(S)-4-((tert-butyldimethylsilyl)oxy)pent-1-en-3-one | 144193-95-3

• 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: (S)-4-((tert-butyldimethylsilyl)oxy)pent-1-en-3-one
• 英文别名: (S)-4-[(tert-butyldimethylsilyl)oxy]pent-1-en-3-one；(4S)-4-[tert-butyl(dimethyl)silyl]oxypent-1-en-3-one
• CAS: 144193-95-3
• 化学式: C₁₁H₂₂O₂Si
• 分子量: 214.38
• InChiKey: HXDUOOPPZPBNID-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.15
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-4-((tert-butyldimethylsilyl)oxy)pent-1-en-3-one 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 水 为溶剂， 以67%的产率得到(S)-4-hydroxy-1-penten-3-one
  参考文献：
  名称：

  Stereoselection in thermal asymmetric Diels-Alder reactions. Electronic vs. steric effects

  摘要：

  Experimental evidence was found for an electronic contribution favoring the cisoid conformation of alpha,beta-unsaturated carbonyl compounds in thermal Diels-Alder transition states.

  DOI：

  10.1021/jo00050a037
• 作为产物：
  描述：

  (s)-(-)-2-(叔丁基二甲基甲硅烷基氧基)丙酸乙酯 在 异丙基氯化镁 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成 (S)-4-((tert-butyldimethylsilyl)oxy)pent-1-en-3-one
  参考文献：
  名称：

  Total Synthesis of (+)-Phomopsolide C by Ring-Size Selective Ring-Closing Metathesis/Cross-Metathesis

  摘要：

  A new strategy for the synthesis of chiral 6-substituted 5,6-dihydro-5-hydroxypyran-2-ones by ring-size selective ring-closing metathesis (RCM) and its application to a short total synthesis of (+)-phomopsolide C are described. The key bond-forming reactions in this approach are a chemoselective cross-metathesis (CM) and RCM.

  DOI：

  10.1021/ol052332k

文献信息

• Desulfonylative Methenylation of β-Keto Sulfones
  作者：Ganesh Pandey、Janakiram Vaitla

  DOI：10.1021/acs.orglett.5b02455

  日期：2015.10.2

  A one-step strategy for the synthesis of alpha-methenyl ketones from beta-keto sufones is reported. Success of the methodology is elaborated for the synthesis of chromanones and isoflavanones in one-step.
• Stereocontrolled Synthesis of 1,3-Diols from Enones: Cooperative Lewis Base-Mediated Intramolecular Carbonyl Hydrosilylations
  作者：Casey Medina、Kyle P. Carter、Michael Miller、Timothy B. Clark、Gregory W. O’Neil

  DOI：10.1021/jo401293a

  日期：2013.9.20

  A streamlined synthesis of beta-hydroxy ketone substrates has been developed to further investigate a recently discovered cooperative Lewis base-mediated intramolecular carbonyl hydrosilylation reaction. The synthesis features an enone beta-borylation/oxidation sequence that has proven to be quite general and high-yielding. This has allowed for additional investigations into the diastereoselectivity of the hydrosilylation reaction through the preparation of important polyketide fragments.
• Total Synthesis of (+)-Phomopsolide C by Ring-Size Selective Ring-Closing Metathesis/Cross-Metathesis
  作者：Simon Michaelis、Siegfried Blechert

  DOI：10.1021/ol052332k

  日期：2005.11.1

  A new strategy for the synthesis of chiral 6-substituted 5,6-dihydro-5-hydroxypyran-2-ones by ring-size selective ring-closing metathesis (RCM) and its application to a short total synthesis of (+)-phomopsolide C are described. The key bond-forming reactions in this approach are a chemoselective cross-metathesis (CM) and RCM.
• Stereoselection in thermal asymmetric Diels-Alder reactions. Electronic vs. steric effects
  作者：Blanda Stammen、Ulrich Berlage、Richard Kindermann、William S. Sheldrick、Peter Welzel、Wolfgang R. Roth、Manfred Kaiser、Barbara Guenther

  DOI：10.1021/jo00050a037

  日期：1992.11

  Experimental evidence was found for an electronic contribution favoring the cisoid conformation of alpha,beta-unsaturated carbonyl compounds in thermal Diels-Alder transition states.