5-chloro-1-(methyldiphenylsilyl)pentan-1-one | 135746-51-9

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: 5-chloro-1-(methyldiphenylsilyl)pentan-1-one
• 英文别名: 5-Chloro-1-[methyl(diphenyl)silyl]pentan-1-one
• CAS: 135746-51-9
• 化学式: C₁₈H₂₁ClOSi
• 分子量: 316.903
• InChiKey: COSSQLIHGFEYPB-UHFFFAOYSA-N

物化性质

• 沸点：
  397.9±34.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 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：

  5-chloro-1-(methyldiphenylsilyl)pentan-1-one 在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 2.0h， 以89%的产率得到5-iodo-1-(methyldiphenylsilyl)pentan-1-one
  参考文献：
  名称：

  The formation of oxygen-containing heterocycles via intramolecular cyclizations of halo-substituted acylsilanes and unsaturated acylsilanes

  摘要：

  Halo-substituted acylsilanes undergo cyclizations easily when heated in a polar solvent such as NMP to afford 2-silyldihydrofurans and 2-silyldihydropyrans. Unsaturated acylsilanes undergo cyclizations through reactions with iodine, phenylselenenyl bromide, or chloride. Further reactions of the cyclized products with pyridinium perbromide, phenylselenenyl bromide, or chloride give highly functionalized dihydrofurans and dihydropyrans. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00936-9
• 作为产物：
  描述：

  2-methyldiphenylsilyl-1,3-dithiane 在 正丁基锂 、 Celite 、 三氟化硼乙醚 、 mercury(II) oxide 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 5-chloro-1-(methyldiphenylsilyl)pentan-1-one
  参考文献：
  名称：

  Intramolecular free radical cyclizations using acylsilanes as radicalphiles

  摘要：

  Carbon radicals add intramolecularly to acylsilanes at the carbonyl carbon followed by radical Brook rearrangement to give silylated cyclopentanols or cyclohexanols in good yields.

  DOI：

  10.1016/0040-4039(91)80820-v

文献信息

• Cyclizations of functionalized acylsilanes to form 2-silyldihydropyrans and 2-silyldihydrofurans
  作者：Yeun Min Tsai、Hong Chang Nieh、Chaur Donp Cherng

  DOI：10.1021/jo00052a006

  日期：1992.12

  Cyclizations of (delta-haloacyl)- and (gamma-haloacyl)silanes in a polar aprotic solvent gave 2-silyldihydropyrans and 2-silyldihydrofurans in good yields. This new type of cyclization could also be initiated by a carbocation and an olefin.
• The formation of oxygen-containing heterocycles via intramolecular cyclizations of halo-substituted acylsilanes and unsaturated acylsilanes
  作者：Yeun-Min Tsai、Chaur-Donp Cherng、Hong-Chang Nieh、Jiuen-Ahn Sieh

  DOI：10.1016/s0040-4020(99)00936-9

  日期：1999.12

  Halo-substituted acylsilanes undergo cyclizations easily when heated in a polar solvent such as NMP to afford 2-silyldihydrofurans and 2-silyldihydropyrans. Unsaturated acylsilanes undergo cyclizations through reactions with iodine, phenylselenenyl bromide, or chloride. Further reactions of the cyclized products with pyridinium perbromide, phenylselenenyl bromide, or chloride give highly functionalized dihydrofurans and dihydropyrans. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Intramolecular free radical cyclizations using acylsilanes as radicalphiles
  作者：Yeun-Min Tsai、Chaur-Donp Cherng

  DOI：10.1016/0040-4039(91)80820-v

  日期：1991.7

  Carbon radicals add intramolecularly to acylsilanes at the carbonyl carbon followed by radical Brook rearrangement to give silylated cyclopentanols or cyclohexanols in good yields.