(E)-4-hydroxy-6-phenylhex-5-enal diethyl acetal | 119702-47-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (E)-4-hydroxy-6-phenylhex-5-enal diethyl acetal
• 英文别名: (E)-6,6-diethoxy-1-phenylhex-1-en-3-ol
• CAS: 119702-47-5
• 化学式: C₁₆H₂₄O₃
• 分子量: 264.365
• InChiKey: MTBVECBPIPRAON-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-4-hydroxy-6-phenylhex-5-enal diethyl acetal 在 磷酸二苯酯 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 (2S,5S)-2-ethoxy-5-((E)-styryl)tetrahydrofuran 、 cis-2-ethoxy-5-((E)-styryl)tetrahydrofuran
  参考文献：
  名称：

  Kinetic Resolution of Homoaldols via Catalytic Asymmetric Transacetalization

  摘要：

  The highly enantioselective kinetic resolution of homoaldols via a transacetalization reaction has been achieved. A novel phosphoric acid, STRIP, based on a spirocyclic 1,1'-spirobiindane backbone was designed and identified as a superior catalyst for this transformation. Remarkably, both secondary and tertiary homoaldols gave equally excellent results.

  DOI：

  10.1021/ja108642s
• 作为产物：
  描述：

  反式肉桂醛 、 3-氯丙醛二乙醇缩醛 在 magnesium 、 1,2-二溴乙烷 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以81%的产率得到(E)-4-hydroxy-6-phenylhex-5-enal diethyl acetal
  参考文献：
  名称：

  Kinetic Resolution of Homoaldols via Catalytic Asymmetric Transacetalization

  摘要：

  The highly enantioselective kinetic resolution of homoaldols via a transacetalization reaction has been achieved. A novel phosphoric acid, STRIP, based on a spirocyclic 1,1'-spirobiindane backbone was designed and identified as a superior catalyst for this transformation. Remarkably, both secondary and tertiary homoaldols gave equally excellent results.

  DOI：

  10.1021/ja108642s

文献信息

• Barluenga, Jose; Fernandez, Jose R.; Rubiera, Covadonga, Journal of the Chemical Society. Perkin transactions I, 1988, p. 3113 - 3118
  作者：Barluenga, Jose、Fernandez, Jose R.、Rubiera, Covadonga、Yus, Miguel

  DOI：——

  日期：——
• BARLUENGA, JOSE;FERNANDEZ, JOSE R.;RUBIERA, COVADONGA;YUS, MIGUEL, J. CHEM. SOC. PERKIN TRANS. PT 1,(1988) N2, C. 3113-3117
  作者：BARLUENGA, JOSE、FERNANDEZ, JOSE R.、RUBIERA, COVADONGA、YUS, MIGUEL

  DOI：——

  日期：——
• Kinetic Resolution of Homoaldols via Catalytic Asymmetric Transacetalization
  作者：Ilija Čorić、Steffen Müller、Benjamin List

  DOI：10.1021/ja108642s

  日期：2010.12.15

  The highly enantioselective kinetic resolution of homoaldols via a transacetalization reaction has been achieved. A novel phosphoric acid, STRIP, based on a spirocyclic 1,1'-spirobiindane backbone was designed and identified as a superior catalyst for this transformation. Remarkably, both secondary and tertiary homoaldols gave equally excellent results.