Tert-butyl-[3-[tert-butyl(dimethyl)silyl]oxyhex-5-enoxy]-dimethylsilane | 483303-33-9

• 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-butyl-[3-[tert-butyl(dimethyl)silyl]oxyhex-5-enoxy]-dimethylsilane
• CAS: 483303-33-9
• 化学式: C₁₈H₄₀O₂Si₂
• 分子量: 344.685
• InChiKey: ULXUZWLOTALPDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.36
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Tert-butyl-[3-[tert-butyl(dimethyl)silyl]oxyhex-5-enoxy]-dimethylsilane 在 2,6-二甲基吡啶 、 二甲基硫 、 臭氧 作用下， 生成 (3S,5S)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-3-triisopropylsilanyloxy-1-trimethylsilanyl-hept-1-yne
  参考文献：
  名称：

  Synthesis of the core of apicularen A by transannular conjugate addition

  摘要：

  The synthesis of the core of the myxobacteria metabolite apicularen A by a novel transannular 1,4-addition is described. The key step involved acid mediated transannular conjugate addition of the C13 hydroxyl into the a,p-unsaturated ketone in macrolactone 18 to provide the trans-pyranone 19 and the cis-isomer 20 in a ratio of 9:1, respectively. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02069-5
• 作为产物：
  描述：

  3-(叔丁基-二甲基-硅烷基OXY)-丙醛 在 咪唑 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 Tert-butyl-[3-[tert-butyl(dimethyl)silyl]oxyhex-5-enoxy]-dimethylsilane
  参考文献：
  名称：

  Gold-Catalyzed Heterocycle Synthesis Using Homopropargylic Ethers as Latent Electrophiles

  摘要：

  Homopropargylic ethers with pendent nucleophiles, when subjected to Au catalysts in aqueous solvent, provide heterocyclic ketones. The reactions are efficient, tolerant of functionality and ambient atmosphere, and operationally simple. Diastereoselectivity can be predicted on the basis of product thermodynamics. This process demonstrates the viability of homopropargylic ethers to serve as latent electrophiles that can be unraveled under highly selective conditions to promote heterocycle formation through nucleophilic additions to alpha,beta-unsaturated ketones.

  DOI：

  10.1021/ol060574u

文献信息

• Hydrazone and Oxime Olefination via Ruthenium Alkylidenes
  作者：Daniel J. Nasrallah、Troy E. Zehnder、Jacob R. Ludwig、Daniel C. Steigerwald、John J. Kiernicki、Nathaniel K. Szymczak、Corinna S. Schindler

  DOI：10.1002/anie.202112101

  日期：2022.5.23

  Olefination of carbon–heteroatom double bonds is a powerful approach to access highly functionalized olefins. An approach is reported here that uses air-stable and commercially available ruthenium alkylidenes to promote C=N/olefin ring closure. The enabling strategy for this reaction is the use of hydrazones and oximes as readily accessible substrates that preferentially react with ruthenium alkylidenes

  碳-杂原子双键的烯化是获得高度官能化烯烃的有效方法。此处报告了一种方法，该方法使用空气稳定且市售的亚烷基钌来促进 C=N/烯烃环闭合。该反应的可行策略是使用腙和肟作为易于获得的底物，即使在羰基存在的情况下，它们也优先与亚烷基钌反应。
• Gold-Catalyzed Heterocycle Synthesis Using Homopropargylic Ethers as Latent Electrophiles
  作者：Hyung Hoon Jung、Paul E. Floreancig

  DOI：10.1021/ol060574u

  日期：2006.4.1

  Homopropargylic ethers with pendent nucleophiles, when subjected to Au catalysts in aqueous solvent, provide heterocyclic ketones. The reactions are efficient, tolerant of functionality and ambient atmosphere, and operationally simple. Diastereoselectivity can be predicted on the basis of product thermodynamics. This process demonstrates the viability of homopropargylic ethers to serve as latent electrophiles that can be unraveled under highly selective conditions to promote heterocycle formation through nucleophilic additions to alpha,beta-unsaturated ketones.
• Synthesis of the core of apicularen A by transannular conjugate addition
  作者：Ferdows Hilli、Jonathan M. White、Mark A. Rizzacasa

  DOI：10.1016/s0040-4039(02)02069-5

  日期：2002.11

  The synthesis of the core of the myxobacteria metabolite apicularen A by a novel transannular 1,4-addition is described. The key step involved acid mediated transannular conjugate addition of the C13 hydroxyl into the a,p-unsaturated ketone in macrolactone 18 to provide the trans-pyranone 19 and the cis-isomer 20 in a ratio of 9:1, respectively. (C) 2002 Elsevier Science Ltd. All rights reserved.