4-(4-Chloro-tetrahydro-pyran-2-yl)-butan-1-ol | 92827-00-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 4-(4-Chloro-tetrahydro-pyran-2-yl)-butan-1-ol
• 英文别名: 4-(4-chlorooxan-2-yl)butan-1-ol
• CAS: 92827-00-4
• 化学式: C₉H₁₇ClO₂
• 分子量: 192.686
• InChiKey: HHJPWAGQCZTEGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(4-Chloro-tetrahydro-pyran-2-yl)-butan-1-ol 在 sodium tetrahydroborate 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 六甲基磷酰三胺 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 4-(Oxan-2-YL)butanal
  参考文献：
  名称：

  Room Temperature Hydroalkylation of Electron-Deficient Olefins:  sp³ C−H Functionalization via a Lewis Acid-Catalyzed Intramolecular Redox Event

  摘要：

  A practical method for the intramolecular hydroalkylation of electron-deficient olefins has been developed. The direct transformation of benzylic, tertiary, and sterically hindered secondary sp3 C-H bonds into C-C bonds under the action of a catalytic amount of a variety of Lewis acids is described. The mechanism of these transformations is proposed to involve a tandem hydride transfer/cyclization sequence.

  DOI：

  10.1021/ja053337f
• 作为产物：
  描述：

  4-(四氢吡喃-2-基氧基)-1-丁烯 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 30.0h， 以86%的产率得到4-(4-Chloro-tetrahydro-pyran-2-yl)-butan-1-ol
  参考文献：
  名称：

  Room Temperature Hydroalkylation of Electron-Deficient Olefins:  sp³ C−H Functionalization via a Lewis Acid-Catalyzed Intramolecular Redox Event

  摘要：

  A practical method for the intramolecular hydroalkylation of electron-deficient olefins has been developed. The direct transformation of benzylic, tertiary, and sterically hindered secondary sp3 C-H bonds into C-C bonds under the action of a catalytic amount of a variety of Lewis acids is described. The mechanism of these transformations is proposed to involve a tandem hydride transfer/cyclization sequence.

  DOI：

  10.1021/ja053337f

文献信息

• The synthesis of 4-halotetrahydropyrans and 4-halo-5,6-dihydro-2H-pyrans via the lewis acid promoted cyclization of acetals of homoallylic and homopropargylic alcohols
  作者：W.H. Bunnelle、D.W. Seamon、D.L. Mohler、T.F. Ball、D.W. Thompson

  DOI：10.1016/s0040-4039(01)81254-5

  日期：1984.1
• BUNNELLE, W. H.;SEAMON, D. W.;MOHLER, D. L.;BALL, T. F.;THOMPSON, D. W., TETRAHEDRON LETT., 1984, 25, N 25, 2653-2654
  作者：BUNNELLE, W. H.、SEAMON, D. W.、MOHLER, D. L.、BALL, T. F.、THOMPSON, D. W.

  DOI：——

  日期：——
• Room Temperature Hydroalkylation of Electron-Deficient Olefins:  sp³ C−H Functionalization via a Lewis Acid-Catalyzed Intramolecular Redox Event
  作者：Stefan J. Pastine、Kevin M. McQuaid、Dalibor Sames

  DOI：10.1021/ja053337f

  日期：2005.9.1

  A practical method for the intramolecular hydroalkylation of electron-deficient olefins has been developed. The direct transformation of benzylic, tertiary, and sterically hindered secondary sp3 C-H bonds into C-C bonds under the action of a catalytic amount of a variety of Lewis acids is described. The mechanism of these transformations is proposed to involve a tandem hydride transfer/cyclization sequence.