N-甲基-1,1-二氧代-异噻唑烷 | 83634-83-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 中文名称: N-甲基-1,1-二氧代-异噻唑烷
• 英文名称: N-methyl-1,2-isothiazolidine-1,1-dioxide
• 英文别名: 2-methylisothiazolidine-1,1-dioxide；N-methyl-1,3-propanesultam；N-methylpropanesultam；2-methyl-isothiazolidine 1,1-dioxide；2-Methyl-isothiazolidin-1,1-dioxid；N-Methyl-propansultam-(1,3)；2-Methylisothiazolidine 1,1-dioxide；2-methyl-1,2-thiazolidine 1,1-dioxide
• CAS: 83634-83-7
• 化学式: C₄H₉NO₂S
• 分子量: 135.187
• InChiKey: GGUJLVPQFOPIJU-UHFFFAOYSA-N

物化性质

• 熔点：
  48-49 °C(Solv: acetone (67-64-1))
• 沸点：
  218.8±23.0 °C(Predicted)
• 密度：
  1.271±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934100090
• 储存条件：
  存储条件：2-8°C，密封保存，并保持干燥。

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: N-Methyl-1,3-propanesultam
Synonyms: N-Methyl 1,1-dioxo-isothiazolidine

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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-Methyl-1,3-propanesultam
CAS number: 83634-83-7

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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.
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: C4H9NO2S
Molecular weight: 135.2

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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, 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：

  氟磺酸甲酯 、 N-甲基-1,1-二氧代-异噻唑烷 反应 0.5h， 以98%的产率得到2,2-dimethylisothiazolidinium 1,1-dioxide fluorosulfate
  参考文献：
  名称：

  Betylates. 3. Preparative nucleophilic substitution by way of [2]-, [3]-, and [4]betylates. Stoichiometric phase transfer and substrate-reagent ion-pair (SRIP) reactions of betylates

  摘要：

  DOI：

  10.1021/ja00389a038
• 作为产物：
  描述：

  2-甲基异噻唑烷 在 sodium periodate 作用下， 以 甲醇 、 水 为溶剂， 反应 10.0h， 以60%的产率得到N-甲基-1,1-二氧代-异噻唑烷
  参考文献：
  名称：

  Matsuyama, Haruo; Izuoka, Akira; Kobayashi, Michio, Heterocycles, 1985, vol. 23, # 8, p. 1897 - 1900

  摘要：

  DOI：

文献信息

• Stereoselective Synthesis of β-Substituted β-Amino Sulfones and Sulfonamides via Addition of Sulfonyl Anions to Chiral <i>N</i>-Sulfinyl Imines
  作者：Francisco Velázquez、Ashok Arasappan、Kevin Chen、Mousumi Sannigrahi、Srikanth Venkatraman、Andrew T. McPhail、Tze-Ming Chan、Neng-Yang Shih、F. George Njoroge

  DOI：10.1021/ol053132b

  日期：2006.2.1

  [reaction: see text] A highly stereoselective synthesis of beta-amino sulfones and sulfonamides via addition of sulfonyl anions to chiral N-sulfinyl imines is described. The addition reaction proceeds in good yield (75-99%) and stereoselectivity.

  [反应：见正文]描述了通过将磺酰基阴离子加到手性N-亚磺酰基亚胺上的β-氨基砜和磺酰胺的高度立体选择性合成。加成反应以良好的收率（75-99％）和立体选择性进行。
• A new synthesis of sultams from amino alcohols
  作者：Nitin Lad、Rajiv Sharma、Victor E. Marquez、Malcolm Mascarenhas

  DOI：10.1016/j.tetlet.2013.09.021

  日期：2013.11

  The base-mediated cyclization of N,O-dimesylate derivatives of cyclic and acyclic amino alcohols provides a simple access to five- and six-member sultams: isothiazolidine-1,1-dioxides and thiazinane-1,1-dioxides respectively. (C) 2013 Elsevier Ltd. All rights reserved.
• Novel Antiarthritic Agents with 1,2-Isothiazolidine-1,1-dioxide (γ-Sultam) Skeleton: Cytokine Suppressive Dual Inhibitors of Cyclooxygenase-2 and 5-Lipoxygenase
  作者：Masanao Inagaki、Tatsuo Tsuri、Hirokuni Jyoyama、Takashi Ono、Katsutoshi Yamada、Mika Kobayashi、Yozo Hori、Akinori Arimura、Kiyoshi Yasui、Kouji Ohno、Shinji Kakudo、Kenzo Koizumi、Ryuji Suzuki、Miyako Kato、Shinichi Kawai、Saichi Matsumoto

  DOI：10.1021/jm9906015

  日期：2000.5.1

  Various 1,2-isotkiazolidine-1,1-dioxide (gamma-sultam) derivatives containing an antioxidant moiety, 2i6-di-tert-butylphenol substituent, were prepared. Some compounds, which have a lower alkyl group at the 2-position of the gamma-sultam skeleton, showed potent inhibitory effects on both cyclooxygenase (COX)-2 and 5-lipoxygenase (5-LO), as well as production of interleukin (IL)-1 in in vitro assays. They also proved to be effective in several animal arthritic models without any ulcerogenic activities. Among these compounds, (E)-(5)-(3,5-di-tert-butyl-4-hydroxybenzyliclene)-2-ethyl-1,2-isothiazolidine-1, (S-2474) was selected as an antiarthritic drug candidate and is now under clinical trials. The structure-activity relationships (SAR) examined and some pharmacological evaluations are described.
• Discovery of potent sulfonamide P4-capped ketoamide second generation inhibitors of hepatitis C virus NS3 serine protease with favorable pharmacokinetic profiles in preclinical species
  作者：Stéphane L. Bogen、Ashok Arasappan、Francisco Velazquez、Melissa Blackman、Regina Huelgas、Weidong Pan、Elise Siegel、Latha G. Nair、Srikanth Venkatraman、Zhuyan Guo、Ronald Doll、Neng-Yang Shih、F. George Njoroge

  DOI：10.1016/j.bmc.2010.01.044

  日期：2010.3

  Hepatitis is a disease characterized by inflammation of the liver, usually producing swelling and, in many cases, permanent damage to liver tissues. Viral hepatitis C (HCV), a small (+)-RNA virus, infects chronically 3% of the world's population. Boceprevir, SCH 503034, (1) our first generation HCV inhibitor, has already established proof-of-concept and is currently in late stage (phase III) clinical trials. In view of the positive data from our first generation compound, further work aimed at optimizing its overall profile was undertaken. Herein, we report that extension of our earlier inhibitor to the P-4 pocket by introducing a new sulfonamide moiety and optimization of the P1/P-1' capping led to the discovery of a novel series of inhibitors of the HCV NS3 serine protease. Optimization of the P-1 residue significantly improved potency and selectivity. The combination of optimal moieties led to the discovery of compound 47 which, in addition to being a potent inhibitor of HCV subgenomic RNA replication, was also found to have good PK profile in rat, dog and monkey. (C) 2010 Elsevier Ltd. All rights reserved.
• Shipov, A. G.; Baukov, Yu. I., Journal of general chemistry of the USSR, 1984, vol. 54, p. 1642 - 1657
  作者：Shipov, A. G.、Baukov, Yu. I.

  DOI：——

  日期：——