4-((三甲基甲硅烷基)甲基)苯甲酸 | 17095-21-5

• 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: 4-((三甲基甲硅烷基)甲基)苯甲酸
• 英文名称: 4-(Trimethylsilyl-methyl)-benzoesaeure
• 英文别名: 4--benzoesaeure；4-((Trimethylsilyl)methyl)benzoic acid；4-(trimethylsilylmethyl)benzoic acid
• CAS: 17095-21-5
• 化学式: C₁₁H₁₆O₂Si
• 分子量: 208.332
• InChiKey: IROWHUDNITYWNJ-UHFFFAOYSA-N

物化性质

• 熔点：
  178 °C
• 沸点：
  293.4±23.0 °C(Predicted)
• 密度：
  1.023±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 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：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-((三甲基甲硅烷基)甲基)苯甲酸 在 吡啶 、 lithium aluminium tetrahydride 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙醚 、 氘代乙腈 为溶剂， 反应 0.5h， 生成 p-xylylene
  参考文献：
  名称：

  Room Temperature Observation of p-Xylylenes by ¹H NMR and Evidence for Diradical Intermediates in Their Oligomerization

  摘要：

  p-Quinodimethanes (p-QDMs) are reactive molecules that have been invoked as transient intermediates in a number of reactions. Dilute solutions of benzene-based p-QDMs, p-xylylene (1), a-methyl-p-xylylene (10), and 2,5-dimethyl-p-xylylene (11) can be prepared by fluoride-induced elimination of trimethylsilyl acetate from the appropriate precursor. It has been found that these solutions are stable enough to allow these reactive p-QDMs to be observed by H-1 NMR spectroscopy at room temperature. For the first time, the 13 C NMR spectrum of p-QDM 1 was observed. After several hours at room temperature, these p-QDMs form dimers, trimers, and insoluble oligomers. Formation of trimers provides evidence that p-QDMs 1, 10, and 11 dimerize by a stepwise mechanism involving dimeric diradicals as intermediates.

  DOI：

  10.1021/jo0516279
• 作为产物：
  描述：

  (4-氯苯基)甲基三甲基硅烷 在 lithium 作用下， 生成 4-((三甲基甲硅烷基)甲基)苯甲酸
  参考文献：
  名称：

  有机硅化合物。第八部分 （三甲基甲硅烷基甲基）苯甲酸

  摘要：

  DOI：

  10.1039/jr9540000939

文献信息

• Discriminating non-ylidic carbon-sulfur bond cleavages of sulfonium ylides for alkylation and arylation reactions
  作者：Jing Fang、Ting Li、Xiang Ma、Jiuchang Sun、Lei Cai、Qi Chen、Zhiwen Liao、Lingkui Meng、Jing Zeng、Qian Wan

  DOI：10.1016/j.cclet.2021.06.069

  日期：2022.1

  The disparate reaction pattern allowed the separate activation of non-ylidic S-alkyl and S-aryl bond. Under acidic conditions, sulfonium ylides serve as alkyl cation precursors which facilitate the alkylations. While under alkaline conditions, cleavage of non-ylidic S-aryl bond produces O-arylated compounds efficiently. The robustness of the protocols were established by the excellent compatibility of

  描述了一种在无过渡金属条件下参与烷基化和芳基化的锍叶立德。不同的反应模式允许单独激活非叶立基S-烷基和S-芳基键。在酸性条件下，锍叶立德用作促进烷基化的烷基阳离子前体。而在碱性条件下，非叶立基 S-芳基键的断裂可有效地产生O-芳基化化合物。协议的稳健性是由包括碳水化合物在内的各种底物的出色兼容性建立的。
• Substituent effects of mono-, bis-, and tris(trimethylsilyl)methyl groups; determination of σ− and σ+-constants
  作者：M.A. Cook、C. Eaborn、D.R.M. Walton

  DOI：10.1016/s0022-328x(00)80267-3

  日期：1970.9

  2H in 50% aqueous ethanol at 25° have been measured and used to give the following σ-constants for the p-[(Me3Si)xCH(3−x)] groups: x = 1, −0.29; x = 2, −0.33; x = 3, −0.27. The rates of solvolysis of the tertiary chlorides p-[(Me3Si)xCH(3−x)]C6H4CMe2Cl in aqueous acetone have also been measured and used to give the following σ+-constants: x = 1, −0.54; x = 2, −0.62; x = 3, −0.52. The results are consistent

  测量了酸p -[（Me 3 Si）x CH （3- x） ] C 6 H 4 CO 2 H在25％的50％乙醇水溶液中的表观解离常数，并用于给出以下σ常数对于p -[（Me 3 Si）x CH （3- x） ]基团：x = 1，-0.29; x = 2，-0.33；x＝ 3，-0.27。叔氯化物p -[（Me 3 Si）x CH （3- x）还测量了在丙酮水溶液中的C 6 H 4 CMe 2 Cl，并将其用于给出以下σ +常数：x = 1，-0.54; x = 2，-0.62；x = 3，-0.52。结果是具有大量电子hyperconjugative释放从ME存在一致3 SiC键。
• The unusually slow hydrolysis rate of silyl methyl ketals in benzoquinone systems. The question of siloxy stabilization of an adjacent positive charge and stereoelectronic effects on ketal hydrolysis
  作者：Alan J. Stern、John S. Swenton

  DOI：10.1021/jo00273a033

  日期：1989.6
• STERN, ALAN J.;SWENTON, JOHN S., J. ORG. CHEM., 54,(1989) N2, C. 2953-2958
  作者：STERN, ALAN J.、SWENTON, JOHN S.

  DOI：——

  日期：——
• Room Temperature Observation of <i>p-</i>Xylylenes by ¹H NMR and Evidence for Diradical Intermediates in Their Oligomerization
  作者：Walter S. Trahanovsky、Steven P. Lorimor

  DOI：10.1021/jo0516279

  日期：2006.3.1

  p-Quinodimethanes (p-QDMs) are reactive molecules that have been invoked as transient intermediates in a number of reactions. Dilute solutions of benzene-based p-QDMs, p-xylylene (1), a-methyl-p-xylylene (10), and 2,5-dimethyl-p-xylylene (11) can be prepared by fluoride-induced elimination of trimethylsilyl acetate from the appropriate precursor. It has been found that these solutions are stable enough to allow these reactive p-QDMs to be observed by H-1 NMR spectroscopy at room temperature. For the first time, the 13 C NMR spectrum of p-QDM 1 was observed. After several hours at room temperature, these p-QDMs form dimers, trimers, and insoluble oligomers. Formation of trimers provides evidence that p-QDMs 1, 10, and 11 dimerize by a stepwise mechanism involving dimeric diradicals as intermediates.