4-bromomethyl-1,3-dioxol-2-one | 80715-25-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: 4-bromomethyl-1,3-dioxol-2-one
• 英文别名: 4-(Bromomethyl)-1,3-dioxol-2-one
• CAS: 80715-25-9
• 化学式: C₄H₃BrO₃
• 分子量: 178.97
• InChiKey: KFZJRSPXJHVSCX-UHFFFAOYSA-N

物化性质

• 沸点：
  172.5±42.0 °C(Predicted)
• 密度：
  1.927±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  8
• 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：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-bromomethyl-1,3-dioxol-2-one 在 甲酸 、 三甲胺 作用下， 以 水 、 乙腈 为溶剂， 以82%的产率得到4-甲酰基-5-甲基-1,3-间二氧杂环戊烯-2-酮
  参考文献：
  名称：

  Dioxolenylmethyl carbamates pro moieties for amine drugs

  摘要：

  这项发明涉及使用新的氧二氧杂环己基甲基氨基甲酸酯，从一次和二次胺中制备生物可逆中性前药。

  公开号：

  US05466811A1
• 作为产物：
  描述：

  碳酸丙烯酯 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 氯 作用下， 生成 4-bromomethyl-1,3-dioxol-2-one
  参考文献：
  名称：

  Hetero-atom substituted chromium allyls: Synthetic studies on neocarzinostatin chromophore analogues

  摘要：

  DOI：

  10.1016/s0040-4039(00)97126-0

文献信息

• 1,3-dioxol-2-one derivatives
  申请人：Kanebo Ltd.

  公开号：US04777267A1

  公开（公告）日：1988-10-11

  A 1,3-dioxol-2-one derivative represented by the following formula (I) ##STR1## wherein R.sup.1 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 represent independently a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a nitro group, a carboxyl group, salts of the carboxyl group, a sulfo group and salts of the sulfo group, and a process for producing the 1,3-dioxol-2-one derivative. The compound is useful for measuring the activity of arylesterase.

  以下是用以下公式（I）表示的1,3-二氧杂环戊二酮衍生物 ##STR1## 其中R.sup.1代表氢原子或具有1至4个碳原子的烷基基团，R.sup.2、R.sup.3、R.sup.4、R.sup.5和R.sup.6分别独立代表氢原子、卤素原子、具有1至4个碳原子的烷基基团、具有1至4个碳原子的烷氧基团、硝基团、羧基、羧基的盐、磺酸基和磺酸基的盐，以及生产1,3-二氧杂环戊二酮衍生物的方法。该化合物可用于测量芳基酯酶的活性。
• 2-Oxo-1,3-dioxoles as Specific Substrates for Measurement of Arylesterase Activity.
  作者：Hiroshi KAWAI、Fumio SAKAMOTO、Masahiro TAGUCHI、Mikiya KITAMURA、Mikio SOTOMURA、Goro TSUKAMOTO

  DOI：10.1248/cpb.39.1422

  日期：——

  Various 4-arylthiomethyl-2-oxo-1, 3-dioxole derivatives IIIa-o were synthesized. Their hydrolysis rates by arylesterase (EC 3.1.1.2) and cholinesterase (EC 3.1.1.8) in human serum were evaluated. Some of them were not hydrolyzed by cholinesterase, but were hydrolyzed easily by arylesterase.Among the substrates, sodium 4-((5-methyl-2-oxo-1, 3-dioxol-4-yl)methylthio)benzenesulfonate (IIIg) was selected for its substrate reactivity toward arylesterase and its good water solubility. In addition, neither aliesterase (EC 3.1.1.1), acetylesterase (EC 3.1.1.6) nor cholesterol esterase (EC 3.1.1.13)hydrolyzed the compound. IIIg is thus concluded to be a specific substrate for arylesterase.Our assay system for serum arylesterase using IIIg can be readily applied to an automatic analyzer in the diagnosis of liver cirrhosis.

  合成了多种4-芳基硫甲基-2-氧代-1,3-二恶烷衍生物IIIa-o。评估了它们在人体血清中被芳香酯酶（EC 3.1.1.2）和胆碱酯酶（EC 3.1.1.8）水解的速率。其中一些化合物未被胆碱酯酶水解，但被芳香酯酶轻易水解。在这些底物中，选择了四-(5-甲基-2-氧代-1,3-二恶烷-4-基)甲基硫苯磺酸钠（IIIg），因为它对芳香酯酶的底物反应性以及良好的水溶性。此外，外源酯酶（EC 3.1.1.1）、乙酰酯酶（EC 3.1.1.6）和胆固醇酯酶（EC 3.1.1.13）均未能水解该化合物。因此，得出结论，IIIg是芳香酯酶的特异性底物。我们使用IIIg的血清芳香酯酶测定系统可以方便地应用于自动分析仪中，以诊断肝硬化。
• Studies on prodrugs. II. Preparation and characterization of (5-substituted 2-Oxo-1,3-dioxolen-4-yl)methyl esters of ampicillin.
  作者：FUMIO SAKAMOTO、SHOJI IKEDA、GORO TSUKAMOTO

  DOI：10.1248/cpb.32.2241

  日期：——

  (5-Substituted 2-oxo-1, 3-dioxolen-4-yl) methyl esters were designed as a new type of ampicillin prodrug. These esters were prepared and confirmed to produce higher blood levels of ampicillin than ampicillin trihydrate itself after oral administration to mice. The compounds which produced particularly high blood levels of ampicillin were found to be hydrolyzed readily in blood in vitro. Ampicillin (5-methyl-2-oxo-1, 3-dioxolen-4-yl) methyl ester hydrochloride (KBT-1585) showed the best oral absorbability in mice.

  (5-取代的2-氧基-1,3-二恶烷-4-基)甲酸酯被设计为一种新型的青霉素前药。这些酯类化合物的制备经过确认，在小鼠口服给药后能产生比青霉素三水合物本身更高的血药浓度。那些能显著提高青霉素血药浓度的化合物在体外血液中容易水解。青霉素（5-甲基-2-氧基-1,3-二恶烷-4-基）甲酸酯盐酸盐（KBT-1585）在小鼠中显示出最佳的口服吸收性。
• Studies on prodrugs. IV. Preparation and characterization of N-(5-substituted 2-oxo-1,3-dioxol-4-yl)methyl norfloxacin.
  作者：FUMIO SAKAMOTO、SHOJI IKEDA、HIROSATO KONDO、GORO TSUKAMOTO

  DOI：10.1248/cpb.33.4870

  日期：——

  As a new type of norfloxacin (NFLX) prodrug, N-(5-substituted 2-oxo-1, 3-dioxol-4-yl) methyl NFLXs were designed. These N-masked NFLXs were prepared and confirmed to produce higher NFLX levels in blood than NFLX itself after oral administration to mice. N-(5-Methyl-2-oxo-1, 3-dioxol-4-yl) methyl NFLX was found to be smoothly hydrolyzed in mouse blood in vitro, and when administered orally, gave about 5-fold higher blood levels of NFLX than NFLX itself. Thus, the (5-methyl-2-oxo-1, 3-dioxol-4-yl) methyl group was confirmed to function as an amine-type promoiety.

  作为一种新型的诺氟沙星（NFLX）前药，设计了N-(5-取代的2-氧代-1,3-二噁烷-4-基)甲基NFLX。这些N掩蔽的NFLX被制备并确认在口服给药给小鼠后，其血液中的NFLX水平高于NFLX本身。研究发现，N-(5-甲基-2-氧代-1,3-二噁烷-4-基)甲基NFLX在小鼠血液中体外平稳水解，口服给药后，NFLX的血液水平约为NFLX本身的5倍。因此，(5-甲基-2-氧代-1,3-二噁烷-4-基)甲基基团被确认具有胺型促活基的功能。
• 1,3-Dioxolen-2-one derivatives and process for production thereof
  申请人：Kanebo Ltd.

  公开号：US04342693A1

  公开（公告）日：1982-08-03

  A 1,3-dioxolen-2-one derivative of the general formula ##STR1## wherein R.sub.1 represents a hydrogen atom, a methyl group, or an aryl group, R.sub.2 represents a hydrogen atom, or may be taken together with R.sub.1 to form a divalent carbon chain residue, and x represents a halogen atom. The above compounds can be prepared by reacting a compound of the general formula ##STR2## with a halogenating agent, and are useful as protective group-introducing reagents for introducing protective groups into reagents in various chemical reactions, or as modifiers for prodrug preparation in medicine.

  一种通式为##STR1##的1,3-二氧杂环戊二酮衍生物，其中R.sub.1代表氢原子、甲基基团或芳基，R.sub.2代表氢原子，或者可以与R.sub.1一起形成二价碳链残基，x代表卤原子。上述化合物可通过将通式为##STR2##的化合物与卤化试剂反应制备，并且可用作用于各种化学反应中引入保护基的试剂，或者用作医学中的前药制备修饰剂。