containing heterocycles are investigated and compared with those of their oxygen analogues.

  [1] Benzothiopyrano [4,3- b ]吲哚及其几种衍生物已通过相应的6,11-二氢化合物的多种脱氢方法合成。研究了这些含硫杂环的结构和性质，并与它们的氧类似物进行了比较。