(E)-But-2-enoic acid (3aR,5R,6S,6aR)-5-benzyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester | 137585-71-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-But-2-enoic acid (3aR,5R,6S,6aR)-5-benzyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester
• CAS: 137585-71-8
• 化学式: C₁₈H₂₂O₅
• 分子量: 318.37
• InChiKey: OQGIFGBBQRDVAF-MDKFXEQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.59
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  HEPTYLMAGNESIUM BROMIDE 、 (E)-But-2-enoic acid (3aR,5R,6S,6aR)-5-benzyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 在 copper(I) bromide dimethylsulfide complex 作用下， 生成 3-Methyl-decanoic acid (3aR,5R,6S,6aR)-5-benzyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester
  参考文献：
  名称：

  5-Deoxy-5-alkyl-1,2-O-isopropylidene-α-D-xylofuranoses as chiral auxiliaries in asymmetric 1,4-addition reaction

  摘要：

  Two deoxy-sugar based chiral auxiliaries (2 and 5) have been prepared. Their alpha,beta-unsaturated esters were treated with different cuprate reagents to give the 1,4-addition adducts in good chemical yield and good diastereoselectivity.

  DOI：

  10.1016/s0957-4166(00)82200-4
• 作为产物：
  描述：

  2,2-dimethyl-5-phenylmethyl-(3aR,5R,6aR)-perhydrofuro[2,3-d][1,3]-dioxol-(6S)-ol 、 2-丁烯酰氯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到(E)-But-2-enoic acid (3aR,5R,6S,6aR)-5-benzyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester
  参考文献：
  名称：

  5-Deoxy-5-alkyl-1,2-O-isopropylidene-α-D-xylofuranoses as chiral auxiliaries in asymmetric 1,4-addition reaction

  摘要：

  Two deoxy-sugar based chiral auxiliaries (2 and 5) have been prepared. Their alpha,beta-unsaturated esters were treated with different cuprate reagents to give the 1,4-addition adducts in good chemical yield and good diastereoselectivity.

  DOI：

  10.1016/s0957-4166(00)82200-4