(2-溴-1-苯基乙氧基)三甲基硅烷 | 35952-70-6

• 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-溴-1-苯基乙氧基)三甲基硅烷
• 英文名称: (2-Bromo-1-phenylethoxy)-trimethylsilane
• CAS: 35952-70-6
• 化学式: C₁₁H₁₇BrOSi
• 分子量: 273.245
• InChiKey: ICFRRMMSLKIRTC-UHFFFAOYSA-N

物化性质

• 沸点：
  69-71 °C(Press: 0.06 Torr)
• 密度：
  1.199±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.97
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2-溴-1-苯基乙氧基)三甲基硅烷 在 氯化亚砜 、 potassium carbonate 作用下， 以 乙醇 、 氯仿 为溶剂， 生成
  参考文献：
  名称：

  （R）-和（S）-N-（2-氯乙基）-N-甲基-2-苯基-2-羟乙基胺和相关试剂的不可逆肾上腺素受体拮抗作用。

  摘要：

  DOI：

  10.1021/jm00259a015
• 作为产物：
  描述：

  氧化苯乙烯 、 三甲基溴硅烷 以 氯仿 为溶剂， 以71%的产率得到(2-溴-1-苯基乙氧基)三甲基硅烷
  参考文献：
  名称：

  Syntheses of Alkyl Bromides from Ethers and Bromotrimethylsilane

  摘要：

  DOI：

  10.1055/s-1981-29460

文献信息

• Reactions d'halogeno-2, -3 et -4 alcoxysilanes avec le magnesium: resultants experimentaux et etude du mecanisme
  作者：Pierre Fostein、Jean-Claude Pommier

  DOI：10.1016/s0022-328x(00)84722-1

  日期：1978.5
• Formation et stabilité des carbénoïdes monohalogénés β-éthers
  作者：R. Tarhouni、B. Kirschleger、J. Villieras

  DOI：10.1016/0022-328x(88)87012-8

  日期：1988.5
• Halogénoalcoxyétains
  作者：Bernard Delmond、Jean-Claude Pommier、Jacques Valade

  DOI：10.1016/s0022-328x(00)86886-2

  日期：1972.2
• Addition of Dialkylzinc to Ketones in the Presence of Silylating Agents:  Synthesis of Functionalized Tertiary Silyl Ethers
  作者：Chiara Alvisi、Sonia Casolari、Anna Luisa Costa、Monica Ritiani、Emilio Tagliavini

  DOI：10.1021/jo971639x

  日期：1998.2.1
• Novel and Efficient Azomethine Ylide Forming Photoreactions of N-(Silylmethyl)phthalimides and Related Acid and Alcohol Derivatives
  作者：Ung Chan Yoon、Dong Uk Kim、Chan Woo Lee、Young Sun Choi、Yean-Jang Lee、Herman L. Ammon、Patrick S. Mariano

  DOI：10.1021/ja00115a004

  日期：1995.3

  An investigation of the photochemistry of N-(silylmethyl)phthalimides and related alpha-phthaloylacetic acids and 2-phenylethanol derivatives has uncovered new excited state processes resulting in the formation of azomethine ylide intermediates. Irradiation of N-[(trimethylsilyl)methyl]phthalimide in MeCN promotes C to O silyl transfer to generate the corresponding azomethine ylide which is efficiently trapped by reaction with water to yield the N-methylphthalimide or by dipolar cycloaddition with acetone, methyl acrylate, or acrylonitrile. Cycloadditions with the latter two dipolarophiles are both regioselective and endo-stereoselective. These processes can be triplet photosensitized by use of acetophenone. The related N-[(trimethylsilyl)methyl]-1,8-naphthalimide reacts in a similar manner upon irradiation in MeCN solutions containing the dipolarophiles methyl acrylate and acrylonitrile to produce cycloadducts which undergo spontaneous elimination of TMSOH, yielding alpha,beta-unsaturated ester or nitrile products. The ylide formed by irradiation of the (silylmethyl)phthalimide is trapped in a stereospecific (retention) manner by the dipolarophiles trans-hex-4-en-3-one, dimethyl maleate, and dimethyl fumarate. The effect of aryl ring substitution on the regiochemical course of the photoinduced C to O silyl migration process was probed by use of the 4-methoxy- and 4-carbomethoxyl-N-(silylmethyl)phthalimides. Irradiation of the former substance in an MeCN solution containing acrylonitrile gives rise to a single adduct whose structure suggests that silyl migration to oxygen of the carbonyl meta to the OMe substituent is highly favored. In contrast, the 4-carbomethoxyphthalimide is converted under these conditions to a mixture of regioisomeric adducts. Thus, silyl migration in the excited state of this substance is nonselective. In accord with hints found in earlier observations made by Kanaoka (Chem. Pharm. Bull. 1982, 30, 1263), N-phthalimide derivatives of the alpha-amino acids glycine, alanine, and phenylalanine undergo similar ylide forming photoreactions upon irradiation in MeCN solutions. The azomethine ylides produced by photodecarboxylation of these substances are efficiently trapped by dipolarophiles, and the overall photoreactions starting with the alanine and phenylalanine derivatives are highly stereoselective. Finally, the N-phthalimide derivative of 2-amino-1-phenylethanol also is transformed to a related ylide upon irradiation in MeCN. The nature, regiochemical and stereochemical course, and mechanistic interpretation of these new azomethine ylide forming photoreactions are discussed in this publication.