(+)-(R)-2-((R)-2-((4-methoxybenzyl)oxy)but-3-en-1-yl)-1,4-dioxaspiro[4.5]decane | 1440508-07-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+)-(R)-2-((R)-2-((4-methoxybenzyl)oxy)but-3-en-1-yl)-1,4-dioxaspiro[4.5]decane
• 英文别名: (3R)-3-[(2R)-2-[(4-methoxyphenyl)methoxy]but-3-enyl]-1,4-dioxaspiro[4.5]decane
• CAS: 1440508-07-5
• 化学式: C₂₀H₂₈O₄
• 分子量: 332.44
• InChiKey: CTAAQXZYILTNMV-PKOBYXMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+)-(R)-2-((R)-2-((4-methoxybenzyl)oxy)but-3-en-1-yl)-1,4-dioxaspiro[4.5]decane 在 咪唑 、 甲醇 、 [1,2-bis-(phenylsulfinyl)ethane]palladium(II) acetate 、 2,6-二甲基-2,5-环己二烯-1,4-二酮 、 氧气 、 potassium carbonate 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 78.0h， 生成 (+)-tert-butyl(((2R,6E,8E,10R)-10-((4-methoxybenzyl)oxy)-11-((R)-1,4-dioxaspiro[4.5]decan-2-yl)undeca-6,8-dien-2-yl)oxy)diphenylsilane
  参考文献：
  名称：

  Oxidative Heck Vinylation for the Synthesis of Complex Dienes and Polyenes

  摘要：

  We introduce an oxidative Heck reaction for selective complex diene and polyene formation. The reaction proceeds via oxidative Pd(II)/sulfoxide catalysis that retards palladium-hydride isomerizations which previously limited the Heck manifold's capacity for furnishing stereodefined conjugated dienes. Limiting quantities of nonactivated terminal olefins (1 equiv) and slight excesses of vinyl boronic esters (1.5 equiv) that feature diverse functionality can be used to furnish complex dienes and polyenes in good yields and excellent selectivities (generally E:Z = >20:1; internal:terminal = >20:1). Because this reaction only requires prior activation of a single vinylic carbon, improvements in efficiency are observed for synthetic sequences relative to ones featuring reactions that require activation of both coupling partners.

  DOI：

  10.1021/ja402891m
• 作为产物：
  描述：

  1,2-环氧基-5-己烯 在 [1,2-bis-(phenylsulfinyl)ethane]palladium(II) acetate 、 C₂₀H₂₀CoN₂O₂⁽²⁺⁾ 、 氧气 、 sodium hydride 、 对甲苯磺酸 、 N,N-二甲基甲酰胺 、 对苯醌 、 对硝基苯甲酸 作用下， 以 1,4-二氧六环 、 水 、 苯 为溶剂， 反应 48.0h， 生成 (+)-(R)-2-((R)-2-((4-methoxybenzyl)oxy)but-3-en-1-yl)-1,4-dioxaspiro[4.5]decane
  参考文献：
  名称：

  Oxidative Heck Vinylation for the Synthesis of Complex Dienes and Polyenes

  摘要：

  We introduce an oxidative Heck reaction for selective complex diene and polyene formation. The reaction proceeds via oxidative Pd(II)/sulfoxide catalysis that retards palladium-hydride isomerizations which previously limited the Heck manifold's capacity for furnishing stereodefined conjugated dienes. Limiting quantities of nonactivated terminal olefins (1 equiv) and slight excesses of vinyl boronic esters (1.5 equiv) that feature diverse functionality can be used to furnish complex dienes and polyenes in good yields and excellent selectivities (generally E:Z = >20:1; internal:terminal = >20:1). Because this reaction only requires prior activation of a single vinylic carbon, improvements in efficiency are observed for synthetic sequences relative to ones featuring reactions that require activation of both coupling partners.

  DOI：

  10.1021/ja402891m

文献信息

• Oxidative Heck Vinylation for the Synthesis of Complex Dienes and Polyenes
  作者：Jared H. Delcamp、Paul E. Gormisky、M. Christina White

  DOI：10.1021/ja402891m

  日期：2013.6.12

  We introduce an oxidative Heck reaction for selective complex diene and polyene formation. The reaction proceeds via oxidative Pd(II)/sulfoxide catalysis that retards palladium-hydride isomerizations which previously limited the Heck manifold's capacity for furnishing stereodefined conjugated dienes. Limiting quantities of nonactivated terminal olefins (1 equiv) and slight excesses of vinyl boronic esters (1.5 equiv) that feature diverse functionality can be used to furnish complex dienes and polyenes in good yields and excellent selectivities (generally E:Z = >20:1; internal:terminal = >20:1). Because this reaction only requires prior activation of a single vinylic carbon, improvements in efficiency are observed for synthetic sequences relative to ones featuring reactions that require activation of both coupling partners.