1,2,3-噻重氮-4-羧酸乙酯 | 3989-36-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1,2,3-噻重氮-4-羧酸乙酯
• 中文别名: 1,2,3-噻二唑-4-羧酸乙酯
• 英文名称: ethyl 1,2,3-thiadiazole-4-carboxylate
• 英文别名: ethyl thiadiazole-4-carboxylate
• CAS: 3989-36-4
• 化学式: C₅H₆N₂O₂S
• 分子量: 158.181
• InChiKey: FBUHTNOJXVICFM-UHFFFAOYSA-N

物化性质

• 熔点：
  80 °C
• 沸点：
  231℃
• 密度：
  1.320
• 闪点：
  94℃
• 稳定性/保质期：
  按规定使用不会分解，避免氧化剂。

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  5

安全信息

• 安全说明：
  S24/25
• 海关编码：
  2934999090
• 包装等级：
  III
• 危险类别：
  6.1
• 危险品运输编号：
  UN3283
• 储存条件：
  存放于密闭、阴凉、干燥处

SDS

Name:	Ethyl 1 2 3-thiadiazole-4-carboxylate 97% Material Safety Data Sheet
Synonym:
CAS:	3989-36-4

Section 1 - Chemical Product MSDS Name:Ethyl 1 2 3-thiadiazole-4-carboxylate 97% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
3989-36-4	Ethyl 1,2,3-thiadiazole-4-carboxylate	97%	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately.
Notes to Physician:
Treat symptomatically and supportively.

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 3989-36-4: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: cream
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 83 - 84 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C5H6N2O2S
Molecular Weight: 158

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Nitrogen oxides, carbon monoxide, oxides of sulfur, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 3989-36-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Ethyl 1,2,3-thiadiazole-4-carboxylate - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
No information available.
IMO
No information available.
RID/ADR
No information available.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 3989-36-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 3989-36-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 3989-36-4 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  1,2,3-噻重氮-4-羧酸乙酯 在 水 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以38%的产率得到1,2,3-噻重氮-4-羧酸
  参考文献：
  名称：

  抑制不必要的细菌靶标：一种新型丝氨酸O-乙酰基转移酶抑制剂的发现。

  摘要：

  在β-变形杆菌和放线菌中，半胱氨酸生物合成酶在持久性过程中是必不可少的，而在生长或急性感染时则是必不可少的。在哺乳动物中不存在将无机硫转化为半胱氨酸所需的生物合成机制。因此，它是合适的药物靶标。我们寻找沙门氏菌丝氨酸乙酰转移酶（SAT）的抑制剂，该酶催化L-半胱氨酸生物合成的限速步骤。对三个包含91 243种化合物的ChemDiv聚焦库进行了虚拟筛选，以鉴定潜在的SAT抑制剂。支架相似性和整体理化性质分析允许选择购买的73种化合物，并在重组酶上进行评估。六种化合物的IC50 <

  DOI：

  10.1021/acsmedchemlett.9b00627
• 作为产物：
  描述：

  Methyl 2-(1-ethoxy-1-oxopropan-2-ylidene)hydrazine-1-carboxylate 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 生成 1,2,3-噻重氮-4-羧酸乙酯
  参考文献：
  名称：

  来自1,2,3-噻二唑的铑噻吩乙烯基苯使模块化合成多取代的噻吩成为可能

  摘要：

  描述了1,2,3-噻二唑与炔烃之间的铑催化的过环反应，该反应是通过以前未知的Rh噻吩基卡宾的中间体进行的，可进行高效且区域选择性的合成，直至完全取代的噻吩。

  DOI：

  10.1021/acs.orglett.6b00541

文献信息

• Carbapenem antibiotics
  申请人：Bristol-Myers Company

  公开号：US04644061A1

  公开（公告）日：1987-02-17

  Disclosed are novel carbapenem derivatives characterized by a 2-substituent of the formula ##STR1## in which A represents a C.sub.1 -C.sub.6 straight or branched chain alkylene group; R.sup.5 represents an optionally substituted aliphatic, cycloaliphatic, cycloaliphatic-aliphatic, aryl, araliphatic, heteroaryl, heteroaraliphatic, heterocyclyl or heterocyclyl-aliphatic radial and ##STR2## represents a nitrogen-containing aromatic heterocycle attached to the alkylene group A at a ring carbon atom and quaternized by substituent R.sup.5. Such derivatives are useful as potent antibacterial agents.

  公开了新型的碳青霉烯衍生物，其特征在于2-取代基的公式为##STR1##，其中A代表C.sub.1-C.sub.6的直链或支链亚烷基；R.sup.5代表可选地取代的脂肪族、环脂肪族、环脂肪族-脂肪族、芳香族、芳脂肪族、杂芳族、杂芳脂肪族、杂环基或杂环基-脂肪族基团；而##STR2##代表一个含氮的芳香杂环，通过亚烷基A与环上的碳原子相连，并通过取代基R.sup.5进行季铵化。这样的衍生物作为强效的抗菌剂是有用的。
• Stereochemistry and mechanistic insights in the [2^t + 2ⁱ + 2ⁱ] annulations of thioketenes and imines
  作者：Wei He、Junpeng Zhuang、Hongguang Du、Zhanhui Yang、Jiaxi Xu

  DOI：10.1039/c7ob02212c

  日期：——

  [2t + 2i + 2i] annulations of thioketenes and imines on the basis of experimental and computational investigations. In the [2t + 2i + 2i] annulations involving cyclic imines, the zwitterionic intermediates generated from monosubstituted thioketenes and the cyclic imines undergo a stepwise nucleophilic endo-addition/Si-face attack pathway with a second imines molecule, giving initially (2,4)-cis-(4,5)-cis-[2t

  在实验和计算研究的基础上，提出了[2 t + 2 i + 2 i ]硫代酮和亚胺环化的立体化学模型和机理见解。在涉及环亚胺的[2 t + 2 i + 2 i ]环中，由单取代硫代乙烯酮和环亚胺生成的两性离子中间体通过第二亚胺分子经历逐步的亲核内加成/ Si面攻击路径，最初为（ 2,4）-顺式-（4,5）-顺式-[2 t + 2 i + 2 i]年环，在碱性反应条件下可完全游离为相应的（2,4）-顺式-（4,5）-反式环化产物。硫代-施陶丁格环加成的环选择性取决于硫代烯酮和亚胺的取代基。比较了施陶丁格，硫代施陶丁格和磺胺施陶丁格中间体的反应性和环选择性。
• 一种铜催化1,2,3-硫二唑化合物与胺合成硫代酰胺化合物的方法
  申请人：华南理工大学

  公开号：CN112778067B

  公开（公告）日：2022-05-24

  本发明属于有机化学的技术领域，公开了一种铜催化1,2,3‑硫二唑化合物与胺合成硫代酰胺化合物的方法。方法为在保护性氛围下，以有机溶剂为反应介质，将1,2,3‑硫二唑化合物与胺类化合物在铜盐催化剂或铜催化剂和膦配体的作用下反应，后续处理，获得硫代酰胺化合物。本发明的方法以铜盐为催化剂，并采用膦配体，产率较高、底物适用性广。此外，该反应以1,2,3‑硫二唑化合物和胺类化合物为原料，具有原料廉价易制备、操作简便、原子经济性高的优点。
• 12,13-Aziridinyl Epothilones. Stereoselective Synthesis of Trisubstituted Olefinic Bonds from Methyl Ketones and Heteroaromatic Phosphonates and Design, Synthesis, and Biological Evaluation of Potent Antitumor Agents
  作者：K. C. Nicolaou、Derek Rhoades、Yanping Wang、Ruoli Bai、Ernest Hamel、Monette Aujay、Joseph Sandoval、Julia Gavrilyuk

  DOI：10.1021/jacs.7b02655

  日期：2017.5.31

  The synthesis and biological evaluation of a series of 12,13-aziridinyl epothilone B analogues is described. These compounds were accessed by a practical, general process that involved a 12,13-olefinic methyl ketone as a starting material obtained by ozonolytic cleavage of epothilone B followed by tungsten-induced deoxygenation of the epoxide moiety. The attachment of the aziridine structural motif

  描述了一系列 12,13-氮丙啶埃坡霉素 B 类似物的合成和生物学评价。这些化合物是通过一种实用的通用方法获得的，该方法涉及以 12,13-烯属甲基酮作为起始材料，通过臭氧分解埃坡霉素 B 然后钨诱导的环氧化物部分脱氧获得。氮丙啶结构基序的连接是通过应用 Ess-Kürti-Falck 氮丙啶化来实现的，而杂环侧链则是通过基于立体选择性膦酸酯的烯化作用引入的。为了确保后一种富电子杂环反应的高 (E) 选择性，有必要对古老的 Horner-Wadsworth-Emmons 反应进行前所未有的改进，使用 2-氟乙氧基膦酸酯，可能被证明在有机合成中具有普遍价值。这些研究导致发现了迄今为止报道的一些最有效的埃坡霉素。配备了适应现代药物递送技术的官能团，这些化合物中的一些表现出皮摩尔的效力，使它们成为抗体药物偶联物 (ADC) 的有效载荷，而其中一些化合物显示出令人印象深刻的抗耐药性人类癌细胞的活性，使其成为理想潜在的医疗应用。
• [EN] AZIRIDINE CONTAINING EPOTHILONE ANALOGS, METHODS OF SYNTHESIS, METHODS OF TREATMENT, AND DRUG CONJUGATES<br/>[FR] ANALOGUES D'ÉPOTHILONE CONTENANT DE L'AZIRIDINE, PROCÉDÉS DE SYNTHÈSE, MÉTHODES DE TRAITEMENT, ET CONJUGUÉS MÉDICAMENTEUX DE CEUX-CI
  申请人：UNIV RICE WILLIAM M

  公开号：WO2018191394A1

  公开（公告）日：2018-10-18

  In one aspect, the present disclosure provides epothilone analogs of the formula: (I) wherein the variables are as defined herein. In another aspect, the present disclosure also provides methods of preparing the compounds disclosed herein. In another aspect, the present disclosure also provides pharmaceutical compositions and methods of use of the compounds disclosed herein. Additionally, drug conjugates with cell targeting moieties of the compounds are also provided.

  在一个方面，本公开提供了公式为：(I)的紫杉醇类似物，其中变量如本文所定义。在另一个方面，本公开还提供了制备本文所披露化合物的方法。在另一个方面，本公开还提供了药物组合物和使用本文所披露化合物的方法。此外，还提供了具有细胞靶向基团的药物偶联物。