2-氨基-2-硫代乙基氨基甲酸叔丁酯 | 89226-13-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代酰胺
• 中文名称: 2-氨基-2-硫代乙基氨基甲酸叔丁酯
• 中文别名: 2-氨基-2-硫氧代乙基氨基甲酸叔丁酯
• 英文名称: 2-(N-t-butoxycarbonylamino)thioacetamide
• 英文别名: tert-butyl (2-amino-2-thioxoethyl)carbamate；tert-butyl N-(2-amino-2-thioxo-ethyl)carbamate；1,1-dimethylethyl N-(2-amino-2-thioxoethyl)carbamate；tert-butyl N-(2-amino-2-sulfanylideneethyl)carbamate
• CAS: 89226-13-1
• 化学式: C₇H₁₄N₂O₂S
• mdl: MFCD09025922
• 分子量: 190.266
• InChiKey: AGBIUUFZUPNDTM-UHFFFAOYSA-N

物化性质

• 熔点：
  129 °C
• 密度：
  1.152±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.714
• 拓扑面积：
  96.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2930909090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  2-8℃

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: tert-Butyl N-(carbamothioylmethyl)carbamate
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: tert-Butyl N-(carbamothioylmethyl)carbamate
CAS number: 89226-13-1

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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: C7H14N2O2S
Molecular weight: 190.3

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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：

  2-氨基-2-硫代乙基氨基甲酸叔丁酯 在 ammonium hydroxide 、 三乙胺 、 三氟乙酸酐 、 calcium carbonate 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 27.5h， 生成 2-{2-[(tert-butoxycarbonylamino)methyl]thiazol-4-yl}-4,5-dihydrothiazole-4-carboxylic acid
  参考文献：
  名称：

  候选前大肠杆菌素的收敛和模块化合成。Precolibactin A 的结构修正

  摘要：

  大肠杆菌素是由某些共生和肠外致病性大肠杆菌菌株产生的混合聚酮化合物-非核糖体肽天然产物。代谢物由 clb 基因簇编码，称为前体药物。clb(+) 大肠杆菌在体外和体内诱导哺乳动物细胞 DNA 双链断裂，并且在 55-67% 的结肠直肠癌患者中发现，表明成熟的大肠杆菌素可以引发肿瘤发生。然而，阐明它们的结构一直是一项艰巨的任务，因为从细菌培养物中获得的代谢物数量极少 (μg/L)，并且被认为是不稳定的。在此，我们描述了一种灵活且收敛的合成路线来制备先进的前大肠杆菌素和衍生物。合成通过两个复杂前体（例如，28 + 17 → 29a，90%），然后是碱诱导的双脱水级联反应，形成两个目标环（例如，29a → 30a，79%）。该序列提供了超过发酵获得的数量的先进候选前大肠杆菌素的数量，并且预计可以很容易地进行缩放。这些研究指导了预测代谢物 precolibactin A（从 5a 或 5b 到 7）的结构修订，并证实了分离的代谢物

  DOI：

  10.1021/jacs.6b02276
• 作为产物：
  描述：

  BOC-甘氨酸 在 劳森试剂 、 N-甲基吗啉 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 16.17h， 生成 2-氨基-2-硫代乙基氨基甲酸叔丁酯
  参考文献：
  名称：

  一氧化氮捐赠者拉格唑前药的合成和抗增殖活性。

  摘要：

  海洋天然产物Largazole是迄今为止确定的最有效的I类HDAC抑制剂。自从发现以来，由于其区分肿瘤细胞和正常细胞的能力，许多研究小组被结构复杂性和独特的抗癌活性所吸引。在这里，我们讨论了作为双重HDAC抑制剂和一氧化氮（NO）供体的Largazole杂合类似物的合成及其体外生物学特性，它们可能用作抗癌剂。特别地，呈现了具有NO-供体功能的Largazole的经修饰的硫酯部分的代谢稳定性，NO的体外释放以及在肿瘤细胞系中的抗增殖活性。

  DOI：

  10.1021/acsmedchemlett.9b00643

文献信息

• HIV protease inhibiting compounds
  申请人：Flentge Charles A.

  公开号：US20110003827A1

  公开（公告）日：2011-01-06

  A compound of the formula is disclosed as an HIV protease inhibitor. Methods and compositions for inhibiting an HIV infection are also disclosed.

  公开了一种具有以下公式的化合物，作为HIV蛋白酶抑制剂。还公开了抑制HIV感染的方法和组合物。
• Highly Regioselective Synthesis of 1,3,5-Trisubstituted 1,2,4-Triazole Derivatives
  作者：David Ellis、Aurelio Arias-Wood

  DOI：10.1080/00397911.2010.525678

  日期：2011.5.3

  Abstract The synthesis of 1,3,5-trisubstituted-1,2,4-triazoles is described. The key reaction is the thermal cyclization of an amidrazone intermediate with the aminal of an aromatic aldehyde. The method allows a variety of functionalities to be incorporated to add diversity to the initial templates.

  摘要 描述了 1,3,5-三取代-1,2,4-三唑的合成。关键反应是脒腙中间体与芳香醛的缩醛胺的热环化。该方法允许结合各种功能以增加初始模板的多样性。
• Process Development and Scale-up Total Synthesis of Largazole, a Potent Class I Histone Deacetylase Inhibitor
  作者：Qi-Yin Chen、Pravin R. Chaturvedi、Hendrik Luesch

  DOI：10.1021/acs.oprd.7b00352

  日期：2018.2.16

  scale-up total synthesis of largazole, a potent class I selective histone deacetylase (HDAC) inhibitor, a potential anticancer agent and also useful for the treatment of other disorders where transcriptional reprogramming might be beneficial. The synthetic route and conditions for each fragment and final product were modified and optimized to make them suitable for larger-scale synthesis. With the

  在此，我们描述了拉格唑放大全合成工艺的研究和开发，拉格唑是一种有效的 I 类选择性组蛋白脱乙酰酶 (HDAC) 抑制剂，是一种潜在的抗癌药物，也可用于治疗转录重编程可能影响的其他疾病。有利。对每个片段和最终产物的合成路线和条件进行了修改和优化，使其适合大规模合成。通过我们开发的工艺，可以以良好到优异的产率合成数百克的每个片段和十克的最终产品拉格唑。根据最长序列，经过八个步骤，最终目标拉格唑的总产率为 21%，HPLC 纯度超过 95%。
• Radical-Mediated Thiol-Ene Strategy: Photoactivation of Thiol-Containing Drugs in Cancer Cells
  作者：Shuang Sun、Bruno L. Oliveira、Gonzalo Jiménez-Osés、Gonçalo J. L. Bernardes

  DOI：10.1002/anie.201811338

  日期：2018.11.26

  Photoactivated drugs provide an opportunity to improve efficacy alongside reducing side-effects in the treatment of severe diseases such as cancer. Described herein is a photoactivation decaging method of isobutylene-caged thiols through a UV-initiated thiol-ene reaction. The method was demonstrated with an isobutylene-caged cysteine, cyclic disulfide-peptide, and thiol-containing drug, all of which

  光活化药物为治疗癌症等严重疾病提供了提高疗效并减少副作用的机会。本文描述了通过UV引发的硫醇-烯反应对异丁烯笼蔽的硫醇进行光活化解笼的方法。该方法通过异丁烯笼住的半胱氨酸、环状二硫肽和含硫醇的药物进行了论证，所有这些药物在硫醇源和光引发剂存在下，在温和的紫外线照射下都能快速有效地释放。重要的是，研究表明组蛋白脱乙酰酶抑制剂拉格唑的活性在缝合时可以关闭，但在用非光毒性光照射时在癌细胞内选择性地打开。
• 3-pyrrolidinylthio-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
  申请人：Fujisawa Pharmaceutical Company, Ltd.

  公开号：US04921852A1

  公开（公告）日：1990-05-01

  3-Pyrrolidinylthio-1-azabicyclo [320] hept-2-ene-2-carboxylic acid anti-microbiotic compounds are prepared.

  3-吡咯烷硫基-1-氮杂双环[320]庚-2-烯-2-羧酸抗微生物化合物已经制备好。

表征谱图