N,N-二甲基-4,5-二碘-1H-咪唑-1-磺酰胺 | 198127-92-3

• 物质功能分类: 原料药 - 人工合成抗感染类药 - 磺胺类药及增效剂
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: N,N-二甲基-4,5-二碘-1H-咪唑-1-磺酰胺
• 中文别名: N,N-二甲基4,5-二碘-1H-咪唑-1-磺酰胺
• 英文名称: 4,5-diiodo-1-(N,N-dimethylsulfamoyl)-1H-imidazole
• 英文别名: 4,5-diiodo-N,N-dimethyl-1H-imidazole-1-sulfonamide；4,5-diiodo-N,N-dimethylimidazole-1-sulfonamide
• CAS: 198127-92-3
• 化学式: C₅H₇I₂N₃O₂S
• mdl: MFCD02179532
• 分子量: 427.004
• InChiKey: BRCLUKJLHQKEGH-UHFFFAOYSA-N

物化性质

• 沸点：
  444.3±55.0 °C(Predicted)
• 密度：
  2.59±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  63.6
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2935009090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: N,N-Dimethyl 4,5-diiodo-1H-imidazole-1-sulfonamide
Synonyms:

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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: N,N-Dimethyl 4,5-diiodo-1H-imidazole-1-sulfonamide
CAS number: 198127-92-3

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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: C5H7I2N3O2S
Molecular weight: 427.0

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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, sulfur oxides.

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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：

  N,N-二甲基-4,5-二碘-1H-咪唑-1-磺酰胺 在 copper(I) cyanide di(lithium chloride) 、 乙基溴化镁 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 48.33h， 生成 4-(4-benzyloxy-3,5-dimethoxybenzyl)-1-(N,N-dimethylsulfonyl)-5-(4-methoxybenzyl)-1H-imidazole
  参考文献：
  名称：

  Leucetta生物碱的总合成和细胞毒性

  摘要：

  描述了从含有多取代的2-氨基咪唑的Leucetta和Clathrina海绵分离的许多代表性天然产物的全合成。这些合成利用了4,5-二碘咪唑的位点特定的金属化反应，从而合成了三类不同的Leucetta衍生的天然产物。通过MTT生长测定法确定了这些天然产物以及MCF7细胞中的几种前体的细胞毒性。为了比较起见，包括一系列含萘咪唑的家族成员。

  DOI：

  10.1016/j.bmc.2017.01.024
• 作为产物：
  描述：

  4,5-二碘咪唑 、 二甲胺基磺酰氯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以62%的产率得到N,N-二甲基-4,5-二碘-1H-咪唑-1-磺酰胺
  参考文献：
  名称：

  Synthesis and Diels−Alder Reactions of 4-Vinylimidazoles

  摘要：

  [GRAPHICS]The synthesis of several 4-vinylimidazoles via Stille cross-coupling reactions of the corresponding protected 4-iodoimidazoles with tributylvinylstannane is described, These heterocyclic dienes are shown to be effective partners in the Diels-Alder reaction, providing adducts in good yield acid exhibiting useful levels of isomer selectivity and stereoselectivity (endo/exo).

  DOI：

  10.1021/ol015687m

文献信息

• Total Synthesis of the Nagelamides – Synthetic Studies toward the Reported Structure of Nagelamide D and Nagelamide E Framework
  作者：Manojkumar R. Bhandari、Apsara K. Herath、Sivappa Rasapalli、Muhammed Yousufuddin、Carl J. Lovely

  DOI：10.1021/acs.joc.0c01617

  日期：2020.10.16

  closely related oroidin alkaloids, supporting the structure of the synthetic material. The structure of the synthetic material was further corroborated by obtaining an X-ray crystal structure of a derivative. Electrocyclization of an advanced precursor affords a dihydrobenzimidazole, which is expected to serve as a key intermediate en route to nagelamide E and ageliferin.

  nagelamides 是源自海洋海绵的生物碱 Oroidin 家族的一小部分，并且大部分本质上是二聚体。作为我们开发该家族合成途径的努力的一部分，使用 Stille 交叉偶联策略来构建双咪唑基核心骨架。双乙烯基咪唑的还原提供了 nagelamide D 的核心框架。通过相应的叠氮化物引入 2-氨基，并使用吡咯乙内酰脲通过双 Mitsunobu 反应引入吡咯酰胺，提供了 nagelamide D 的推定结构。光谱数据合成材料和海绵衍生材料匹配得不太好，而光谱数据与密切相关的兰花苷生物碱匹配良好，支持了合成​​材料的结构。通过获得衍生物的X射线晶体结构，进一步证实了合成材料的结构。高级前体的电环化得到二氢苯并咪唑，预计其将作为 nagelamide E 和阿吉利林的关键中间体。
• Total Synthesis of the Putative Structure of Nagelamide D
  作者：Manojkumar R. Bhandari、Rasapalli Sivappa、Carl J. Lovely

  DOI：10.1021/ol9001762

  日期：2009.4.2

  A total synthesis of the putative structure of nagelamide D from imidazole is described. A Stille cross-coupling is used to construct the bis imidazole skeleton, and the pyrrolecarboxamides are introduced via a double Mitsunobu reaction using a pyrrolehydantoin derivative. Discrepancies between the published spectroscopic data and that reported in the literature cast doubts either on the assigned structure

  描述了从咪唑全合成 nagelamide D 的推定结构。Stille 交叉偶联用于构建双咪唑骨架，并通过使用吡咯乙内酰脲衍生物的双光信反应引入吡咯甲酰胺。已发表的光谱数据与文献中报告的数据之间的差异使人们对指定的结构或报告的数据产生怀疑。
• Preparation and Diels−Alder Chemistry of 4-Vinylimidazoles
  作者：Carl J. Lovely、Hongwang Du、Rasapalli Sivappa、Manojkumar R. Bhandari、Yong He、H. V. Rasika Dias

  DOI：10.1021/jo0626008

  日期：2007.5.1

  circumvented to a large extent by the choice of reaction conditions. Limited reactions were observed with other dienophiles, providing the expected cycloadducts in most cases, although an abnormal adduct was obtained in one case with dimethyl acetylene dicarboxylate. These substrates also participate in regioselective Diels−Alder reactions with monoactivated dienophiles, but require fairly forcing conditions

  从相应的4-碘咪唑或从尿酸制备了各种4-乙烯基咪唑衍生物。报道了几种详细说明这些乙烯基咪唑及其Diels-Alder反应的方法。在本研究过程中制备的所有乙烯基咪唑均与N反应-苯基马来酰亚胺很容易被温和的热活化而形成单个环加合物，在大多数情况下是初始的非芳族加合物。对于更多的富电子底物，尽管可以通过选择反应条件在很大程度上避免这些初始环加合物发生芳构化，烯键反应和氧化的趋势。观察到与其他亲二烯体的反应有限，在大多数情况下可提供预期的环加合物，尽管在一种情况下，与乙炔二甲酸二甲酯反应可得到异常的加合物。这些底物还与单活化的亲二烯体参与区域选择性Diels-Alder反应，但需要相当强的条件，因此仅以适度的收率提供了芳构化的环加合物。对咪唑部分2-位的取代基作用进行了研究，在其中耐受给电子和弱吸电子的取代基。另外，已经研究了具有末端取代的乙烯基部分的几种底物。
• Stille Cross-Coupling for the Functionalization of the Imidazole Backbone: Revisit, Improvement, and Applications of the Method
  作者：Alexander H. Sandtorv、Karl Wilhelm Törnroos、Hans-René Bjørsvik

  DOI：10.1002/ejoc.201500328

  日期：2015.6

  We have revisited the Stille coupling reaction for the functionalization of the imidazole backbone. In this context CuI was exploited as a co-catalyst, which resulted in significantly improved yields of target coupling products. Furthermore, a systematic investigation of the effect of the auxiliary group on the N-1-ring atom was performed. When mono-coupling is desired, the Tosyl (Tos) group is superior

  我们重新审视了用于咪唑骨架功能化的 Stille 偶联反应。在这种情况下，CuI 被用作助催化剂，从而显着提高了目标偶联产物的产率。此外，还对辅助基团对 N-1 环原子的影响进行了系统研究。当需要单偶联时，甲苯磺酰基 (Tos) 基团优于（二甲氨基）磺酰基 (DMAS) 基团，以显着更高的产率提供相应的 4 偶联咪唑。然而，当首选双耦合时，DMAS 组对于耦合程序的成功是必不可少的。利用该反应协议，我们成功地展示了使用 N-DMAS-4,5-二碘咪唑作为底物的 Stille 双偶联的第一个例子。
• Concise total synthesis of naamine G and naamidine H
  作者：Panduka B. Koswatta、Carl J. Lovely

  DOI：10.1039/b926285g

  日期：——

  Total syntheses of the cytotoxic Leucetta-derived 2-aminoimidazoles, naamine G and naamidine H, have been accomplished using a position selective metalation–benzylation sequence with a 4,5-diiodoimidazole derivative.

  已完成细胞毒性Leucetta衍生的2-氨基咪唑，naamine G和naamidine H的总合成，采用了选择性金属化-苄基化序列，使用了4,5-二碘咪唑衍生物。