(5S,6S)-5,6-diphenyl-1,4-dioxan-2-one | 302842-83-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (5S,6S)-5,6-diphenyl-1,4-dioxan-2-one
• CAS: 302842-83-7
• 化学式: C₁₆H₁₄O₃
• 分子量: 254.285
• InChiKey: NMGREXCFUQYQEO-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5S,6S)-5,6-diphenyl-1,4-dioxan-2-one 在 氢气 、 三乙胺 、 双环己基(三氟甲烷磺酰氧基)硼烷 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (3S,5S,6S)-3-((S)-1-Methoxy-propyl)-5,6-diphenyl-[1,4]dioxan-2-one
  参考文献：
  名称：

  Anti-Selective Glycolate Aldol Additions with an Oxapyrone Boron Enolate

  摘要：

  GRAPHICSThe boron enolate of pyrone 2 undergoes asymmetric aldol reactions with aldehydes to give protected anti 1,2 diols 3. The pyrone is readily available from trans stilbene using asymmetric dihydroxylation. Yields for the aldol reaction range from 62 to 92% and the selectivities from 6:1 to >20:1 for the anti isomers, Protection and hydrogenolysis of the products can be used to remove the pyrone, giving differentially protected diol intermediates 12 that are amenable to multistep synthesis.

  DOI：

  10.1021/ol0002166
• 作为产物：
  描述：

  溴乙酸叔丁酯 、 (S,S)-(-)-氢化苯偶姻 在 二正丁基氧化锡 、 四丁基碘化铵 作用下， 以 苯 为溶剂， 反应 28.0h， 以67%的产率得到(5S,6S)-5,6-diphenyl-1,4-dioxan-2-one
  参考文献：
  名称：

  Anti-Selective Glycolate Aldol Additions with an Oxapyrone Boron Enolate

  摘要：

  GRAPHICSThe boron enolate of pyrone 2 undergoes asymmetric aldol reactions with aldehydes to give protected anti 1,2 diols 3. The pyrone is readily available from trans stilbene using asymmetric dihydroxylation. Yields for the aldol reaction range from 62 to 92% and the selectivities from 6:1 to >20:1 for the anti isomers, Protection and hydrogenolysis of the products can be used to remove the pyrone, giving differentially protected diol intermediates 12 that are amenable to multistep synthesis.

  DOI：

  10.1021/ol0002166

文献信息

• Synthesis of the Indolizidine Core of Virosinine A via a Microwave-Promoted Cascade Cyclization Involving Iminyl Radicals
  作者：Alexander Ramos、Elias D. Griffin、Kai-Hang Ho、Jatinder Singh、Spencer A. Jones、Steven N. Walter、Steven L. Castle

  DOI：10.1021/acs.orglett.3c03852

  日期：2024.1.19

  The indolizidine core of virosinine A was synthesized by means of a microwave-promoted cascade reaction featuring 5-exo-trig iminyl radical cyclization, thiyl radical elimination, and intramolecular imine alkylation. The resulting bicyclic iminium ion underwent stereoselective reduction by Red-Al to deliver the target compound. DFT calculations suggested that both the radical cyclization and thiyl

  Virosinine A 的吲哚里西啶核心是通过微波促进的级联反应合成的，该反应具有 5-外三亚胺基自由基环化、硫基自由基消除和分子内亚胺烷基化作用。所得的双环亚胺离子通过 Red-Al 进行立体选择性还原，得到目标化合物。 DFT 计算表明自由基环化和硫基自由基消除步骤在高反应温度下都是可逆的。
• US7173141B2
  申请人：——

  公开号：US7173141B2

  公开（公告）日：2007-02-06
• <i>Anti</i>-Selective Glycolate Aldol Additions with an Oxapyrone Boron Enolate
  作者：Merritt B. Andrus、B. B. V. Soma Sekhar、Erik L. Meredith、N. Kent Dalley

  DOI：10.1021/ol0002166

  日期：2000.9.1

  GRAPHICSThe boron enolate of pyrone 2 undergoes asymmetric aldol reactions with aldehydes to give protected anti 1,2 diols 3. The pyrone is readily available from trans stilbene using asymmetric dihydroxylation. Yields for the aldol reaction range from 62 to 92% and the selectivities from 6:1 to >20:1 for the anti isomers, Protection and hydrogenolysis of the products can be used to remove the pyrone, giving differentially protected diol intermediates 12 that are amenable to multistep synthesis.