1-bromo-1-(trimethylsilyl)propadiene | 38002-44-7

• 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: 1-bromo-1-(trimethylsilyl)propadiene
• 英文别名: 1-bromo-1-trimethylsilylpropadiene；1-Brom-1-trimethylsilylallen
• CAS: 38002-44-7
• 化学式: C₆H₁₁BrSi
• 分子量: 191.143
• InChiKey: CZGPMSCZZVWCQU-UHFFFAOYSA-N

物化性质

• 沸点：
  160.8±10.0 °C(Predicted)
• 密度：
  1.124±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.93
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-bromo-1-(trimethylsilyl)propadiene 在 titanium(IV) isopropylate 、 四丁基氟化铵 、 异丙基氯化镁 作用下， 生成
  参考文献：
  名称：

  A novel propargyltitanation of acetylenes. Heteroatom substituent-dependent manifold in intermolecular coupling of allene and acetylene

  摘要：

  Titanium alkoxide-mediated coupling of functionalized allenes and acetylenes afforded various types of producuts, and the first propargyltitanation of acetylenes was achieved by the appropriate choice of allenes. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.11.049
• 作为产物：
  描述：

  在 N-溴代丁二酰亚胺(NBS) 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 以90%的产率得到1-bromo-1-(trimethylsilyl)propadiene
  参考文献：
  名称：

  Regioselective Allene Synthesis and Propargylations with Propargyl Diethanolamine Boronates

  摘要：

  The utility of propargyl diethanolamine boronates as reagents for the preparation of allenes and homopropargylic alcohols is presented. Protonolysis with TFA and electrophilic substitution with N-halosuccinimides proceeded with inversion to provide the corresponding allene in high yield and regioselectivity. Alternatively, the propargylation of aldehydes was achieved with use of the in situ generated lithiated complex.

  DOI：

  10.1021/ol9022529

文献信息

• Bogoradovskii, E. T.; Zavgorodnii, V. S.; Liepin'sh, E. E., Journal of general chemistry of the USSR, 1991, vol. 61, # 6.2, p. 1295 - 1306
  作者：Bogoradovskii, E. T.、Zavgorodnii, V. S.、Liepin'sh, E. E.、Birgele, I. S.、Petrov, A. A.

  DOI：——

  日期：——
• Bogoradovskii, E. T.; Zavgorodnii, V. S.; Liepin'sh, E. E., Journal of general chemistry of the USSR, 1991, vol. 61, p. 1295 - 1306
  作者：Bogoradovskii, E. T.、Zavgorodnii, V. S.、Liepin'sh, E. E.、Birgele, I. S.、Petrov, A. A.

  DOI：——

  日期：——
• Regioselective Allene Synthesis and Propargylations with Propargyl Diethanolamine Boronates
  作者：Daniel R. Fandrick、Jonathan T. Reeves、Zhulin Tan、Heewon Lee、Jinhua J. Song、Nathan K. Yee、Chris H. Senanayake

  DOI：10.1021/ol9022529

  日期：2009.12.3

  The utility of propargyl diethanolamine boronates as reagents for the preparation of allenes and homopropargylic alcohols is presented. Protonolysis with TFA and electrophilic substitution with N-halosuccinimides proceeded with inversion to provide the corresponding allene in high yield and regioselectivity. Alternatively, the propargylation of aldehydes was achieved with use of the in situ generated lithiated complex.
• A novel propargyltitanation of acetylenes. Heteroatom substituent-dependent manifold in intermolecular coupling of allene and acetylene
  作者：Ryoichi Tanaka、Misa Sasaki、Fumie Sato、Hirokazu Urabe

  DOI：10.1016/j.tetlet.2004.11.049

  日期：2005.1

  Titanium alkoxide-mediated coupling of functionalized allenes and acetylenes afforded various types of producuts, and the first propargyltitanation of acetylenes was achieved by the appropriate choice of allenes. (C) 2004 Elsevier Ltd. All rights reserved.