2-<(Trimethylsilyl)methyl>benzaldehyde | 81522-28-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-<(Trimethylsilyl)methyl>benzaldehyde
• 英文别名: o-<(trimethylsilyl)methyl>benzaldehyde；o-(trimethylsilyl)methyl benzaldehyde；2-(Trimethylsilylmethyl)benzaldehyde
• CAS: 81522-28-3
• 化学式: C₁₁H₁₆OSi
• 分子量: 192.333
• InChiKey: JLRRMHMDTHMAND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.92
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-<(Trimethylsilyl)methyl>benzaldehyde 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 2--3,3,4(S)-trimethyl-5(R)-phenyloxazolidinium triflate
  参考文献：
  名称：

  A new approach to asymmetric synthesis of polycycles on the basis of o-quinodimethane generation

  摘要：

  DOI：

  10.1021/ja00344a028
• 作为产物：
  描述：

  2-phenyl>-3,4,4-trimethyloxazolinium iodide 在 盐酸 、 sodium tetrahydroborate 、 三乙胺 作用下， 生成 2-<(Trimethylsilyl)methyl>benzaldehyde
  参考文献：
  名称：

  A new approach to asymmetric synthesis of polycycles on the basis of o-quinodimethane generation

  摘要：

  DOI：

  10.1021/ja00344a028

文献信息

• Silyl Migration in the Photochemical Reactions of 2-Trimethylsilylmethylphenyl Ketones
  作者：Masaichi Saito、Akitomo Saito、Yuko Ishikawa、Michikazu Yoshioka

  DOI：10.1021/ol050673s

  日期：2005.7.1

  [reaction: see text]. Irradiation of 2-trimethylsilylmethylphenyl ketones 1 gives benzocyclobutenols 2 and 5 together with siloxybenzocyclobutenes 4. Compound 4 arises from the novel photoinduced 1,5-silyl migration of 1. Irradiation of 1 in the presence of magnesium perchlorate gives the less hindered benzocyclobutenols 5 without the formation of 4. The mechanism of the photochemical reaction of 1

  [反应：请参见文字]。辐照2-三甲基甲硅烷基甲基苯基酮1可获得苯并环丁烯醇2和5以及甲硅烷氧基苯并环丁烯4。化合物4由1的新型光致1，5-甲硅烷基迁移产生。辐照1在高氯酸镁存在下产生的受阻较少的苯并环丁烯醇5没有讨论4的形成。讨论了1的光化学反应的机理。
• Photochemical reaction of ortho-formylbenzyltrialkylstannanes for the generation of α-oxy-o-quinodimethane
  作者：Hiroshi Sano、Daisuke Asanuma、Masanori Kosugi

  DOI：10.1039/a904872c

  日期：——

  Irradiation of o-formylbenzyltrialkylstannanes in benzene gives α-trialkylstannoxy-o-quinodimethanes which are trapped with dienophiles at room temperature to afford cycloadducts with high stereoselectivities, while the corresponding silane and germane gave a different type of o-quinodimethane and moderate stereoselectivities in cycloadditions.

  邻甲酰基苄基三烷基锡烷在苯中的辐照产生α-三烷基锡氧基-邻醌二甲烷，在室温下与亲双烯体捕获以提供具有高立体选择性的环加合物，而相应的硅烷和锗烷在环加成中给出不同类型的邻醌二甲烷和中等立体选择性。
• A Novel Method for the Conversion of the Alcohol to the Aldehyde via 1,5-Silicon Rearrangement
  作者：Gwang Mi Moon、Byeang Hyean Kim

  DOI：10.1080/00397919108019769

  日期：1991.4

  Abstract A conceptually novel method for the conversion of alcohols to aldehydes is reported. The 1,5 - silicon rearrangement is involved as the key element of the reaction.

  摘要 报道了一种概念上将醇转化为醛的新方法。1,5-硅重排是反应的关键元素。
• Intramolecular Reactivity of Arylcarbenes: Derivatives of o-Tolylcarbene
  作者：Wolfgang Kirmse、Wolfgang Konrad、Dirk Schnitzler

  DOI：10.1021/jo00093a014

  日期：1994.7

  Various CH(2)X groups have been attached to the ortho position of phenylcarbene. If 2'- or 3'-C-H bonds are present, as in 23 (X = Me), 71 (X = CMe(3)), and 58 (X = SiMe(3)), C-H insertion leading to five- or six-membered rings predominates in the gas phase and competes with intermolecular reactions in solution. The formation of benzocyclobutenes via insertion into 1'-C-H bonds is a very minor reaction path of 23 and 71. In contrast, 58 produces substantial amounts of the benzocyclobutene 59 by way of C-Si insertion, particularly in the gas phase. Insertion into the Si-Me bonds of 58 also occurs while the C-F bonds of 37 (X = CF3) and 50 (X = Fl are inert. In the gas phase, 37 and 50 give mainly benzocyclobutenes whereas intermolecular reactions prevail in solution. The effects of sensitization and of solvent polarity suggest that benzocyclobutenes arise from singlet arylcarbenes. The amount of carbene-carbene rearrangement decreases in the order 7 (X = H) > 37 (X = CF3) > 23 (X = Me); no rearrangement was observed with 50 (X = Fl, 58 (X = SiMe(3)), and 71 (X = CMe(3)).
• Kirmse, Wolfgang; Konrad, Wolfgang, Angewandte Chemie, 1990, vol. 102, # 6, p. 682 - 683
  作者：Kirmse, Wolfgang、Konrad, Wolfgang

  DOI：——

  日期：——