But-3-enyloxy-cyclopentyl-(1,1-dimethyl-pent-4-enyloxy)-(3-methoxy-prop-1-ynyl)-silane | 873435-83-7

• 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: But-3-enyloxy-cyclopentyl-(1,1-dimethyl-pent-4-enyloxy)-(3-methoxy-prop-1-ynyl)-silane
• 英文别名: But-3-enoxy-cyclopentyl-(3-methoxyprop-1-ynyl)-(2-methylhex-5-en-2-yloxy)silane；but-3-enoxy-cyclopentyl-(3-methoxyprop-1-ynyl)-(2-methylhex-5-en-2-yloxy)silane
• CAS: 873435-83-7
• 化学式: C₂₀H₃₄O₃Si
• 分子量: 350.574
• InChiKey: FAADANQHWKHEGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.92
• 重原子数：
  24
• 可旋转键数：
  12
• 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：

  But-3-enyloxy-cyclopentyl-(1,1-dimethyl-pent-4-enyloxy)-(3-methoxy-prop-1-ynyl)-silane 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 四丁基氟化铵 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 生成 (3E,5E)-5-Methoxymethyl-9-methyl-deca-3,5-diene-1,9-diol 、 (4E,6E)-5-Methoxymethyl-10-methyl-undeca-4,6-diene-1,10-diol
  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：

  Cyclopentyl-tris(3-methoxyprop-1-ynyl)silane 在 sodium hydride 作用下， 以 正己烷 为溶剂， 生成 But-3-enyloxy-cyclopentyl-(1,1-dimethyl-pent-4-enyloxy)-(3-methoxy-prop-1-ynyl)-silane
  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

文献信息

• Absence of the Thorpe–Ingold effect by gem-diphenyl groups in ring-closing enyne metathesis
  作者：Yi Jin Kim、Jonathan B. Grimm、Daesung Lee

  DOI：10.1016/j.tetlet.2007.09.063

  日期：2007.11

  ring-closing metathesis of alkynyl silaketals containing two different tethered olefins, the gem-dimethyl group showed the expected Thorpe-Ingold effect, thereby giving good level of group selectivity. Unexpectedly, however, the corresponding gem-diphenyl group did not show any Thorpe-Ingold effect for the ring closure reaction.

  在含有两种不同系链烯烃的炔基 silaketals 的串联闭环复分解中，gem-二甲基基团显示出预期的 Thorpe-Ingold 效应，从而提供了良好的基团选择性。然而，出乎意料的是，相应的 gem-二苯基基团在闭环反应中没有表现出任何 Thorpe-Ingold 效应。
• 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.