Methyl 4-(2-fluorophenyl)-4-hydroxybutanoate | 1249051-23-7

• 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: Methyl 4-(2-fluorophenyl)-4-hydroxybutanoate
• CAS: 1249051-23-7
• 化学式: C₁₁H₁₃FO₃
• 分子量: 212.221
• InChiKey: FXTLFRCVJDOXJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Methyl 4-(2-fluorophenyl)-4-hydroxybutanoate 在 zinc(II) chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 以72%的产率得到2-(2-Fluorophenyl)oxolane
  参考文献：
  名称：

  Quick Installation of a 1,4-Difunctionality via Regioselective Nickel-Catalyzed Reductive Coupling of Ynoates and Aldehydes

  摘要：

  The development of efficient methods for the synthesis of molecules with 1,4-difunctionalities has been a dire need of the synthetic community. In this work, intermolecular reductive coupling of ynoates and aldehydes (in the presence of a silane) has been accomplished for the first time using catalytic amounts of Ni(COD)(2), an N-heterocyclic carbene ligand, and PPh3. High regioselectivity has been demonstrated for the multicomponent coupling reactions, and more than a dozen invaluable silyl-protected gamma-hydrox-alpha,beta-enoates have been synthesized. This methodology provides a quick entry to many other 1,4-difunctional compounds and oxygen-containing five-membered rings. The intermediacy of metallacycles in the catalytic process has been established by deuterium-labeling experiments.

  DOI：

  10.1021/jo301790q
• 作为产物：
  描述：

  methyl 4-(2-fluorophenyl)-4-oxobutanoate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以95%的产率得到Methyl 4-(2-fluorophenyl)-4-hydroxybutanoate
  参考文献：
  名称：

  Quick Installation of a 1,4-Difunctionality via Regioselective Nickel-Catalyzed Reductive Coupling of Ynoates and Aldehydes

  摘要：

  The development of efficient methods for the synthesis of molecules with 1,4-difunctionalities has been a dire need of the synthetic community. In this work, intermolecular reductive coupling of ynoates and aldehydes (in the presence of a silane) has been accomplished for the first time using catalytic amounts of Ni(COD)(2), an N-heterocyclic carbene ligand, and PPh3. High regioselectivity has been demonstrated for the multicomponent coupling reactions, and more than a dozen invaluable silyl-protected gamma-hydrox-alpha,beta-enoates have been synthesized. This methodology provides a quick entry to many other 1,4-difunctional compounds and oxygen-containing five-membered rings. The intermediacy of metallacycles in the catalytic process has been established by deuterium-labeling experiments.

  DOI：

  10.1021/jo301790q

文献信息

• Quick Installation of a 1,4-Difunctionality via Regioselective Nickel-Catalyzed Reductive Coupling of Ynoates and Aldehydes
  作者：Sanjeewa K. Rodrigo、Hairong Guan

  DOI：10.1021/jo301790q

  日期：2012.9.21

  The development of efficient methods for the synthesis of molecules with 1,4-difunctionalities has been a dire need of the synthetic community. In this work, intermolecular reductive coupling of ynoates and aldehydes (in the presence of a silane) has been accomplished for the first time using catalytic amounts of Ni(COD)(2), an N-heterocyclic carbene ligand, and PPh3. High regioselectivity has been demonstrated for the multicomponent coupling reactions, and more than a dozen invaluable silyl-protected gamma-hydrox-alpha,beta-enoates have been synthesized. This methodology provides a quick entry to many other 1,4-difunctional compounds and oxygen-containing five-membered rings. The intermediacy of metallacycles in the catalytic process has been established by deuterium-labeling experiments.