4-Chloro-1-[methyl(diphenyl)silyl]butan-1-one | 144668-09-7

• 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: 4-Chloro-1-[methyl(diphenyl)silyl]butan-1-one
• CAS: 144668-09-7
• 化学式: C₁₇H₁₉ClOSi
• 分子量: 302.876
• InChiKey: PBSBMJUMTCSBFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 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：

  4-Chloro-1-[methyl(diphenyl)silyl]butan-1-one 在 potassium iodide 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 8.0h， 以94%的产率得到5-methyldiphenylsilyl-2,3-dihydrofuran
  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：

  甲基二苯基氯硅烷 在 正丁基锂 、 Celite 、 三氟化硼乙醚 、 mercury(II) oxide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.0h， 生成 4-Chloro-1-[methyl(diphenyl)silyl]butan-1-one
  参考文献：
  名称：

  The Scope and Limitations of Intramolecular Radical Cyclizations of Acylsilanes with Alkyl, Aryl, and Vinyl Radicals

  摘要：

  5-Exo cyclizations of primary and secondary radicals with acylsilanes successfully give cyclopentyl silyl ethers. The corresponding 6-exo cyclizations are sensitive to changes of the size of silyl groups. Secondary radicals undergo 6-exo cyclizations with acylsilanes more slowly. Reaction of aryl radical with acylsilane proceeds well for 5-exo cyclization but not for 6-exo cyclization. Vinyl radicals give best results in 5-exo cyclizations with acylsilanes but give low yields (similar to 30%) in 6-exo cyclizations. Intramolecular cyclizations of vinyl radicals with acylsilanes give enol silyl ethers regiospecifically.

  DOI：

  10.1021/jo9711302

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 Scope and Limitations of Intramolecular Radical Cyclizations of Acylsilanes with Alkyl, Aryl, and Vinyl Radicals
  作者：Sheng-Yueh Chang、Weir-Torn Jiaang、Chaur-Donp Cherng、Kuo-Hsiang Tang、Chih-Hao Huang、Yeun-Min Tsai

  DOI：10.1021/jo9711302

  日期：1997.12.1

  5-Exo cyclizations of primary and secondary radicals with acylsilanes successfully give cyclopentyl silyl ethers. The corresponding 6-exo cyclizations are sensitive to changes of the size of silyl groups. Secondary radicals undergo 6-exo cyclizations with acylsilanes more slowly. Reaction of aryl radical with acylsilane proceeds well for 5-exo cyclization but not for 6-exo cyclization. Vinyl radicals give best results in 5-exo cyclizations with acylsilanes but give low yields (similar to 30%) in 6-exo cyclizations. Intramolecular cyclizations of vinyl radicals with acylsilanes give enol silyl ethers regiospecifically.
• 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.