(1-bromoethenyl)chlorodiethylsilane

• 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-bromoethenyl)chlorodiethylsilane
• 英文别名: 1-Bromoethenyl-chloro-diethylsilane
• 化学式: C₆H₁₂BrClSi
• 分子量: 227.604
• InChiKey: LFRMXCVXEWQWJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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-bromoethenyl)chlorodiethylsilane 在 喹啉 作用下， 生成 Diethylethinyl-chlorsilan
  参考文献：
  名称：

  VICINAL DEHYDROBROMINATION OF (α-BROMOVINYL)CHLOROSILANES WITH QUINOLINE. A NEW ROUTE TO ETHYNYLCHLOROSILANES

  摘要：

  (研究发现，CH2=CBrSiRnCl3-n（R = Me, Et; n = 0, 1, 2）型（α-溴乙烯基）氯硅烷与喹啉进行脱溴反应，可生成相应的乙炔基氯硅烷。

  DOI：

  10.1246/cl.1979.1287
• 作为产物：
  描述：

  溴乙烯 、 二氯二乙基硅烷 在 正丁基锂 、 lithium bromide 作用下， 以 四氢呋喃 、 乙醚 、 正戊烷 为溶剂， 反应 0.5h， 以26%的产率得到(1-bromoethenyl)chlorodiethylsilane
  参考文献：
  名称：

  1-Bromo-1-lithioethene:  A Practical Reagent in Organic Synthesis

  摘要：

  A reliable preparative scale synthesis of 1-bromo-1-lithioethene is reported. This reagent undergoes clean 1,2-addition with a range of aldehydes and ketones at -110 degrees C to afford the corresponding 2-bromo-1-alken-3-ols in moderate to excellent yield. Trapping with other electrophiles (acylsilanes, chlorosilanes, tributyltin chloride, iodine) cleanly provides practically useful yields of various 1-substituted 1-bromoethene products. Unexpectedly high diastereoselectivities were observed during the addition of 1-bromo-1-lithioethene to alpha-siloxy aldehydes (typically 10:1, Felkin-Ahn control) and protected ketopyranose and ketofuranose sugars (>= 10:1, addition from the less-hindered face). The title organolithium reagent possesses relatively low basicity at low temperature, and is compatible with a variety of common protecting groups. We believe that these unusual properties of 1-bronio-1-lithioethene may originate from the specific crystalline structure of the reagent in which lithium is coordinatively saturated and thus unavailable for chelation.

  DOI：

  10.1021/jo051125v

文献信息

• MATSUMOTO HIDEYUKI; KATO TAKAYUKI; MATSUBARA IKUYA; HOSHINO YOSHIKAZU; NA+, CHEM. LETT., 1979, NO 10, 1287-1290
  作者：MATSUMOTO HIDEYUKI、 KATO TAKAYUKI、 MATSUBARA IKUYA、 HOSHINO YOSHIKAZU、 NA+

  DOI：——

  日期：——
• 1-Bromo-1-lithioethene:  A Practical Reagent in Organic Synthesis
  作者：Yehor Y. Novikov、Paul Sampson

  DOI：10.1021/jo051125v

  日期：2005.12.1

  A reliable preparative scale synthesis of 1-bromo-1-lithioethene is reported. This reagent undergoes clean 1,2-addition with a range of aldehydes and ketones at -110 degrees C to afford the corresponding 2-bromo-1-alken-3-ols in moderate to excellent yield. Trapping with other electrophiles (acylsilanes, chlorosilanes, tributyltin chloride, iodine) cleanly provides practically useful yields of various 1-substituted 1-bromoethene products. Unexpectedly high diastereoselectivities were observed during the addition of 1-bromo-1-lithioethene to alpha-siloxy aldehydes (typically 10:1, Felkin-Ahn control) and protected ketopyranose and ketofuranose sugars (>= 10:1, addition from the less-hindered face). The title organolithium reagent possesses relatively low basicity at low temperature, and is compatible with a variety of common protecting groups. We believe that these unusual properties of 1-bronio-1-lithioethene may originate from the specific crystalline structure of the reagent in which lithium is coordinatively saturated and thus unavailable for chelation.
• VICINAL DEHYDROBROMINATION OF (α-BROMOVINYL)CHLOROSILANES WITH QUINOLINE. A NEW ROUTE TO ETHYNYLCHLOROSILANES
  作者：Hideyuki Matsumoto、Takayuki Kato、Ikuya Matsubara、Yoshikazu Hoshino、Yoichiro Nagai

  DOI：10.1246/cl.1979.1287

  日期：1979.10.5

  (α-Bromovinyl)chlorosilanes of the type CH2=CBrSiRnCl3−n(R = Me, Et; n = 0, 1, 2) were found to be dehydrobrominated with quinoline yielding the corresponding ethynylchlorosilanes.

  (研究发现，CH2=CBrSiRnCl3-n（R = Me, Et; n = 0, 1, 2）型（α-溴乙烯基）氯硅烷与喹啉进行脱溴反应，可生成相应的乙炔基氯硅烷。