2-(3-methylenepent-4-en-1-yl)-1,3-dioxolane | 23985-10-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧戊环
• 英文名称: 2-(3-methylenepent-4-en-1-yl)-1,3-dioxolane
• 英文别名: 3-Methylen-6,6-ethylendioxy-hexen-(1)；2-(3-methylene-pent-4-enyl)-[1,3]dioxolane；2-(3-Methylidenepent-4-enyl)-1,3-dioxolane；2-(3-methylidenepent-4-enyl)-1,3-dioxolane
• CAS: 23985-10-6
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: GERIJPKRGMPBMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  2-(3-methylenepent-4-en-1-yl)-1,3-dioxolane 在 lithium aluminium tetrahydride 、 对甲苯磺酸 作用下， 以 水 、 丙酮 、 苯 为溶剂， 反应 2.5h， 生成 2-甲基-6-亚甲基-辛-2,7-二烯-1-醇
  参考文献：
  名称：

  Vig,O.P. et al., Journal of the Indian Chemical Society, 1975, vol. 52, p. 161 - 163

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(2-溴乙基)-1,3-二恶烷 、 1,4-二溴-2-丁烯 在 碘 、 magnesium 、 copper(l) iodide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 以40 %的产率得到2-(3-methylenepent-4-en-1-yl)-1,3-dioxolane
  参考文献：
  名称：

  Hydrogen Source Tuned Regiodivergent Asymmetric Hydroalkylations of 2‐Substituted 1,3‐Dienes with Aldehydes by Cobalt‐Catalysis

  摘要：

  Catalytic methods allowing for the reliable prediction and control of diverse regioselectivity along with the control of enantioselectivity to access different regio‐ and enantiomers by switching the least reaction parameters are one of the most attractive ways in organic synthesis, which provide access to diverse enantioenriched architectures from identical starting materials. Herein, a Co‐catalyzed regiodivergent and enantioselective reductive hydroalkylation of 1,3‐dienes with aldehydes have been achieved, furnishing different enantioenriched homoallylic alcohol architectures in good levels of enantioselectivity. The reaction features the switch of regioselectivity tuned by the selection of proton source. The use of an acid as proton source provided asymmetric 1,2‐hydroalkylation products under reductive conditions, yet asymmetric 4,3‐hydroalkylation products were obtained with silane as hydride source. This catalytic protocol allows for the access of homoallylic alcohols with two continuous saturated carbon centers in good levels of regio‐, diastereo‐, and enantioselectivity.

  DOI：

  10.1002/anie.202403073

文献信息

• JPS63275578A
  申请人：——

  公开号：JPS63275578A

  公开（公告）日：1988-11-14
• Vig,O.P. et al., Journal of the Indian Chemical Society, 1975, vol. 52, p. 161 - 163
  作者：Vig,O.P. et al.

  DOI：——

  日期：——
• Hydrogen Source Tuned Regiodivergent Asymmetric Hydroalkylations of 2‐Substituted 1,3‐Dienes with Aldehydes by Cobalt‐Catalysis
  作者：Xian-Wang Zeng、Jia-Ni Lin、Wei Shu

  DOI：10.1002/anie.202403073

  日期：——

  Catalytic methods allowing for the reliable prediction and control of diverse regioselectivity along with the control of enantioselectivity to access different regio‐ and enantiomers by switching the least reaction parameters are one of the most attractive ways in organic synthesis, which provide access to diverse enantioenriched architectures from identical starting materials. Herein, a Co‐catalyzed regiodivergent and enantioselective reductive hydroalkylation of 1,3‐dienes with aldehydes have been achieved, furnishing different enantioenriched homoallylic alcohol architectures in good levels of enantioselectivity. The reaction features the switch of regioselectivity tuned by the selection of proton source. The use of an acid as proton source provided asymmetric 1,2‐hydroalkylation products under reductive conditions, yet asymmetric 4,3‐hydroalkylation products were obtained with silane as hydride source. This catalytic protocol allows for the access of homoallylic alcohols with two continuous saturated carbon centers in good levels of regio‐, diastereo‐, and enantioselectivity.