5-Brom-2-hydroxy-3-methylbenzylalkohol | 77691-33-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-Brom-2-hydroxy-3-methylbenzylalkohol
• 英文别名: 5-Bromo-2-hydroxy-3-methylbenzyl alcohol；4-bromo-2-(hydroxymethyl)-6-methylphenol
• CAS: 77691-33-9
• 化学式: C₈H₉BrO₂
• mdl: MFCD16249637
• 分子量: 217.062
• InChiKey: JYYZDOXKWKNIRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  5-Brom-2-hydroxy-3-methylbenzylalkohol 在 吡啶 、 盐酸 、 叔丁基过氧化氢 、 正丁基锂 、 氯化锆(IV) 、 对甲苯磺酸 、 sodium sulfate 、 N,N-二异丙基乙胺 、 三氯化磷 作用下， 以 四氢呋喃 、 正己烷 、 丙酮 、 乙腈 为溶剂， 反应 82.25h， 生成 [acetoxy-[8-methyl-2-[[(2S,5R)-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)-2,5-dihydrofuran-2-yl]methoxy]-2-oxo-4H-1,3,2$l^{5}-benzodioxaphosphinin-6-yl]methyl] acetate
  参考文献：
  名称：

  Enzymatically Activated cycloSal-d4T-monophosphates:  The Third Generation of cycloSal-Pronucleotides

  摘要：

  The third generation of cycloSal-pronucleotides, 5-diacetoxymethyl-cycloSal-d4T-monophosphates (5-di-AM-cycloSal-d4TMPs), is reported as a new class of "lock-in"-modified cycloSal-pronucleotides. These compounds bear an esterase-cleavable geminal dicarboxylate (acylal) attached to the aromatic ring of the saligenyl unit. The conversion into a strong acceptor group (aldehyde) leads to a strong decrease in hydrolytic stability. As a consequence, a fast release of a nucleoside monophosphate (i.e., d4TMP) follows. The concept of this enzymatic activation is proven by hydrolysis studies in phosphate buffer, cell extracts, and human serum. These investigations showed the conversion of the acylal group into a polar aldehyde by enzymatic cleavage. Besides, antiviral activities against HIV are presented.

  DOI：

  10.1021/jm0613267
• 作为产物：
  描述：

  3-甲基水杨酸 在 lithium aluminium tetrahydride 、 硫酸 、 溴 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 95.0h， 生成 5-Brom-2-hydroxy-3-methylbenzylalkohol
  参考文献：
  名称：

  Enzymatically Activated cycloSal-d4T-monophosphates:  The Third Generation of cycloSal-Pronucleotides

  摘要：

  The third generation of cycloSal-pronucleotides, 5-diacetoxymethyl-cycloSal-d4T-monophosphates (5-di-AM-cycloSal-d4TMPs), is reported as a new class of "lock-in"-modified cycloSal-pronucleotides. These compounds bear an esterase-cleavable geminal dicarboxylate (acylal) attached to the aromatic ring of the saligenyl unit. The conversion into a strong acceptor group (aldehyde) leads to a strong decrease in hydrolytic stability. As a consequence, a fast release of a nucleoside monophosphate (i.e., d4TMP) follows. The concept of this enzymatic activation is proven by hydrolysis studies in phosphate buffer, cell extracts, and human serum. These investigations showed the conversion of the acylal group into a polar aldehyde by enzymatic cleavage. Besides, antiviral activities against HIV are presented.

  DOI：

  10.1021/jm0613267

文献信息

• Stein, Guenter; Boehmer, Volker; Lotz, Werner, Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1981, vol. 36, # 2, p. 231 - 241
  作者：Stein, Guenter、Boehmer, Volker、Lotz, Werner、Kaemmerer, Hermann

  DOI：——

  日期：——
• OXADIAZOLYL-PHENOXYALKYLISOXAZOLES, COMPOSITIONS THEREOF AND METHODS FOR THEIR USE AS ANTI-PICORNAVIRAL AGENTS
  申请人：Rhodes Gerald

  公开号：US20080293783A1

  公开（公告）日：2008-11-27

  Oxadiazolyl-phenoxyalkylisoxazoles and pharmaceutically acceptable salts thereof, compositions comprising oxadiazolyl-phenoxyalkylisoxazole compounds or pharmaceutically acceptable salts thereof and methods for using oxadiazolyl-phenoxyalkylisoxzazole compounds or pharmaceutically acceptable salts thereof as anti-picornaviral agents are described herein. The methods include using pleconaril as a prodrug for conversion to anti-picornaviral compounds in vivo.
• US7429606B2
  申请人：——

  公开号：US7429606B2

  公开（公告）日：2008-09-30
• US7585884B2
  申请人：——

  公开号：US7585884B2

  公开（公告）日：2009-09-08
• Enzymatically Activated <i>cyclo</i>Sal-d4T-monophosphates:  The Third Generation of <i>cyclo</i>Sal-Pronucleotides
  作者：Nicolas Gisch、Jan Balzarini、Chris Meier

  DOI：10.1021/jm0613267

  日期：2007.4.1

  The third generation of cycloSal-pronucleotides, 5-diacetoxymethyl-cycloSal-d4T-monophosphates (5-di-AM-cycloSal-d4TMPs), is reported as a new class of "lock-in"-modified cycloSal-pronucleotides. These compounds bear an esterase-cleavable geminal dicarboxylate (acylal) attached to the aromatic ring of the saligenyl unit. The conversion into a strong acceptor group (aldehyde) leads to a strong decrease in hydrolytic stability. As a consequence, a fast release of a nucleoside monophosphate (i.e., d4TMP) follows. The concept of this enzymatic activation is proven by hydrolysis studies in phosphate buffer, cell extracts, and human serum. These investigations showed the conversion of the acylal group into a polar aldehyde by enzymatic cleavage. Besides, antiviral activities against HIV are presented.