1-三乙基甲硅烷基-1,2-丙二烯 | 111080-03-6

• 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
• 中文名称: 1-三乙基甲硅烷基-1,2-丙二烯
• 英文名称: 1-triethylsilyl-1,2-propadiene
• 英文别名: triethyl(propadienyl)silane
• CAS: 111080-03-6
• 化学式: C₉H₁₈Si
• 分子量: 154.327
• InChiKey: TZQXVIODSUJVOQ-UHFFFAOYSA-N

物化性质

• 沸点：
  164.4±7.0 °C(Predicted)
• 密度：
  0.747±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.38
• 重原子数：
  10
• 可旋转键数：
  4
• 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：

  1-三乙基甲硅烷基-1,2-丙二烯 在 gallium(III) trichloride 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 (E)-1-triethylsilyl-2-methyl-2-(2,4-dimethylphenyl)oxirane
  参考文献：
  名称：

  Aromatic alkenylation using electrophilic organogallium reagent generated from allenylsilane and GaCl3

  摘要：

  Aromatic hydrocarbons are alkenylated with silylallene in the presence of GaCl3 at -90 degreesC. Organometallic electrophiles generated from the allene and GaCl3 are the active species in this reaction. A modest level of ortho-selectivity is observed. While the silylallene reacts exclusively at the 2-position, 1,2-alkradiene reacts at the 1-position predominantly. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)01043-7
• 作为产物：
  描述：

  在 三氟乙酸 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以90%的产率得到1-三乙基甲硅烷基-1,2-丙二烯
  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

• Palladium-catalyzed Cycloaddition of Alkynyl Aryl Ethers to Allenes to Form a 2,3-Bismethylidene-2,3-dihydro-4<i>H</i>-1-benzopyran Framework
  作者：Yasunori Minami、Mayuko Kanda、Tamejiro Hiyama

  DOI：10.1246/cl.130894

  日期：2014.2.5

  Palladium-catalyzed cycloaddition of alkynyl aryl ethers to allenes proceeds through o-C–H activation to give 2,3-dihydro-4H-1-benzopyran derivatives containing 2,3-exo-double bonds. These benzopyr...

  钯催化的炔基芳基醚与丙二烯的环加成反应通过 oC-H 活化得到含有 2,3-外双键的 2,3-二氢-4H-1-苯并吡喃衍生物。这些苯并吡...
• Catalytic CH Bond Addition of Pyridines to Allenes by a Rare-Earth Catalyst
  作者：Guoyong Song、Baoli Wang、Masayoshi Nishiura、Zhaomin Hou

  DOI：10.1002/chem.201501121

  日期：2015.6.1

  The catalytic CH addition of pyridines to allenes has been achieved for the first time by using a half‐sandwich scandium catalyst, thus constituting a straightforward and atom‐economical route for the synthesis of alkenylated pyridine derivatives. The reaction proceeded regio‐ and stereoselectively, affording a new family of alkenylated pyridine compounds which are otherwise difficult to synthesize

  催化Ç 小时加入吡啶以丙二烯已经通过使用一个半夹心钪催化剂，因此构成为链烯基吡啶衍生物的合成和直截了当原子的经济的路线来实现首次。该反应在区域和立体选择性上进行，提供了新的烯基化吡啶化合物家族，否则很难合成。阳离子钪-η 2 -吡啶基物种分离并确认在该转化的关键催化剂物种。
• Copper‐Catalyzed Enantioselective and Regiodivergent Allylation of Ketones with Allenylsilanes
  作者：Menghua Xu、Qingbin Lu、Baihui Gong、Wenqing Ti、Aijun Lin、Hequan Yao、Shang Gao

  DOI：10.1002/anie.202311540

  日期：2023.10.26

  A CuH-catalyzed enantioselective and regiodivergent allyl addition to ketones with allenylsilanes has been developed. Various tertiary homoallylic alcohols bearing an alkenyl silane or an allyl silane group were synthesized with high regioselectivities and excellent enantioselectivities.

  已开发出 CuH 催化的烯丙基硅烷与酮的对映选择性和区域发散烯丙基加成反应。合成了各种带有烯基硅烷或烯丙基硅烷基团的高烯丙醇叔醇，具有高区域选择性和优异的对映选择性。
• Reaction of triethylsilane with propargyl chloride in the presence of the H2PtCl6-I2 catalytic system
  作者：V. B. Pukhnarevich、N. I. Ushakova、I. I. Tsykhanskaya、A. I. Albanov、M. G. Voronkov

  DOI：10.1007/bf00954045

  日期：1986.9
• Aromatic alkenylation using electrophilic organogallium reagent generated from allenylsilane and GaCl3
  作者：Yoshiyuki Kido、Fumi Yonehara、Masahiko Yamaguchi

  DOI：10.1016/s0040-4020(00)01043-7

  日期：2001.1

  Aromatic hydrocarbons are alkenylated with silylallene in the presence of GaCl3 at -90 degreesC. Organometallic electrophiles generated from the allene and GaCl3 are the active species in this reaction. A modest level of ortho-selectivity is observed. While the silylallene reacts exclusively at the 2-position, 1,2-alkradiene reacts at the 1-position predominantly. (C) 2001 Elsevier Science Ltd. All rights reserved.