镁,1H-吲哚-1-基碘- | 13884-15-6

• 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
• 中文名称: 镁,1H-吲哚-1-基碘-
• 英文名称: (Indol-1-yl)magnesium iodide
• 英文别名: 1-Indolyl magnesium iodide；1-indolylmagnesium iodide；indolylmagnesium iodide；Indolylmagnesiumiodid；magnesium;4H-indol-4-ide;iodide
• CAS: 13884-15-6
• 化学式: C₈H₆N*I*Mg
• 分子量: 267.352
• InChiKey: WUOHHBBDIXOSSD-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.58
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,6-二氯哒嗪 、 镁,1H-吲哚-1-基碘- 以 乙醚 为溶剂， 以37%的产率得到3-(6-氯-3-哒嗪)-1H-吲哚
  参考文献：
  名称：

  Reinvestigation and extension of the aluminum chloride induced reactions of resorcinol and hydroquinone with 3,6-dichloropyridazine

  摘要：

  DOI：

  10.1021/jo00306a026
• 作为产物：
  描述：

  吲哚 在 碘 、 magnesium 、 碘甲烷 作用下， 以 乙醚 为溶剂， 反应 0.5h， 生成 镁,1H-吲哚-1-基碘-
  参考文献：
  名称：

  离子液体中环境吲哚离子的烷基化

  摘要：

  Alkylation of the ambident indole anion in ionic liquids has been investigated. The reaction rate is greater in ionic liquids than in organic solvents. The polarity of certain ionic liquids has been determined to be located between methanol and acetonitrile.

  DOI：

  10.1007/s10593-008-0072-y

文献信息

• Application of 2-Substituted Ethyl Isothiocyanates and 2-Aminothiols in the Synthesis of the Analogs of Indole Phytoalexin Camalexin
  作者：Milan Dzurilla、Martin Ružinský、Peter Kutschy、Jalpa P. Tewari、Vladimír Kováčik

  DOI：10.1135/cccc19991448

  日期：——

  Treatment of (indol-1-yl)magnesium bromide or iodide with 2-bromoethyl isothiocyanate afforded 1-(4,5-dihydrothiazol-2-yl)indole (6). Analogous reaction with 2,2-dimethoxyethyl isothiocyanate led to corresponding 1-thiocarbamoylindole derivative (7), which was cyclized to 1-(5-methoxy-4,5-dihydrothiazol-2-yl)indole (8) by treatment with boron trifluoride etherate. New analogs of camalexin, namely 4',5'-dihydrocamalexin (12) and benzocamalexin (14) were prepared by cyclocondensation reaction of 1-(tert-butoxycarbonyl)indole-3-carbaldehyde with cysteamine and 2-aminobenzenethiol. Antifungal activity of the prepared compounds was studied, using the fungi Alternaria brassicae and Alternaria brassicicola.

  使用2-溴乙基异硫氰酸酯处理吲哚-1-基溴化镁或碘化镁，得到1-(4,5-二氢噻唑-2-基)吲哚（6）。类似的反应，使用2,2-二甲氧基乙基异硫氰酸酯，得到相应的1-硫代氨基甲酰吲哚衍生物（7），用氟化硼乙醚处理，环化成1-(5-甲氧基-4,5-二氢噻唑-2-基)吲哚（8）。通过1-(叔丁氧基羰基)吲哚-3-甲醛与半胱胺和2-氨基苯硫醇的环缩合反应，制备了卡玛列辛的新类似物，即4',5'-二氢卡玛列辛（12）和对苯卡玛列辛（14）。研究了所制备化合物对真菌Alternaria brassicae和Alternaria brassicicola的抑菌活性。
• Facile cycloaddition of 2-phenylsulfonyl 1,3-dienes to indoles
  作者：Jan-E. Bäckvall、Niklas A. Plobeck、Seppo K. Juntunen

  DOI：10.1016/s0040-4039(01)80458-5

  日期：1989.1

  2-Phenylsulfonyl 1,3-dienes react rapidly with the magnesium salt of indoles to give 3-(phenylsulfonyl)-1,4,4a,9a-tetrahydrocarbazoles via a formal [4+2] cycloaddition.

  2-苯基磺酰基1，3-二烯与吲哚的镁盐快速反应，通过正式的[4 + 2]环加成反应生成3-（苯基磺酰基）-1,4,4a，9a-四氢咔唑。
• Laatsch, Hartmut; Thomson, Ronald H.; Cox, Philip J., Journal of the Chemical Society. Perkin transactions II, 1984, # 8, p. 1331 - 1340
  作者：Laatsch, Hartmut、Thomson, Ronald H.、Cox, Philip J.

  DOI：——

  日期：——
• New synthesis of the 6H-pyrido[4,3-b]carbazoles ellipticine and olivacine via cycloaddition of 2-phenylsulfonyl 1,3-dienes to indoles
  作者：Jan E. Baeckvall、Niklas A. Plobeck

  DOI：10.1021/jo00302a013

  日期：1990.7
• A new convergent route to 1-substituted ellipticines
  作者：F. Marsais、P. Pineau、F. Nivolliers、M. Mallet、A. Turck、A. Godard、G. Queguiner

  DOI：10.1021/jo00028a032

  日期：1992.1

  1-(2-Fluoro-4-pyridyl)ethanone was synthesized from 2-fluoropyridine and was ortho-lithiated after activation as the propylene glycol ketal. The resulting 3-lithio derivative was trapped by various electrophiles but reacted in low yield with N-protected 3-indolecarbaldehyde. Model compounds 1-[[[2-(diethylamino)ethyl]amino]-3-pyridyl]ethanol and -ethanone were prepared and selectively condensed with indole. 1-[[[2-(Diethylamino)-ethyl]amino]-3-pyridyl]ethanol and -ethanone bearing a ketal-protected acetyl moiety at the C-4 position have been obtained in high yields starting from the propylene glycol ketal of 1-(2-fluoro-4-pyridyl)ethanone. These reagents could not be condensed with indole either due to side reactions between the C-3 and C-4 functions or to steric hindrance. 1-(2-Substituted-4-bromo-3-pyridyl)ethanols were synthesized via a metalation/halogen-dance strategy starting from 2-fluoropyridine. 1-(2,4-Dihalo-3-pyridyl)-1-chloroethane could be prepared and condensed with 1-indolylmagnesium iodide, which allowed the construction of the expected 3-[1-(3-pyridyl)ethyl]indole skeleton. Functionalization of the pyridine C-4 bromo position was achieved by a vinylstannane cross-coupling reaction using a palladium(0) catalyst. Acidic treatment of the resulting 4-(1-ethoxyethenyl)pyridine led to 1-fluoroellipticine. The whole sequence requires six steps from indole and 2-fluoropyridine and allows an attractive overall yield.