3-(di-tert-butyl-fluoro-silaniloxy)-5-phenyl-pentan-1-ol | 442636-01-3

• 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: 3-(di-tert-butyl-fluoro-silaniloxy)-5-phenyl-pentan-1-ol
• 英文别名: 3-[Ditert-butyl(fluoro)silyl]oxy-5-phenylpentan-1-ol
• CAS: 442636-01-3
• 化学式: C₁₉H₃₃FO₂Si
• 分子量: 340.554
• InChiKey: DCEZEPIJRGMHPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(di-tert-butyl-fluoro-silaniloxy)-5-phenyl-pentan-1-ol 在 sodium hydroxide 、 三氯化硼 作用下， 以 四氢呋喃 、 正庚烷 、 氯仿 、 水 为溶剂， 反应 25.0h， 生成 3-(Di-tert-butyl-chloro-silanyloxy)-5-phenyl-pentan-1-ol
  参考文献：
  名称：

  The Regioselective Mono-deprotection of 1,3-Dioxa-2,2-(di-tert-butyl)-2-silacyclohexanes with BF₃·SMe₂

  摘要：

  The selective mono-deprotection of di-tert-butylsilylene ethers prepared from substituted 1,3-pentanediols and 2,4-hexanediols has been achieved with BF3.SMe2. The reaction conditions are compatible with esters, allyl ethers, and TIPS ethers. The resulting di-tert-butylfluorosilyl ethers are stable to various conditions including low pH aqueous solutions and silica gel chromatography; the di-tert-butylfluorosilyl ethers are readily cleaved with HF-pyridine. Substrate stereochemistry and conformation influences the efficiency of the deprotection, while the deprotection regiochemistry is consistent with coordination of boron to the sterically more accessible oxygen prior to intramolecular delivery of fluoride.

  DOI：

  10.1021/jo025624x
• 作为产物：
  描述：

  5-phenylpentane-1,3-diol 在 3 A molecular sieve 三氟二甲基硫醚络合物 、 potassium acetate 、 烯丙基三甲基硅烷 作用下， 以 四氢呋喃 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.17h， 生成 3-(di-tert-butyl-fluoro-silaniloxy)-5-phenyl-pentan-1-ol
  参考文献：
  名称：

  The Regioselective Mono-deprotection of 1,3-Dioxa-2,2-(di-tert-butyl)-2-silacyclohexanes with BF₃·SMe₂

  摘要：

  The selective mono-deprotection of di-tert-butylsilylene ethers prepared from substituted 1,3-pentanediols and 2,4-hexanediols has been achieved with BF3.SMe2. The reaction conditions are compatible with esters, allyl ethers, and TIPS ethers. The resulting di-tert-butylfluorosilyl ethers are stable to various conditions including low pH aqueous solutions and silica gel chromatography; the di-tert-butylfluorosilyl ethers are readily cleaved with HF-pyridine. Substrate stereochemistry and conformation influences the efficiency of the deprotection, while the deprotection regiochemistry is consistent with coordination of boron to the sterically more accessible oxygen prior to intramolecular delivery of fluoride.

  DOI：

  10.1021/jo025624x

文献信息

• The Regioselective Mono-deprotection of 1,3-Dioxa-2,2-(di-<i>tert</i>-butyl)-2-silacyclohexanes with BF₃·SMe₂
  作者：Ming Yu、Brian L. Pagenkopf

  DOI：10.1021/jo025624x

  日期：2002.6.1

  The selective mono-deprotection of di-tert-butylsilylene ethers prepared from substituted 1,3-pentanediols and 2,4-hexanediols has been achieved with BF3.SMe2. The reaction conditions are compatible with esters, allyl ethers, and TIPS ethers. The resulting di-tert-butylfluorosilyl ethers are stable to various conditions including low pH aqueous solutions and silica gel chromatography; the di-tert-butylfluorosilyl ethers are readily cleaved with HF-pyridine. Substrate stereochemistry and conformation influences the efficiency of the deprotection, while the deprotection regiochemistry is consistent with coordination of boron to the sterically more accessible oxygen prior to intramolecular delivery of fluoride.