5-碘-2-嘧啶酮 | 79387-69-2

• 物质功能分类: 医药中间体 - 杂环化合物 - 嘧啶类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 5-碘-2-嘧啶酮
• 中文别名: 2-羟基-5-碘嘧啶
• 英文名称: 5-iodo-2(1H)-pyrimidinone
• 英文别名: 5-iodo-1H-pyrimidin-2-one
• CAS: 79387-69-2
• 化学式: C₄H₃IN₂O
• 分子量: 221.985
• InChiKey: PVHCYDBPRLPQMP-UHFFFAOYSA-N

物化性质

• 密度：
  2.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2933599090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  2-8°C

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Hydroxy-5-iodopyrimidine
Synonyms: 5-Iodo-2-pyrimidinone

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

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Section 3. Composition/information on ingredients.
Ingredient name: 2-Hydroxy-5-iodopyrimidine
CAS number: 79387-69-2

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Section 4. First aid measures
Skin contact: Immediately wash skin with copious amounts of water for at least 15 minutes while removing
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Ingestion: Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Store in closed vessels, refrigerated.
Storage:

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Appearance: Not specified
Boiling point: No data
No data
Melting point:
Flash point: No data
Density: No data
Molecular formula: C4H3IN2O
Molecular weight: 222.0

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides, hydrogen Iodide.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  5-碘-2-嘧啶酮 生成 5-iodo-2-((trimethylsilyl)oxy)pyrimidine
  参考文献：
  名称：

  Organic Process Research and Development. 1999, 3, 135-138

  摘要：

  DOI：
• 作为产物：
  描述：

  2-羟基嘧啶盐酸盐 在 N-碘代丁二酰亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 5-碘-2-嘧啶酮
  参考文献：
  名称：

  α-吡喃酮和嘧啶酮作为基于亲和力的蛋白质谱分析的光亲和探针的评价

  摘要：

  α-吡喃酮和嘧啶酮是天然产物和生物活性化合物中常见的结构基序。它们还显示出产生高能中间体的光化学，该中间体可能具有蛋白质反应性。合成了吡喃酮和嘧啶酮的文库，并评估了它们在几种粗细胞裂解物中用作基于非定向亲和力的蛋白质谱分析的光亲和探针的潜力。进一步的“原理证明”实验表明，适当支架上的嘧啶酮标签具有与二苯甲酮同样的蛋白质组标记能力。

  DOI：

  10.1021/jo201281c

文献信息

• Substituted pyrimidin-2-ones, the salts thereof, processes for their
  申请人：Glaxo Group Limited

  公开号：US04636509A1

  公开（公告）日：1987-01-13

  Compounds of the general formula: ##STR1## (wherein X represents a halogen atom or a trifluoromethyl group; R.sup.1 represents an optionally substituted C.sub.6-10 carbocyclic aromatic group; and R.sup.2 represents a hydrogen atom or a lower alkyl, C.sub.7-16 aralkyl or C.sub.6-10 aryl group or the group COR.sup.1a, in which R.sup.1a is as defined for R.sup.1, R.sup.1 and R.sup.1a being the same or different) and where an acidic or basic group is present, the salts thereof have been found to possess excellent metaphase arresting ability and are of use in combating abnormal cell proliferation. Thus a knowledge of the cell division cycles of the normal and abnormal cells enables a cytotoxic drug to be administered while the abnormal cells are in a phase susceptible to attack and while the normal cells are in a non-susceptible phase. The compounds of the invention are prepared by alkylation, deprotection of a protected keto group, oxidation or electrophilic halogenation. Pharmaceutical compositions containing the compounds of formula I, and where appropriate, the physiologically compatible salts thereof; and methods for the use of the compounds are described and claimed.

  通式为：##STR1##（其中X代表卤原子或三氟甲基基团；R.sup.1代表可选择取代的C.sub.6-10碳环芳基团；R.sup.2代表氢原子或较低的烷基、C.sub.7-16芳基烷基或C.sub.6-10芳基团或基团COR.sup.1a，其中R.sup.1a如R.sup.1所定义，R.sup.1和R.sup.1a相同或不同）并且存在酸性或碱性基团，已发现其盐具有出色的中期阻滞能力，并可用于对抗异常细胞增殖。因此，了解正常和异常细胞的细胞分裂周期使得可以在异常细胞处于易受攻击阶段而正常细胞处于不易受攻击阶段时给予细胞毒性药物。本发明的化合物通过烷基化、去保护受保护的酮基团、氧化或亲电卤代反应制备。描述和声明了含有通式I化合物的药物组合物，以及在适当情况下其生理相容盐；并描述和声明了使用这些化合物的方法。
• Substituted pyrimidin-2-ones and the salts thereof
  申请人：Nyegaard & Co. A.S.

  公开号：US04596870A1

  公开（公告）日：1986-06-24

  Compounds of the general formula: ##STR1## (wherein X represents a halogen atom or a trifluoromethyl group; R.sup.1 and R.sup.2 independently represent a hydrogen atom or a lower alkyl group; Z is --O--, --S--, --SO--, --SO.sub.2 -- or the group --NR.sup.4 -- wherein R.sup.4 is as defined for R hereinafter or represents the group COR.sup.5 in which R.sup.5 represents a hydrogen atom or an optionally substituted aryl, heterocyclic, aralkyl, lower alkyl or lower alkoxy group; R represents a C.sub.6-10 carbocyclic aromatic group or a heterocyclic group containing a 5-9 membered unsaturated or aromatic heterocyclic ring which ring contains one or more heteroatoms selected from O, N and S and optionally carries a fused ring which carbocyclic or heterocyclic group may carry one or more C.sub.1-4 alkyl or phenyl groups, said groups being optionally substituted; or, where Z represents the group >NR.sup.4, the group --ZR may represent a heterocyclic ring optionally carrying a fused ring and/or optionally substituted as defined for R; and R.sup.3 represents a hydrogen atom or a lower alkyl, lower alkenyl, lower alkynyl, lower alkanoyl, lower alkenoyl, C.sub.7-16 aralkyl or C.sub.6-10 arly group or a 5-9 membered unsaturated or aromatic heterocyclic ring); and, where acid or basic groups are present, the salts thereof; are useful in combating abnormal cell proliferation. The compounds of the invention are prepared by inter alia alkylation, ring closure and oxidation.

  通式为：##STR1## 的化合物（其中X代表卤素原子或三氟甲基基团；R.sup.1和R.sup.2分别代表氢原子或较低的烷基基团；Z为--O--，--S--，--SO--，--SO.sub.2 --或基团--NR.sup.4 --其中R.sup.4如下所定义或代表基团COR.sup.5，其中R.sup.5代表氢原子或可选择取代的芳香族、杂环、芳基烷基、较低的烷基或较低的烷氧基团；R代表C.sub.6-10碳环芳族或含有5-9个成员的不饱和或芳香杂环环，该环含有O、N和S中选定的一个或多个杂原子，并且可选择携带一个融合环的碳环或杂环基团，该碳环或杂环基团可以携带一个或多个C.sub.1-4烷基或苯基基团，这些基团可选择取代；或者，Z代表基团>NR.sup.4时，基团--ZR可以代表一个可选择携带一个融合环和/或可选择取代的杂环环，如R所定义；R.sup.3代表氢原子或较低的烷基、较低的烯基、较低的炔基、较低的烷酰基、较低的烯酰基、C.sub.7-16芳基烷基或C.sub.6-10芳基基团或一个5-9成员的不饱和或芳香杂环环）；并且，如有酸性或碱性基团存在，其盐；在对抗异常细胞增殖方面是有用的。该发明的化合物是通过烷基化、环闭合和氧化等方法制备的。
• 5-Halo-pyrimidin-2-ones, the salts thereof
  申请人：Nyegaard & Co. A/S

  公开号：US04399140A1

  公开（公告）日：1983-08-16

  Compounds of the formula: ##STR1## wherein X represents a halogen atom; R.sup.1 and R.sup.2, which may be same or different, each represents a hydrogen atom, or a C.sub.1-4 alkyl group; Het represents a C-attached 3-9 membered, saturated, unsaturated or aromatic heterocyclic ring containing one or more hetero atoms selected from O, N and S and optionally carrying a fused ring and/or optionally substituted by one or more substituents selected from halogen atoms and hydroxy, C.sub.1-4 alkoxy, amino, acylamino, nitro, oxo, C.sub.1-4 alkyl groups and monocyclic carbocyclic and heterocyclic aryl groups having 5 to 8 ring members; such a heterocyclic ring being saturated and having only a single heteroatom when there are 3 or 4 ring members; and alk represents a C.sub.1-4 saturated or unsaturated, straight or branched chain, divalent aliphatic hydrocarbyl group optionally substituted by one or more groups selected from carbocyclic aryl groups and heterocyclic groups as defined for Het above, and the salts thereof have been found to possess metaphase arresting ability which by virtue of its reversibility is of use in combating abnormal cell proliferation. Thus a knowledge of the cell division cycles of the normal and abnormal cells enables a cytotoxic drug to be administered while the abnormal cells are in a phase susceptible to attack and while the normal cells are in a non-susceptible phase. The compounds of the invention are prepared by alkylation, ring closure of the pyrimidine ring, halogenation or ring closure of the heterocyclic ring Het.

  式为：##STR1## 其中 X 代表卤原子；R.sup.1 和 R.sup.2，可能相同也可能不同，每个代表氢原子，或者 C.sub.1-4 烷基基团；Het 代表一个连接到 C 的 3-9 个成员的饱和、不饱和或芳香杂环环，其中包含一个或多个来自 O、N 和 S 的杂原子，并且可能携带一个融合环和/或可选择地被一个或多个来自卤原子和羟基、C.sub.1-4 烷氧基、氨基、酰胺基、硝基、氧代基、C.sub.1-4 烷基基团和含有 5 到 8 个环成员的单环碳环和杂环芳基团取代的取代基；当有 3 或 4 个环成员时，这样的杂环环是饱和的，并且只有一个杂原子；alk 代表一个 C.sub.1-4 饱和或不饱和的、直链或支链、双价脂肪烃基团，可选择地被一个或多个来自碳环芳基团和如上所述的 Het 的杂环基团的取代基取代，以及其盐已被发现具有相位阻滞能力，由于其可逆性，可用于对抗异常细胞增殖。因此，对正常和异常细胞的细胞分裂周期的了解使得细胞毒性药物可以在异常细胞处于易受攻击阶段而正常细胞处于非易受攻击阶段时进行给药。本发明的化合物通过烷基化、嘧啶环的环闭合、卤化或杂环环 Het 的环闭合制备。
• Substituted pyrimidin-2-ones, the salts thereof, pharmaceutical
  申请人：Glaxo Group Limited

  公开号：US04650800A1

  公开（公告）日：1987-03-17

  Compounds of the general formula: ##STR1## wherein X represents a halogen atom or a trifluoromethyl group; R.sup.1 represents a hydrogen atom or a lower alkyl group and Het represents an optionally substituted C-attached 5-7 membered aromatic heterocyclic ring which ring contains one or more heteroatoms selected from O, N and S and optionally carries a fused ring and where an acidic or basic group is present, the salts thereof have been found to possess excellent metaphase arresting ability and are of use in combating abnormal cell proliferation. Thus a knowledge of the cell division cycles of the normal and abnormal cells enables a cytotoxic drug to be administered while the abnormal cells are in a phase susceptible to attack and while the normal cells are in a non-susceptible phase. The compounds of the invention are prepared by alkylation, deprotection of a protected keto group, oxidation or electrophilic halogenation.

  通式化合物：##STR1##其中X代表卤素原子或三氟甲基；R1代表氢原子或低级烷基，Het代表可选择性取代的C连接的5-7元芳香杂环，该环含有一个或多个选自O、N和S的杂原子，并可选择性地带有融合环，且当存在酸性或碱性基团时，其盐已被发现具有优异的染色体中期阻滞能力，并可用于对抗异常细胞增殖。因此，了解正常和异常细胞的分裂周期使得可以在异常细胞处于易受攻击阶段时给予细胞毒性药物，而正常细胞处于非易受攻击阶段。本发明的化合物通过烷基化、保护酮基的去保护、氧化或亲电卤化制备。
• Synthesis and Structural Characterization of Ethynylene-Bridged Bisazines Featuring Various α-Substitution
  作者：Jörg Hübscher、Wilhelm Seichter、Thomas Gruber、Jens Kortus、Edwin Weber

  DOI：10.1002/jhet.2122

  日期：2015.7

  A series of bispyridines and bispyrimidines 1a, 1b, 1c, 1d, 1e showing the heterocycles attached to both ends of an ethynylene unit and being α‐substituted with chloro, tert‐butylthio, and methoxy groups have been synthesized via cross‐coupling technique and their crystal structures studied by X‐ray diffraction analysis. Supramolecular interactions of C–H···N and π···π stacking type were found to largely

  通过交叉偶联技术合成了一系列联吡啶和联嘧啶1a，1b，1c，1d，1e，它们显示了与亚乙炔基单元两端连接的杂环并被氯，叔丁硫基和甲氧基α-取代的杂环。通过X射线衍射分析研究了它们的晶体结构。发现C–H···N和π···π堆积类型的超分子相互作用在很大程度上取决于化合物的种类。进行了一项试验，从晶体结构的特殊特征中推断出化合物之间的熔融温度明显不同。