1,2-Bis(trimethylsilyl)-2,3-butadiene | 105040-62-8

• 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: 1,2-Bis(trimethylsilyl)-2,3-butadiene
• CAS: 105040-62-8
• 化学式: C₁₀H₂₂Si₂
• 分子量: 198.456
• InChiKey: SZTDOYKMXTXPEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.91
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  1,2-Bis(trimethylsilyl)-2,3-butadiene 在 四丁基氟化铵 、 碘 、 碳酸氢钠 作用下， 生成 Silane, (4-iodo-2-butynyl)trimethyl-
  参考文献：
  名称：

  Preparation of 2-Iodo-1,3-butadienes from 1-Trimethylsilyl-2,3-butadienes and their Functionalizations

  摘要：

  Successive treatment of 1-trimethylsilyl-2,3-butadienes with iodine and tetra-n-butylammonium fluoride in the same flask affords 2-iodo-1,3-butadienes in good yields and their palladium-catalyzed carbonylation and alkynylation allows introduction of ester and alkynyl groups to the 2-position bearing an iodine atom leading to various 2,3-disubstituted 1,3-butadienes. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10413-0
• 作为产物：
  描述：

  三甲硅基丙炔醇 在 正丁基锂 、 lithium chloride 作用下， 以 四氢呋喃 为溶剂， 生成 1,2-Bis(trimethylsilyl)-2,3-butadiene
  参考文献：
  名称：

  Preparation of 2-Iodo-1,3-butadienes from 1-Trimethylsilyl-2,3-butadienes and their Functionalizations

  摘要：

  Successive treatment of 1-trimethylsilyl-2,3-butadienes with iodine and tetra-n-butylammonium fluoride in the same flask affords 2-iodo-1,3-butadienes in good yields and their palladium-catalyzed carbonylation and alkynylation allows introduction of ester and alkynyl groups to the 2-position bearing an iodine atom leading to various 2,3-disubstituted 1,3-butadienes. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10413-0

文献信息

• Stereoselective synthesis of both geometric isomers of γ-(trimethylsilyl)allylboranes and the diastereoselective condensations with aldehydes
  作者：Yu Gui Gu、Kung K. Wang

  DOI：10.1016/0040-4039(91)80678-y

  日期：1991.6

  Hydroboration of allenylsilanes 1 produces the Z isomers 10 as the kinetic product, leading to hydroxyallylsilanes 15 after condensation with hexanal, whereas the E isomers 4 and 12 are thermodynamically more stable, affording 9 predominantly.

  烯丙基硅烷1的氢硼化生成Z异构体10作为动力学产物，在与己醛缩合后生成羟基烯丙基硅烷15，而E异构体4和12在热力学上更稳定，主要得到9。
• Stereoselective synthesis of terminal 1,3-butadienes by the condensation reaction of aldehydes and ketones with .gamma.-trimethylsilyl-substituted allylboranes
  作者：Kung K. Wang、Chin Liu、Yu Gui Gu、Friedrich N. Burnett、Prem D. Sattsangi

  DOI：10.1021/jo00005a045

  日期：1991.3

  Allylboranes 7-12, readily prepared from allenylsilanes 1-6 by hydroboration with 9-borabicyclo[3.3.1]nonane, smoothly condense with aldehydes and ketones to afford, after basic or acidic workup to promote the Peterson olefination reaction, a variety of terminal 1,3-butadienes. The dienes derived from aldehydes have high isomeric purity except in the cases with allylborane 12. Apparently, high diastereoselectivity was obtained during the condensation step with 7-11 to form 14. In each case, by simply changing the workup conditions to induce syn or anti elimination of hydroxytrimethylsilane, either the Z or the E isomer of the diene was obtained.
• Stereoselective synthesis of 2-(trimethylsilyl)methyl-1,3-butadienes
  作者：Chin Liu、Kung K. Wang

  DOI：10.1021/jo00374a049

  日期：1986.11
• WANG, KUNG K.;LIU, CHIN;GU, YU GUI;BURNETT, FRIEDRICH;N. , SATTSANGI PREM+, J. ORG. CHEM., 56,(1991) N, C. 1914-1922
  作者：WANG, KUNG K.、LIU, CHIN、GU, YU GUI、BURNETT, FRIEDRICH、N. , SATTSANGI PREM+

  DOI：——

  日期：——
• LIU CHIN; WANG KUNG K., J. ORG. CHEM., 51,(1986) N 24, 4733-4734
  作者：LIU CHIN、 WANG KUNG K.

  DOI：——

  日期：——