Butyl(trimethylsilyl)ketene | 71985-41-6

• 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: Butyl(trimethylsilyl)ketene
• CAS: 71985-41-6
• 化学式: C₉H₁₈OSi
• 分子量: 170.327
• InChiKey: WWOZYODFTOAQNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.81
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  Butyl(trimethylsilyl)ketene 、 正己醛 以62%的产率得到
  参考文献：
  名称：

  Black T. Howard, Zhang Yorg, Huang Jianhua, Smith Douglas C., Yates Bryan+, Synth. Commun, 25 (1995) N 1, S 15-20

  摘要：

  DOI：
• 作为产物：
  描述：

  2-Trimethylsilylcapronsaeure 在 草酰氯 、 溴 、 N,N-二甲基甲酰胺 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 Butyl(trimethylsilyl)ketene
  参考文献：
  名称：

  The highly enantioselective transformation of silylketenes into α-silylthioesters catalysed by cinchona alkaloids

  摘要：

  The reaction of silylketenes with thiophenol, mediated by cinchona alkaloid catalysts, proceeds to give alpha -silylthioester products in good chemical yield and with enantiomeric excess values in the range 79-93%. The absolute configuration of one of the thioester products was determined by X-ray diffraction. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00304-5

文献信息

• Novel synthesis of ynolates via the cleavage of ester dianions: α-Bromo and α,α-dibromo esters as precursors
  作者：Mitsuru Shindo、Yusuke Sato、Kozo Shishido

  DOI：10.1016/s0040-4020(98)00006-4

  日期：1998.3

  ester dianions. The key intermediates, ester dianions, were generated from α-bromocarboxylic acid ester enolates via lithium halogen exchange. α,α-Dibromocarboxylic acid ester also gives lithium amide free ynolates by addition of tert-BuLi. The reactions of ynolates, generated by this novel and convenient method, with aldehydes to give β-lactons are discussed.

  壬酸酯是通过热引发的酯二价阴离子裂解而合成的。α-溴羧酸酯烯酸酯通过卤化锂交换生成了关键中间体酯二价阴离子。通过添加叔丁基锂，α，α-二溴代羧酸酯也可提供不含酰胺基锂的羟基乙酸。讨论了通过这种新颖且方便的方法生成的炔诺酸酯与醛类反应生成β-内酯的方法。
• Carbonyl Homologation via β-Trimethylsilyl β-Lactone Rearrangements. A Nonbasic Alternative to the Wittig Reaction
  作者：T. Howard Black、Yong Zhang、Jianhua Huang、Douglas C. Smith、Bryan E. Yates

  DOI：10.1080/00397919508010783

  日期：1995.1

  Saturated and unsaturated aldehydes and ketones, when treated with trimethylsilylketene and BF3 for 16 hours, form beta-lactones which spontaneously rearrange to alpha, beta-unsaturated TMS esters; these hydrolyze during workup to form the corresponding carboxylic acids.
• A Convenient Synthesis of Iodotrimethylsilane and its Use in the Preparation of Silylketenes
  作者：Hideki Sakurai、Akihiko Shirahata、Koshi Sasaki、Akira Hosomi

  DOI：10.1055/s-1979-28823

  日期：——
• A synthesis of ynolates via the cleavage of ester dianions
  作者：Mitsuru Shindo

  DOI：10.1016/s0040-4039(97)00924-6

  日期：1997.6

  A new method for ynolate synthesis via the cleavage of ester dianions has been developed. The key intermediates, ester dianions, generated from alpha-bromocarboxylic acid ester enolates via lithium-halogen exchange turned out to be so labile that they were cleaved rapidly to give ynolates. (C) 1997 Elsevier Science Ltd.
• SAKURAI HIDEKI; SHIRAHATA AKIHIKO; SASAKI KOSHI; HOSOMI AKIRA, SYNTHESIS, 1979, NO 9, 740-1
  作者：SAKURAI HIDEKI、 SHIRAHATA AKIHIKO、 SASAKI KOSHI、 HOSOMI AKIRA

  DOI：——

  日期：——