trans-5-Phenyl-2-penten-1-al diethyl acetal | 167482-59-9

• 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: trans-5-Phenyl-2-penten-1-al diethyl acetal
• 英文别名: 5-phenyl-2-pentenal diethyl acetal；[(E)-5,5-diethoxypent-3-enyl]benzene
• CAS: 167482-59-9
• 化学式: C₁₅H₂₂O₂
• 分子量: 234.338
• InChiKey: JFGBOJZBYOQGQB-UKTHLTGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  trans-5-Phenyl-2-penten-1-al diethyl acetal 在 diethylzinc 、 4-甲基苯磺酸吡啶 作用下， 以 正己烷 、 1,2-二氯乙烷 、 苯 为溶剂， 反应 48.0h， 生成 (2'S,3'aR,4S,7'S,7'aR)-2,2-dimethyl-2'-[(1S,2S)-2-(2-phenylethyl)cyclopropyl]-7'-[(4-phenylphenyl)methoxy]spiro[1,3-dioxolane-4,6'-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran]
  参考文献：
  名称：

  Asymmetric Cyclopropanation Using New Chiral Auxiliaries Derived from D-Fructose

  摘要：

  Acetals of alpha,beta-unsaturated aldehydes with 3-O-alkylated derivatives of 1,2-O-isopropylidene-beta-D-fructopyranose and 1,2-O-isopropylidene-beta-D-psicopyranose, which are readily available from D-fructose, were cyclopropanated with Et(2)Zn and CH2I2 with good diastereoselectivity. The effects of structure of the acetals on enantioselectivity were examined.

  DOI：

  10.1021/jo00108a018
• 作为产物：
  描述：

  (E)-5-phenyl-2-penten-1-ol 在 硝酸铵 、 pyridinium chlorochromate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 13.0h， 生成 trans-5-Phenyl-2-penten-1-al diethyl acetal
  参考文献：
  名称：

  Asymmetric Cyclopropanation Using New Chiral Auxiliaries Derived from D-Fructose

  摘要：

  Acetals of alpha,beta-unsaturated aldehydes with 3-O-alkylated derivatives of 1,2-O-isopropylidene-beta-D-fructopyranose and 1,2-O-isopropylidene-beta-D-psicopyranose, which are readily available from D-fructose, were cyclopropanated with Et(2)Zn and CH2I2 with good diastereoselectivity. The effects of structure of the acetals on enantioselectivity were examined.

  DOI：

  10.1021/jo00108a018

文献信息

• US4031140A
  申请人：——

  公开号：US4031140A

  公开（公告）日：1977-06-21
• US4036886A
  申请人：——

  公开号：US4036886A

  公开（公告）日：1977-07-19
• Asymmetric Cyclopropanation Using New Chiral Auxiliaries Derived from D-Fructose
  作者：Jahyo Kang、Geun Jho Lim、Suk Kyoon Yoon、Moohi Yoo Kim

  DOI：10.1021/jo00108a018

  日期：1995.2

  Acetals of alpha,beta-unsaturated aldehydes with 3-O-alkylated derivatives of 1,2-O-isopropylidene-beta-D-fructopyranose and 1,2-O-isopropylidene-beta-D-psicopyranose, which are readily available from D-fructose, were cyclopropanated with Et(2)Zn and CH2I2 with good diastereoselectivity. The effects of structure of the acetals on enantioselectivity were examined.