(tert-butyldimethylsilyl)ethoxyacetylene | 124513-26-4

• 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: (tert-butyldimethylsilyl)ethoxyacetylene
• 英文别名: tert-butyl(ethoxyethynyl)dimethylsilane；Tert-butyl-(2-ethoxyethynyl)-dimethylsilane
• CAS: 124513-26-4
• 化学式: C₁₀H₂₀OSi
• 分子量: 184.354
• InChiKey: SGLXOIZAQAOURF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.03
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (tert-butyldimethylsilyl)ethoxyacetylene 以86%的产率得到tert-butyldimethylsilylketene
  参考文献：
  名称：

  An efficient synthesis of .alpha.-silylacetates having various types of functional groups in the molecules

  摘要：

  DOI：

  10.1021/jo00290a058
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 、 乙氧基乙炔 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以74%的产率得到(tert-butyldimethylsilyl)ethoxyacetylene
  参考文献：
  名称：

  摘要：

  Silylation and germylation of trialkylsilyl(germyl)ethoxyacetylenes containing bulky substituents at the silicon or germanium atom were performed. In all cases, the corresponding bis-organoelement-containing ketenes were obtained as the only reaction products. No intermediate isomeric ynol ethers were detected by spectroscopy.

  DOI：

  10.1023/a:1011393908126

文献信息

• Access to Substituted Indenol Ethers via a Regioselective Intermolecular Carbopalladation Cascade
  作者：Brandon L. Coles-Taylor、Mitchell L. Ellinwood、Maximilian S. McCallum、Sara L. McCormack、Meredith H. Jones、Andrés G. Muñoz、Brian W. Michel

  DOI：10.1021/acs.joc.2c02213

  日期：2022.12.16

  can rapidly generate multiple new C–C bonds; however, regioselectivity is challenging for intermolecular variants. Using ynol ethers, we observe complete regiocontrol of migratory insertion followed by a second migratory insertion with a pendant alkene to turn-over the catalytic cycle. The resulting products are oligosubstituted 1-indenol ethers with defined stereochemistry based on the initial alkene

  炔碳钯化反应可以快速生成多个新的C-C键；然而，区域选择性对于分子间变体具有挑战性。使用炔醇醚，我们观察到迁移插入的完全区域控制，然后是带有悬垂烯烃的第二次迁移插入以翻转催化循环。所得产物是低聚取代的 1-茚醇醚，具有基于初始烯烃几何结构的明确立体化学。阻断 β-氢化物消除允许 C-H 和 C-C 还原消除步骤进行催化剂周转。
• KITA, YASUYUKI;SEKIHACHI, JUN-ICHI;HAYASHI, YOSHIKAZU;DA, YONG-ZHONG;YAMA+, J. ORG. CHEM., 55,(1990) N, C. 1108-1112
  作者：KITA, YASUYUKI、SEKIHACHI, JUN-ICHI、HAYASHI, YOSHIKAZU、DA, YONG-ZHONG、YAMA+

  DOI：——

  日期：——
• An efficient synthesis of .alpha.-silylacetates having various types of functional groups in the molecules
  作者：Yasuyuki Kita、Junichi Sekihachi、Yoshikazu Hayashi、Yong Zhong Da、Miki Yamamoto、Shuji Akai

  DOI：10.1021/jo00290a058

  日期：1990.2
• ——
  作者：S. V. Ponomarev、A. S. Zolotareva、A. S. Leont"ev、Yu. V. Kuznetsov、V. S. Petrosyan

  DOI：10.1023/a:1011393908126

  日期：——

  Silylation and germylation of trialkylsilyl(germyl)ethoxyacetylenes containing bulky substituents at the silicon or germanium atom were performed. In all cases, the corresponding bis-organoelement-containing ketenes were obtained as the only reaction products. No intermediate isomeric ynol ethers were detected by spectroscopy.