Levulinaldehyde dimethyl acetal | 1415336-30-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Levulinaldehyde dimethyl acetal
• 英文别名: 4,4-dimethoxypentanal
• CAS: 1415336-30-9
• 化学式: C₇H₁₄O₃
• 分子量: 146.186
• InChiKey: MYJRBYOSWDFTJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  Levulinaldehyde dimethyl acetal 在 咪唑 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 0.08h， 生成 C₂₉H₄₂O₄Si
  参考文献：
  名称：

  Lewis Acid Catalyzed Intramolecular Condensation of Ynol Ether-Acetals. Synthesis of Alkoxycycloalkene Carboxylates

  摘要：

  Treatment of ynol ether-tethered dialkyl acetals with catalytic quantities of scandium triflate in CH3CN gives rise to five-, six-, and seven-membered alkoxycycloalkene carboxylates in good to excellent yields. Tri- and tetrasubstituted carbocyclic and heterocyclic alkenes may be formed by this method, and the products obtained may serve as useful intermediates for natural product synthesis.

  DOI：

  10.1021/ol303026v
• 作为产物：
  描述：

  C₇H₁₄O₄ 在 lithium aluminium tetrahydride 、 草酰氯 、 二甲基亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.25h， 生成 Levulinaldehyde dimethyl acetal
  参考文献：
  名称：

  Lewis Acid Catalyzed Intramolecular Condensation of Ynol Ether-Acetals. Synthesis of Alkoxycycloalkene Carboxylates

  摘要：

  Treatment of ynol ether-tethered dialkyl acetals with catalytic quantities of scandium triflate in CH3CN gives rise to five-, six-, and seven-membered alkoxycycloalkene carboxylates in good to excellent yields. Tri- and tetrasubstituted carbocyclic and heterocyclic alkenes may be formed by this method, and the products obtained may serve as useful intermediates for natural product synthesis.

  DOI：

  10.1021/ol303026v

文献信息

• A Single-Flask Synthesis of Morita–Baylis–Hillman Adducts from Ethoxyacetylene and Carbonyl Compounds: Synthesis of Subamolides D and E
  作者：Kevin Ng、Thomas G. Minehan

  DOI：10.1021/acs.orglett.6b01772

  日期：2016.8.19

  keto/aldehyde acetals (X = OMe) followed by the addition of a Lewis acid leads to five-, six-, and seven-membered hydroxycycloalkene carboxyates. The utility of this method is demonstrated in the synthesis of the α-alkylidene lactone natural products subamolide D and E.

  用醛和/或酮（2和4）和BF 3 ·OEt 2顺序处理（乙氧基乙炔基）锂可产生β-羟基烯酸酯5，总收率良好。类似地，1（M = Li）和二羰基化合物6（X = O）或酮/醛缩醛（X = OMe）的组合，然后添加路易斯酸，会生成五元，六元和七元羟基环烯羧酸盐。该方法的实用性在合成α-亚烷基内酯天然产物亚磺酰胺D和E中得到了证明。
• Lewis Acid Catalyzed Intramolecular Condensation of Ynol Ether-Acetals. Synthesis of Alkoxycycloalkene Carboxylates
  作者：Vincent Tran、Thomas G. Minehan

  DOI：10.1021/ol303026v

  日期：2012.12.7

  Treatment of ynol ether-tethered dialkyl acetals with catalytic quantities of scandium triflate in CH3CN gives rise to five-, six-, and seven-membered alkoxycycloalkene carboxylates in good to excellent yields. Tri- and tetrasubstituted carbocyclic and heterocyclic alkenes may be formed by this method, and the products obtained may serve as useful intermediates for natural product synthesis.