2-bromo-4-tert-butyl-6-(hydroxymethyl)phenol | 2599-63-5

• 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: 2-bromo-4-tert-butyl-6-(hydroxymethyl)phenol
• 英文别名: 2-bromo-4-tert-butyl-6-hydroxymethyl phenol；3-bromo-5-tert-butylsalicyl alcohol；6-bromo-4-tert-butylsalicyl alcohol
• CAS: 2599-63-5
• 化学式: C₁₁H₁₅BrO₂
• 分子量: 259.143
• InChiKey: IHSJXPRJAQDCHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-bromo-4-tert-butyl-6-(hydroxymethyl)phenol 在 盐酸 、 sodium hydroxide 作用下， 反应 36.0h， 生成 2-(3-bromo-5-tert-butylsalicyl)-5-tert-butyl-2-hydroxybenzyl alcohol
  参考文献：
  名称：

  Calixarenes. 4. The synthesis, characterization, and properties of the calixarenes from p-tert-butylphenol

  摘要：

  DOI：

  10.1021/ja00403a028
• 作为产物：
  描述：

  5-叔丁基-3-溴水杨醛 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以92%的产率得到2-bromo-4-tert-butyl-6-(hydroxymethyl)phenol
  参考文献：
  名称：

  Studies on Enzyme-Cleavable Dialkoxymethyl-cycloSaligenyl-2′,3′-dideoxy-2′,3′-didehydrothymidine Monophosphates

  摘要：

  Recently we reported on conceptually new enzymatically activated cycloSal-pronucleotides. Now, we developed this concept further with new compounds of this type. The basic idea is fast intracellular cleavage of a functionalized group at the cycloSal residue that results in a rapid delivery of the nucleotide and thus an intracellular enrichment of the nucleotide. The introduction of a higher alkylated acylal group, the di-iso-butyryloxymethyl group, to the aromatic ring led to the expected higher stability of these prodrugs against enzymatic cleavage but also entailed surprisingly a decrease in hydrolysis stabilities and solubility problems. For some compounds, a separation of the two diastereomeric forms (R-P, or S-P) was achieved. By X-ray structure analysis, the absolute configuration at the P-atom was assigned. For all separated diastereomers the (S-P) form showed better antiviral activity than the (R-P) form.

  DOI：

  10.1021/jm800853p

文献信息

• Ertul; Bayrakci, Polish Journal of Chemistry, 2009, vol. 83, # 3, p. 493 - 502
  作者：Ertul、Bayrakci

  DOI：——

  日期：——
• GUTSCHE, C. D.;DHAWAN, B.;NO, KWANG, HYUN;MUTHUKRISHNAN, RAMAMURTHI, J. AMER. CHEM. SOC., 1981, 103, N 13, 3782-3792
  作者：GUTSCHE, C. D.、DHAWAN, B.、NO, KWANG, HYUN、MUTHUKRISHNAN, RAMAMURTHI

  DOI：——

  日期：——
• US3981929A
  申请人：——

  公开号：US3981929A

  公开（公告）日：1976-09-21
• Studies on Enzyme-Cleavable Dialkoxymethyl-<i>cyclo</i>Saligenyl-2′,3′-dideoxy-2′,3′-didehydrothymidine Monophosphates
  作者：Nicolas Gisch、Jan Balzarini、Chris Meier

  DOI：10.1021/jm800853p

  日期：2008.11.13

  Recently we reported on conceptually new enzymatically activated cycloSal-pronucleotides. Now, we developed this concept further with new compounds of this type. The basic idea is fast intracellular cleavage of a functionalized group at the cycloSal residue that results in a rapid delivery of the nucleotide and thus an intracellular enrichment of the nucleotide. The introduction of a higher alkylated acylal group, the di-iso-butyryloxymethyl group, to the aromatic ring led to the expected higher stability of these prodrugs against enzymatic cleavage but also entailed surprisingly a decrease in hydrolysis stabilities and solubility problems. For some compounds, a separation of the two diastereomeric forms (R-P, or S-P) was achieved. By X-ray structure analysis, the absolute configuration at the P-atom was assigned. For all separated diastereomers the (S-P) form showed better antiviral activity than the (R-P) form.
• Calixarenes. 4. The synthesis, characterization, and properties of the calixarenes from p-tert-butylphenol
  作者：C. David Gutsche、Balram Dhawan、Kwang Hyun No、Ramamurthi Muthukrishnan

  DOI：10.1021/ja00403a028

  日期：1981.7