(S)-2-(benzyloxymethyl)-2,5-dihydrofuran | 141522-07-8

• 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: (S)-2-(benzyloxymethyl)-2,5-dihydrofuran
• 英文别名: (S)-2-benzyloxymethyl-2,5-dihydrofuran；(2S)-2-(phenylmethoxymethyl)-2,5-dihydrofuran
• CAS: 141522-07-8
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: KXUHHBQJWZFGJN-LBPRGKRZSA-N

物化性质

• 沸点：
  290.6±35.0 °C(Predicted)
• 密度：
  1.070±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-2-(benzyloxymethyl)-2,5-dihydrofuran 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以78%的产率得到2-benzyloxymethyl-3,4-epoxy-tetrahydrofuran
  参考文献：
  名称：

  Synthesis of amino-1,4-anhydro-d-pentitols and amino-1,5-anhydro-d-hexitols with the arabino configuration from (R)-glycidol

  摘要：

  2-Amino-1,4-anhydro-pentitol and 3-amino-1,5-anhydro-4-deoxy-hexitol with the arabino configuration were synthesised from (R)-glycidol using a metathesis reaction as the key step. The dihydrofuran or dihydropyran products obtained after the metathesis reaction were subjected to epoxidation, epoxide opening with azide anion and finally azide reduction. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00325-2
• 作为产物：
  描述：

  (S)-苄氧甲基环氧乙烷 在 Grubbs catalyst first generation 、 正丁基锂 、 乙烯 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 8.5h， 生成 (S)-2-(benzyloxymethyl)-2,5-dihydrofuran
  参考文献：
  名称：

  Synthesis of amino-1,4-anhydro-d-pentitols and amino-1,5-anhydro-d-hexitols with the arabino configuration from (R)-glycidol

  摘要：

  2-Amino-1,4-anhydro-pentitol and 3-amino-1,5-anhydro-4-deoxy-hexitol with the arabino configuration were synthesised from (R)-glycidol using a metathesis reaction as the key step. The dihydrofuran or dihydropyran products obtained after the metathesis reaction were subjected to epoxidation, epoxide opening with azide anion and finally azide reduction. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00325-2

文献信息

• Stereoselective Ring Expansion of Vinyl Oxiranes: Mechanistic Insights and Natural Product Total Synthesis
  作者：Matthew Brichacek、Lindsay A. Batory、Jon T. Njardarson

  DOI：10.1002/anie.200906830

  日期：2010.2.22

  applicable, catalytic, and stereoselective vinyl oxirane ring expansion is described (see scheme; hfacac=hexafluoroacetylacetonate). The stereoselectivity was influenced by several reaction parameters, and kinetic studies support a mechanistic proposal involving the in situ formation of a more reactive catalytic species. This ring‐expansion reaction has been employed in the asymmetric total synthesis

  真是（紧张）的解脱！描述了第一个广泛适用的，催化的和立体选择性的乙烯基环氧乙烷环扩环（参见方案； hfacac =六氟乙酰丙酮酸酯）。立体选择性受几个反应参数的影响，动力学研究支持了一种机制性的提议，涉及原位形成更具反应性的催化物质。该扩环反应已用于（+）-邻苯二酚二醇的不对称全合成中。
• Catalytic Asymmetric Ring‐Opening Reactions of Unstrained Heterocycles Using Cobalt Vinylidenes
  作者：Vibha V. Kanale、Christopher Uyeda

  DOI：10.1002/anie.202309681

  日期：2023.10.16

  Cobalt catalysts promote enantioselective ring-opening reactions of unstrained heterocycles by the reductive addition of 1,1-dichloroalkenes. The products are acyclic homoallylic alcohols containing a vinylzinc motif, which can be further functionalized with an electrophile. Mechanistic studies suggest that ring-opening occurs by an outer-sphere β-O elimination assisted by a Zn(II) Lewis acid.

  钴催化剂通过还原添加 1,1-二氯烯烃来促进未应变杂环的对映选择性开环反应。这些产品是含有乙烯基锌基序的无环同烯丙醇，可以用亲电试剂进一步官能化。机理研究表明，开环是通过 Zn（II） 路易斯酸辅助的外球 β-O 消除发生的。