3,3-Difluoroheptadec-1-en-4-ol | 1310740-05-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: 3,3-Difluoroheptadec-1-en-4-ol
• CAS: 1310740-05-6
• 化学式: C₁₇H₃₂F₂O
• 分子量: 290.437
• InChiKey: NLVHDVPEWGHKMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  20
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,3-Difluoroheptadec-1-en-4-ol 在 sodium azide 、 二甲基氯化铝 作用下， 以 正己烷 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 1.83h， 生成 (Z)-1-azido-3-fluoroheptadec-2-en-4-ol
  参考文献：
  名称：

  Synthesis of (Z)-fluoroallyl azides through aluminium-mediated defluorinative functionalization reactions

  摘要：

  The reaction of difluorohomoallyl alcohols with Me2AlCl in CH2Cl2 selectively gave (Z)-fluoroallyl chlorides via S(N)2' type defluorinative chlorination. These chlorides were easily converted to the corresponding (Z)-fluoroallyl azides by the sequential nucleophilic azidation reaction using NaN3. Direct defluorinative azidation of the difluorohomoallyl alcohols was also achieved by treating with Me3SiN3 in the presence of Al(Oi-Pr)(3). Fluoroallyl azides thus obtained successfully applied to the Huisgen. 1,3-dipolar cycloaddition chemistry. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.12.128

文献信息

• Copper-free defluorinative alkylation of allylic difluorides through Lewis acid-mediated C–F bond activation
  作者：Hikaru Yanai、Haruna Okada、Azusa Sato、Midori Okada、Takeo Taguchi

  DOI：10.1016/j.tetlet.2011.03.148

  日期：2011.6

  The reactions of difluorohomoallyl alcohols with trialkylaluminiums smoothly proceeded in CH2Cl2 at room temperature to give (Z)-fluoro-olefin products in excellent yields. On the basis of this chemistry, fluoro-olefinic dipeptide isostere of norvalinyl glycine was synthesized in stereoselective manner. (C) 2011 Elsevier Ltd. All rights reserved.