6-(((tert-butyldimethylsilyl)oxy)methyl)-6-hydroxy-2-(pent-4-en-1-yl)-2H-pyran-3(6H)-one | 1331831-35-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 6-(((tert-butyldimethylsilyl)oxy)methyl)-6-hydroxy-2-(pent-4-en-1-yl)-2H-pyran-3(6H)-one
• CAS: 1331831-35-6
• 化学式: C₁₇H₃₀O₄Si
• 分子量: 326.508
• InChiKey: ZKXSSUVLJPZRQS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.58
• 重原子数：
  22.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  6-(((tert-butyldimethylsilyl)oxy)methyl)-6-hydroxy-2-(pent-4-en-1-yl)-2H-pyran-3(6H)-one 在 4-二甲氨基吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Dual Catalysis in Enantioselective Oxidopyrylium-Based [5 + 2] Cycloadditions

  摘要：

  A new method for effecting catalytic enantioselective intramolecular [5 + 2] cycloadditions based on oxidopyrylium intermediates is reported. The dual catalyst system consists of a chiral primary aminothiourea and a second achiral thiourea. Experimental evidence points to a new type of cooperative catalysis with each species being necessary to generate a reactive pyrylium ion pair that undergoes subsequent cycloaddition with high enantioselectivity.

  DOI：

  10.1021/ja206997e
• 作为产物：
  描述：

  magnesium,pent-1-ene,bromide 在 叔丁基过氧化氢 、 bis(acetylacetonate)oxovanadium 作用下， 以 四氢呋喃 、 十二烷 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 6-(((tert-butyldimethylsilyl)oxy)methyl)-6-hydroxy-2-(pent-4-en-1-yl)-2H-pyran-3(6H)-one
  参考文献：
  名称：

  Dual Catalysis in Enantioselective Oxidopyrylium-Based [5 + 2] Cycloadditions

  摘要：

  A new method for effecting catalytic enantioselective intramolecular [5 + 2] cycloadditions based on oxidopyrylium intermediates is reported. The dual catalyst system consists of a chiral primary aminothiourea and a second achiral thiourea. Experimental evidence points to a new type of cooperative catalysis with each species being necessary to generate a reactive pyrylium ion pair that undergoes subsequent cycloaddition with high enantioselectivity.

  DOI：

  10.1021/ja206997e

文献信息

• Oxidopyrylium-Alkene [5 + 2] Cycloaddition Conjugate Addition Cascade (C³) Sequences: Scope, Limitation, and Computational Investigations
  作者：Riley H. Kaufman、Chunyin M. Law、Justin A. Simanis、Erica L. Woodall、Christian R. Zwick、Henry B. Wedler、Paul Wendelboe、Christopher G. Hamaker、John R. Goodell、Dean J. Tantillo、T. Andrew Mitchell

  DOI：10.1021/acs.joc.8b01322

  日期：2018.9.7

  Oxidopyrylium-alkene [5 + 2] cycloaddition conjugate addition cascade (C3) sequences are described. Intramolecular cycloadditions involving terminal alkenes, enals, and enones were investigated. Substrates with tethers of varying lengths delivered five- and six-membered carbocycles and heterocycles thus demonstrating the scope and limitation of the cycloaddition–conjugate addition cascade. Several

  描述了氧吡啶鎓-烯烃[5 + 2]环加成共轭加成级联（C 3）序列。研究了涉及末端烯烃，烯醛和烯酮的分子内环加成反应。带有不同长度束缚的底物传递了五元和六元碳环和杂环，从而证明了环加成-共轭加成级联反应的范围和局限性。若干实验和理论计算为提出的机制途径提供了证据。