(+)-(3S,4S)-5-(苄氧基)-3,4-二甲基戊醛 | 1054486-95-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (+)-(3S,4S)-5-(苄氧基)-3,4-二甲基戊醛
• 英文名称: (+)-(3S,4S)-5-(benzyloxy)-3,4-dimethylpentanal
• 英文别名: (3S,4S)-3,4-dimethyl-5-phenylmethoxypentanal
• CAS: 1054486-95-1
• 化学式: C₁₄H₂₀O₂
• 分子量: 220.312
• InChiKey: GGGBMCAZWDVLIM-QWHCGFSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+)-(3S,4S)-5-(苄氧基)-3,4-二甲基戊醛 、 碘化异丙基三苯鏻 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 以90%的产率得到(+)-benzyl (2S,3S)-2,3,6-trimethyl-5-heptenyl ether
  参考文献：
  名称：

  Catalytic Enantioselective Synthesis of Vicinal Dialkyl Arrays

  摘要：

  With a consecutive "asymmetric allylic alkylation (AAA)/cross-metathesis (CM)/conjugate addition (CA)" protocol it is possible to synthesize either stereoisomer of compounds containing a vicinal dialkyl array with excellent stereoselectivity. The versatility of this protocol in natural product synthesis is demonstrated in the preparation of the ant pheromones faranal and lasiol.

  DOI：

  10.1021/jo8010649
• 作为产物：
  描述：

  (+)-S-ethyl (3S,4S)-5-(benzyloxy)-3,4-dimethylpentanethioate 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以96%的产率得到(+)-(3S,4S)-5-(苄氧基)-3,4-二甲基戊醛
  参考文献：
  名称：

  Catalytic Enantioselective Synthesis of Vicinal Dialkyl Arrays

  摘要：

  With a consecutive "asymmetric allylic alkylation (AAA)/cross-metathesis (CM)/conjugate addition (CA)" protocol it is possible to synthesize either stereoisomer of compounds containing a vicinal dialkyl array with excellent stereoselectivity. The versatility of this protocol in natural product synthesis is demonstrated in the preparation of the ant pheromones faranal and lasiol.

  DOI：

  10.1021/jo8010649

文献信息

• Catalytic Enantioselective Synthesis of Vicinal Dialkyl Arrays
  作者：Anthoni W. van Zijl、Wiktor Szymanski、Ferrnando López、Adriaan J. Minnaard、Ben L. Feringa

  DOI：10.1021/jo8010649

  日期：2008.9.19

  With a consecutive "asymmetric allylic alkylation (AAA)/cross-metathesis (CM)/conjugate addition (CA)" protocol it is possible to synthesize either stereoisomer of compounds containing a vicinal dialkyl array with excellent stereoselectivity. The versatility of this protocol in natural product synthesis is demonstrated in the preparation of the ant pheromones faranal and lasiol.