Cyclopentyl-bis(3-methoxyprop-1-ynyl)-(2-methylhex-5-en-2-yloxy)silane | 819048-82-3

• 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: Cyclopentyl-bis(3-methoxyprop-1-ynyl)-(2-methylhex-5-en-2-yloxy)silane
• CAS: 819048-82-3
• 化学式: C₂₀H₃₂O₃Si
• 分子量: 348.558
• InChiKey: AUTIMGBGYDZISF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.02
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Cyclopentyl-bis(3-methoxyprop-1-ynyl)-(2-methylhex-5-en-2-yloxy)silane 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) sodium hydride 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 生成 10a-Cyclopentyl-6-methoxymethyl-2,2-dimethyl-2,3,4,8,9,10a-hexahydro-1,10-dioxa-10a-sila-heptalene
  参考文献：
  名称：

  Tandem dienyne ring-closing metathesis of alkynyl silaketals for the formation of bicyclic siloxanes

  摘要：

  The tandem dienyne ring-closing metathesis of alkynyl silaketals containing two tethered olefins was achieved with second generation Grubbs NHC-ruthenium carbene complex to provide bicyclic siloxanes in good to excellent yield. Silaketals synthesized from homoallylic or bishomoallylic alcohols via base-catalyzed alcoholysis of trialkynylsilanes were well tolerated in the metathesis process and generated ring systems of various sizes. Removal of the silicon tether was achieved through protodesilylation with fluoride to afford stereochemically defined (1E,3Z)-dienes. (c) 2005 Elsevier B.V. All rights preserved.

  DOI：

  10.1016/j.jorganchem.2005.04.037
• 作为产物：
  描述：

  环戊基三氯硅烷 在 正丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 生成 Cyclopentyl-bis(3-methoxyprop-1-ynyl)-(2-methylhex-5-en-2-yloxy)silane
  参考文献：
  名称：

  Efficient Synthesis of Alkynylsilyl Ethers and Silaketals via Base-Induced Alkynylsilane Alcoholysis

  摘要：

  The efficient silylation of alcohols with di- and trialkynylsilanes was achieved under base-catalyzed conditions to afford alkynyl silyl ethers and symmetrical alkynyl silaketals in good yield. A selective alcoholysis of dialkynyl silyl ethers to mixed silaketals was also demonstrated. These products served as substrates for enyne ring-closing metathesis and, consequently, as precursors to stereochemically defined 1,3-dienes.

  DOI：

  10.1021/jo048908l

文献信息

• Efficient Synthesis of Alkynylsilyl Ethers and Silaketals via Base-Induced Alkynylsilane Alcoholysis
  作者：Jonathan B. Grimm、Daesung Lee

  DOI：10.1021/jo048908l

  日期：2004.12.1

  The efficient silylation of alcohols with di- and trialkynylsilanes was achieved under base-catalyzed conditions to afford alkynyl silyl ethers and symmetrical alkynyl silaketals in good yield. A selective alcoholysis of dialkynyl silyl ethers to mixed silaketals was also demonstrated. These products served as substrates for enyne ring-closing metathesis and, consequently, as precursors to stereochemically defined 1,3-dienes.
• Tandem dienyne ring-closing metathesis of alkynyl silaketals for the formation of bicyclic siloxanes
  作者：Jonathan B. Grimm、Ryan D. Otte、Daesung Lee

  DOI：10.1016/j.jorganchem.2005.04.037

  日期：2005.12

  The tandem dienyne ring-closing metathesis of alkynyl silaketals containing two tethered olefins was achieved with second generation Grubbs NHC-ruthenium carbene complex to provide bicyclic siloxanes in good to excellent yield. Silaketals synthesized from homoallylic or bishomoallylic alcohols via base-catalyzed alcoholysis of trialkynylsilanes were well tolerated in the metathesis process and generated ring systems of various sizes. Removal of the silicon tether was achieved through protodesilylation with fluoride to afford stereochemically defined (1E,3Z)-dienes. (c) 2005 Elsevier B.V. All rights preserved.