2,2-二甲氧基-3-氟-1-丙醇 | 62741-32-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2,2-二甲氧基-3-氟-1-丙醇
• 英文名称: 3-fluoro-2,2-dimethoxy-propan-1-ol
• 英文别名: 1-Propanol, 2,2-dimethoxy-3-fluoro-；3-fluoro-2,2-dimethoxypropan-1-ol
• CAS: 62741-32-6
• 化学式: C₅H₁₁FO₃
• 分子量: 138.139
• InChiKey: ZUKGMEYVHPXNTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2-二甲氧基-3-氟-1-丙醇 在 盐酸 作用下， 生成 1-氟-3-羟基-2-丙酮
  参考文献：
  名称：

  3-Fluoro-1-hydroxypropan-2-one (fluorohydroxyacetone) and some esters. Syntheses and effects in BDF1 mice

  摘要：

  1-(Benzoyloxy), 1-(4-nitrobenzoyloxy), and 1-(3,5-dinitrobenzoyloxy) derivatives of 3-fluoro-, 3-chloro-, and 3-bromopropan-2-one were prepared by oxidation of the 1-benzoyloxy-3-halopropan-2-ols in turn prepared from the appropriate benzoyl chloride and 3-halo-1,2-propanediols, 1-Benzoyloxy-3-fluoropropan-2-one was allowed to react with acidic trimethyl orthoformate to yeild 1-benzoyloxy-2,2-dimethoxy-3-fluoropropane which upon basic hydrolysis afforded 2, 2-dimethoxy-3-fluoropropan-1-ol (fluorohydroxyacetone dimethyl ketal). This was deketalized with aqueous HCL to afford 3-fluoro-1-hydroxypropan-2-one (fluorohydroxyacetone), the title compound. By reacting 1-chloro-3-fluoropropan-2-one and 1, 3-dichloropropan-2-one with potassium acetate, 1-acetoxy-3-fluoropropan-2-one and 1-acetoxy-3-chloropropan-2-one (fluoro- and chlorohydroxyacetone acetate, respectively) were obtained. Similarly, sodium benzoate and 1-chloropropan-2-one produced 1-benzoyloxypropan-2-one. Stucture-activity relationships are discussed which relate chemical structure, alkylating ability, toxicity, and antitumor effects. Comparative toxicities in mice showed decreasing toxicity, on a molar basis, in the 1-benzoyloxy-3-halopropan-2-one series of bromo greater than fluoro greater than chloro. Ketones were much more toxic than the corresponding alcohols. In general the phosphate and benzoyloxy derivatives are more toxic than acetoxy compounds, with nitro-substituted benzoyloxy derivatives being much less toxic.

  DOI：

  10.1021/jm00215a005
• 作为产物：
  描述：

  2,2-二甲氧基-3-氟苯甲酸丙酯 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 2,2-二甲氧基-3-氟-1-丙醇
  参考文献：
  名称：

  3-Fluoro-1-hydroxypropan-2-one (fluorohydroxyacetone) and some esters. Syntheses and effects in BDF1 mice

  摘要：

  1-(Benzoyloxy), 1-(4-nitrobenzoyloxy), and 1-(3,5-dinitrobenzoyloxy) derivatives of 3-fluoro-, 3-chloro-, and 3-bromopropan-2-one were prepared by oxidation of the 1-benzoyloxy-3-halopropan-2-ols in turn prepared from the appropriate benzoyl chloride and 3-halo-1,2-propanediols, 1-Benzoyloxy-3-fluoropropan-2-one was allowed to react with acidic trimethyl orthoformate to yeild 1-benzoyloxy-2,2-dimethoxy-3-fluoropropane which upon basic hydrolysis afforded 2, 2-dimethoxy-3-fluoropropan-1-ol (fluorohydroxyacetone dimethyl ketal). This was deketalized with aqueous HCL to afford 3-fluoro-1-hydroxypropan-2-one (fluorohydroxyacetone), the title compound. By reacting 1-chloro-3-fluoropropan-2-one and 1, 3-dichloropropan-2-one with potassium acetate, 1-acetoxy-3-fluoropropan-2-one and 1-acetoxy-3-chloropropan-2-one (fluoro- and chlorohydroxyacetone acetate, respectively) were obtained. Similarly, sodium benzoate and 1-chloropropan-2-one produced 1-benzoyloxypropan-2-one. Stucture-activity relationships are discussed which relate chemical structure, alkylating ability, toxicity, and antitumor effects. Comparative toxicities in mice showed decreasing toxicity, on a molar basis, in the 1-benzoyloxy-3-halopropan-2-one series of bromo greater than fluoro greater than chloro. Ketones were much more toxic than the corresponding alcohols. In general the phosphate and benzoyloxy derivatives are more toxic than acetoxy compounds, with nitro-substituted benzoyloxy derivatives being much less toxic.

  DOI：

  10.1021/jm00215a005

文献信息

• Synthesis and properties of halohydroxyacetones and halomethylglyoxals
  作者：Ravi V. J. Chari、John W. Kozarich

  DOI：10.1021/jo00133a023

  日期：1982.6
• Fluoromethylglyoxal: synthesis and glyoxalase I catalyzed product partitioning via a presumed enediol intermediate
  作者：John W. Kozarich、Ravi V. J. Chari、John C. Wu、Timothy L. Lawrence

  DOI：10.1021/ja00405a057

  日期：1981.7
• PERO R. W.; BABIARZ-TRACY P.; FONDY T. P., J. MED. CHEM., 1977, 20, NO 5, 644-647
  作者：PERO R. W.、 BABIARZ-TRACY P.、 FONDY T. P.

  DOI：——

  日期：——
• 3-Fluoro-1-hydroxypropan-2-one (fluorohydroxyacetone) and some esters. Syntheses and effects in BDF1 mice
  作者：Richard W. Pero、Paula Babiarz-Tracy、Thomas P. Fondy

  DOI：10.1021/jm00215a005

  日期：1977.5

  1-(Benzoyloxy), 1-(4-nitrobenzoyloxy), and 1-(3,5-dinitrobenzoyloxy) derivatives of 3-fluoro-, 3-chloro-, and 3-bromopropan-2-one were prepared by oxidation of the 1-benzoyloxy-3-halopropan-2-ols in turn prepared from the appropriate benzoyl chloride and 3-halo-1,2-propanediols, 1-Benzoyloxy-3-fluoropropan-2-one was allowed to react with acidic trimethyl orthoformate to yeild 1-benzoyloxy-2,2-dimethoxy-3-fluoropropane which upon basic hydrolysis afforded 2, 2-dimethoxy-3-fluoropropan-1-ol (fluorohydroxyacetone dimethyl ketal). This was deketalized with aqueous HCL to afford 3-fluoro-1-hydroxypropan-2-one (fluorohydroxyacetone), the title compound. By reacting 1-chloro-3-fluoropropan-2-one and 1, 3-dichloropropan-2-one with potassium acetate, 1-acetoxy-3-fluoropropan-2-one and 1-acetoxy-3-chloropropan-2-one (fluoro- and chlorohydroxyacetone acetate, respectively) were obtained. Similarly, sodium benzoate and 1-chloropropan-2-one produced 1-benzoyloxypropan-2-one. Stucture-activity relationships are discussed which relate chemical structure, alkylating ability, toxicity, and antitumor effects. Comparative toxicities in mice showed decreasing toxicity, on a molar basis, in the 1-benzoyloxy-3-halopropan-2-one series of bromo greater than fluoro greater than chloro. Ketones were much more toxic than the corresponding alcohols. In general the phosphate and benzoyloxy derivatives are more toxic than acetoxy compounds, with nitro-substituted benzoyloxy derivatives being much less toxic.
• CHARI, R. V. J.;KOZARICH, J. W., J. ORG. CHEM., 1982, 47, N 12, 2355-2358
  作者：CHARI, R. V. J.、KOZARICH, J. W.

  DOI：——

  日期：——