N-<3-(trimethylsilyl)propyl>phthalimide | 20983-48-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: N-<3-(trimethylsilyl)propyl>phthalimide
• 英文别名: N-[3-(trimethylsilyl)propyl]phthalimide；N-(3-trimethylsilanyl-propyl)-phthalimide；2-[3-(trimethylsilyl)propyl]-1H-isoindole-1,3(2H)-dione；N-(3-Trimethylsilyl-propyl)-phthalimid；2-(3-Trimethylsilylpropyl)isoindole-1,3-dione
• CAS: 20983-48-6
• 化学式: C₁₄H₁₉NO₂Si
• 分子量: 261.396
• InChiKey: QJQQNNSHROXTQJ-UHFFFAOYSA-N

物化性质

• 熔点：
  72.5-73 °C(Solv: ethanol (64-17-5))
• 沸点：
  340.4±25.0 °C(Predicted)
• 密度：
  1.080±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-<3-(trimethylsilyl)propyl>phthalimide 以 乙醇 为溶剂， 反应 2.0h， 生成 2-[2-Hydroxyethyl(3-trimethylsilylpropyl)amino]ethanol
  参考文献：
  名称：

  Lukevits,E.; Voronkov,M.G., Journal of general chemistry of the USSR, 1968, vol. 38, p. 2248 - 2250

  摘要：

  DOI：
• 作为产物：
  描述：

  3-(三甲硅基)-1-丙醇 在 三乙胺 、 sodium iodide 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 43.0h， 生成 N-<3-(trimethylsilyl)propyl>phthalimide
  参考文献：
  名称：

  Exploratory Studies of H-Atom Abstraction and Silyl-Transfer Photoreactions of Silylalkyl Ketones and (Silylalkyl)phthalimides

  摘要：

  Exploratory studies have been conducted to probe competitive H-atom abstraction and SET-promoted, silyl-transfer reactions of excited states of silylalkyl ketones and (silylalkyl)phthalimides. Photochemical investigations with the (silylalkyl)phthalimides have demonstrated that typical gamma-H atom abstraction reactions occur upon irradiation in less polar and less silophilic solvents. In contrast, irradiation of these substances in polar-protic-silophilic solvents results in product formation via pathways involving SET-induced desilylation. Photoreactions of silylamido-aryl ketones in either nonsilophilic or silophilic solvents take place almost exclusively by sequential SET silyl-transfer routes to produce azetidine products. Finally, the chemical selectivities of photochemical reactions of silylpropyl-aryl ketones appear to depend on medium polarity and silophilicity. Irradiation of these substrates in less polar-nonsilophilic solvents leads to almost exclusive formation of acetophenone and vinyltrimethylsilane in essentially equal yields by a reaction pathway initiated by gamma-H atom abstraction and 1,4-biradical fragmentation. However, irradiation of these substances in polar-silophilic solvents produces acetophenone and vinyltrimethylsilane in an ca. 1.7:1 ratio reflecting the fact that a silyl-transfer pathway competes with H-atom abstraction under these conditions.

  DOI：

  10.1021/jo9522623

文献信息

• Terminal C(sp ³ )–H borylation through intermolecular radical sampling
  作者：Miao Wang、Yahao Huang、Peng Hu

  DOI：10.1126/science.adj9258

  日期：2024.2.2

  Hydrogen atom transfer (HAT) processes can overcome the strong bond dissociation energies (BDEs) of inert C(sp 3 )–H bonds and thereby convert feedstock alkanes into value-added fine chemicals. Nevertheless, the high reactivity of HAT reagents, coupled with the small differences among various C(sp 3 )–H bond strengths, renders site-selective transformations of straight-chain alkanes a great challenge

  氢原子转移 (HAT) 过程可以克服惰性 C(sp) 的强键解离能 (BDE) 3 )–H键，从而将原料烷烃转化为高附加值的精细化学品。尽管如此，HAT 试剂的高反应活性，加上各种 C(sp 3 )–H键强度，使得直链烷烃的位点选择性转化成为一个巨大的挑战。在这里，我们提出了一种光催化分子间自由基采样过程，用于铁催化末端 C(sp 3 )–H 键存在于具有小空间位阻的底物中，包括无支链烷烃。机理研究表明，该反应通过可逆的 HAT 过程进行，然后进行碳自由基的选择性硼化。硼-亚砜络合物可能有助于观察到高末端区域选择性。
• WO2008/58999
  申请人：——

  公开号：——

  公开（公告）日：——
• DSA:  A New Internal Standard for NMR Studies in Aqueous Solution
  作者：James S. Nowick、Omid Khakshoor、Mehrnoosh Hashemzadeh、Justin O. Brower

  DOI：10.1021/ol035347w

  日期：2003.9.1

  [GRAPHICS]The widely used internal standard for NMR studies in aqueous solution DSS (sodium 4,4-dimethyl-4-silapentane-1-sulfonate) can interact with cationic peptides, diminishing its value for such studies. This paper introduces DSA (4,4-dimethyl-4-silapentane-1-ammonium trifluoroacetate) as a new internal standard that does not suffer from this problem.
• (Aminoalkyl)trimethylsilanes. A new class of monoamine oxidase inactivators
  作者：Richard B. Silverman、Gregory M. Banik

  DOI：10.1021/ja00241a070

  日期：1987.4
• Exploratory Studies of H-Atom Abstraction and Silyl-Transfer Photoreactions of Silylalkyl Ketones and (Silylalkyl)phthalimides
  作者：Yean Jang Lee、Rong Ling、Patrick S. Mariano、Ung Chan Yoon、Dong Uk Kim、Sun Wha Oh

  DOI：10.1021/jo9522623

  日期：1996.1.1

  Exploratory studies have been conducted to probe competitive H-atom abstraction and SET-promoted, silyl-transfer reactions of excited states of silylalkyl ketones and (silylalkyl)phthalimides. Photochemical investigations with the (silylalkyl)phthalimides have demonstrated that typical gamma-H atom abstraction reactions occur upon irradiation in less polar and less silophilic solvents. In contrast, irradiation of these substances in polar-protic-silophilic solvents results in product formation via pathways involving SET-induced desilylation. Photoreactions of silylamido-aryl ketones in either nonsilophilic or silophilic solvents take place almost exclusively by sequential SET silyl-transfer routes to produce azetidine products. Finally, the chemical selectivities of photochemical reactions of silylpropyl-aryl ketones appear to depend on medium polarity and silophilicity. Irradiation of these substrates in less polar-nonsilophilic solvents leads to almost exclusive formation of acetophenone and vinyltrimethylsilane in essentially equal yields by a reaction pathway initiated by gamma-H atom abstraction and 1,4-biradical fragmentation. However, irradiation of these substances in polar-silophilic solvents produces acetophenone and vinyltrimethylsilane in an ca. 1.7:1 ratio reflecting the fact that a silyl-transfer pathway competes with H-atom abstraction under these conditions.