2-三甲基锡甲基苯甲酸甲酯 | 97729-12-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-三甲基锡甲基苯甲酸甲酯
• 中文别名: 2,3-二苯基喹啉
• 英文名称: methyl 2-[(trimethylsilyl)methyl]benzoate
• 英文别名: Methyl 2-((trimethylsilyl)methyl)benzoate；methyl 2-(trimethylsilylmethyl)benzoate
• CAS: 97729-12-9
• 化学式: C₁₂H₁₈O₂Si
• 分子量: 222.359
• InChiKey: PKYHEBNCHVLDEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.89
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2931900090

反应信息

• 作为反应物：
  描述：

  2-三甲基锡甲基苯甲酸甲酯 在 N-溴代丁二酰亚胺(NBS) 、 cesium fluoride 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 dimethyl bis-2,2'-(1,2-ethenediyl)benzoate
  参考文献：
  名称：

  Fluoride ion promoted reactions of .alpha.-halo silanes: synthesis of stilbenes, epoxides, cyclopropanes, benzazepines, and phthalidylisoquinolines

  摘要：

  Reaction of alpha-halo silanes 1 with CsF in DMF affords stilbenes 5. In the presence of added aldehydes, epoxides 6 are obtained, while with electron-deficient olefins the corresponding cyclopropanes 7 are formed. A similar reaction of 1a with iminium compounds 8 in HMPA leads to 2-phenyl-3-benzazepines 12, whereas 1b or 17 furnishes phthalidylisoquinolines 15.

  DOI：

  10.1021/jo00012a024
• 作为产物：
  描述：

  碘甲基三甲基硅烷 、 2-碘苯甲酸甲酯 在 1,1,3,3-四甲基脲 、 锌 、 1,1'-双(二苯基膦)二茂铁 、 chloro(1,5-cyclooctadiene)rhodium(I) dimer 作用下， 反应 30.0h， 以58%的产率得到2-三甲基锡甲基苯甲酸甲酯
  参考文献：
  名称：

  Synthesis of Functionalized Benzylsilanes from Arylzinc Compounds and (Iodomethyl)trimethylsilane by Means of a Novel Rh Catalysis

  摘要：

  [GRAPHICS]The catalytic activity of a Rh complex in cross-coupling between ArZnI and TMSCH2I was examined in which the Rh complex, generated in situ from [RhCl(1,5-cyclooctadiene)](2) and 1,1'-bis(diphenylphosphino)ferrocene, exhibited excellent catalytic activity for the production of various functionalized benzylsilanes in good yields. From P-31 NMR studies of various solutions containing several of the reaction components, confirmation of the rapid and quantitative transfer of aryl groups from ArZnI to the Rh complex to form arylrhodium species was ascertained. A catalytic cycle, commencing with the transmetalation, was thus proposed for the reaction.

  DOI：

  10.1021/jo0520994

文献信息

• A NEW FLUORIDE ANION-PROMOTED 1,4-CYCLOADDITION LEADING TO SYNTHESIS OF α-TETRALONES
  作者：Masahiro Aono、Yoshiyasu Terao、Kazuo Achiwa

  DOI：10.1246/cl.1985.339

  日期：1985.3.5

  Fluoride anion-promoted 1,4-cycloaddition of methyl o-trimethylsilylmethylbenzoate to conjugated olefins was found to give α-tetralones and uncyclized Michael adducts in moderate yields.

  研究发现，在氟阴离子的促进下，邻三甲硅基甲基苯甲酸甲酯与共轭烯烃发生 1,4-环加成反应，以中等产率生成了 α-四氢萘酮和未环化的迈克尔加合物。
• Kessar, Satinder V.; Singh, Paramjit; Venugopal, D., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 605 - 606
  作者：Kessar, Satinder V.、Singh, Paramjit、Venugopal, D.

  DOI：——

  日期：——
• An Efficient Approach to the Synthesis of 1,3-Diaryl-1,2,3,4-[4H]-tetrahydronaphthalene-2-carboxylic Acids
  作者：Jia-Ning Xiang、Ponnal Nambi、Eliot H. Ohlstein、John D. Elliott

  DOI：10.1016/s0968-0896(98)00022-4

  日期：1998.6

  A flexible approach to the synthesis of endothelin receptor antagonists of the 1,3-diaryl-1,2,3,4-[4H]-tetrahydronaphthalene-2-carboxylic acid class is described. (C) 1998 Elsevier Science Ltd. All rights reserved.
• AONO, MASAHIRO;TERAO, YOSHIYASU;ACHIWA, KAZUO, CHEM. LETT., 1985, N 3, 339-340
  作者：AONO, MASAHIRO、TERAO, YOSHIYASU、ACHIWA, KAZUO

  DOI：——

  日期：——
• Fluoride ion promoted reactions of .alpha.-halo silanes: synthesis of stilbenes, epoxides, cyclopropanes, benzazepines, and phthalidylisoquinolines
  作者：Satinder V. Kessar、Paramjit Singh、Nachhattar Pal Kaur、Usha Chawla、Kalpana Shukla、Punam Aggarwal、D. Venugopal

  DOI：10.1021/jo00012a024

  日期：1991.6

  Reaction of alpha-halo silanes 1 with CsF in DMF affords stilbenes 5. In the presence of added aldehydes, epoxides 6 are obtained, while with electron-deficient olefins the corresponding cyclopropanes 7 are formed. A similar reaction of 1a with iminium compounds 8 in HMPA leads to 2-phenyl-3-benzazepines 12, whereas 1b or 17 furnishes phthalidylisoquinolines 15.