(2Z)-{2-[(氯乙酰基)氨基]-1,3-噻唑-4-基}(甲氧基亚氨基)乙酸 | 64486-18-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: (2Z)-{2-[(氯乙酰基)氨基]-1,3-噻唑-4-基}(甲氧基亚氨基)乙酸
• 英文名称: 2-(2-chloroacetylaminothiazole-4-yl)-2-(Z)-methoxyiminoacetic acid
• 英文别名: 2-(2-chloroacetamido-4-thiazolyl)-2-(Z-methoxyimino)acetic acid；(2-chloroacetylamino-4-thiazolyl)-2-syn-methoxyiminoacetic acid；2-(2-chloroacetamido-4-thiazolyl)-2-methoxyimino-acetic acid；2-(2-chloroacetamidothiazol-4-yl)-2-methoxyiminoacetic acid；2-(2-chloroacetamidothiazol-4-yl)-2-(syn)-methoxyiminoacetic acid；α-(2-chloroacetamidothiazol-4-yl)-2-syn-α-methoxyiminoacetic acid；[2-(2-chloro-acetylamino)-thiazol-4-yl]-(Z)-methoxyimino-acetic acid；(Z)-2-(2-chloroacetylaminothiazol-4-yl)-2-methoxyiminoacetic acid；2-(2-chloroacetamido-4-thiazolyl)-2-syn-methoxyimino acetic acid；2-(2-chloroacetamidothiazole-4-yl)-2-syn-methoxyiminoacetic acid；2-(2-chloroacetylaminothiazol-4-yl)-2-syn-methoxyiminoacetic acid；(2Z)-{2-[(chloroacetyl)amino]-1,3-thiazol-4-yl}(methoxyimino)acetic acid；(2Z)-2-[2-[(2-chloroacetyl)amino]-1,3-thiazol-4-yl]-2-methoxyiminoacetic acid
• CAS: 64486-18-6
• 化学式: C₈H₈ClN₃O₄S
• mdl: MFCD00067025
• 分子量: 277.688
• InChiKey: JVFVSVLCXCDOPD-SDQBBNPISA-N

物化性质

• 熔点：
  164-166 °C
• 密度：
  1?+-.0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  129
• 氢给体数：
  2
• 氢受体数：
  7

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2934100090

SDS

Name:	(Z)-(2-(Chloroacetamido)thiazole-4-y)-methoxyiminoacetic acid 96% Material Safety Data Sheet
Synonym:	2-((Chloroacetyl)Amino)-Beta-Methoximino)-4-Thiazoleacetic Acid
CAS:	64486-18-6

Section 1 - Chemical Product MSDS Name:(Z)-(2-(Chloroacetamido)thiazole-4-y)-methoxyiminoacetic acid 96% Material Safety Data Sheet
Synonym:2-((Chloroacetyl)Amino)-Beta-Methoximino)-4-Thiazoleacetic Acid

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
64486-18-6	(Z)-(2-(Chloroacetamido)thiazole-4-y)-	96	264-916-4

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

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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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. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

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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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
In case of fire, use water, dry chemical, chemical foam, or alcohol-resistant foam. Use agent most appropriate to extinguish fire.

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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. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use process enclosure, local exhaust ventilation, or other engineering controls to control airborne levels.
Exposure Limits CAS# 64486-18-6: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to minimize contact with skin.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder
Color: slightly beige
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 166 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: 1.4 g/l (20c)
Specific Gravity/Density:
Molecular Formula: C8H8ClN3O4S
Molecular Weight: 277.64

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Hydrogen chloride, carbon monoxide, oxides of nitrogen, irritating and toxic fumes and gases, carbon dioxide, sulfur oxides (SOx), including sulfur oxide and sulfur dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 64486-18-6 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(Z)-(2-(Chloroacetamido)thiazole-4-y)-methoxyiminoacetic acid - 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
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
RID/ADR
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing group:

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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# 64486-18-6: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 64486-18-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 64486-18-6 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：

  (2Z)-{2-[(氯乙酰基)氨基]-1,3-噻唑-4-基}(甲氧基亚氨基)乙酸 生成 氨噻肟酸
  参考文献：
  名称：

  Method for removing protective groups

  摘要：

  通过将卤代乙酰氨基化合物与N-取代二硫代氨基甲酸或其盐反应，可以在短时间内将卤代乙酰基团从卤代乙酰氨基化合物中去除。

  公开号：

  US04251657A1
• 作为产物：
  描述：

  氨噻肟酸 以84.7%的产率得到(2Z)-{2-[(氯乙酰基)氨基]-1,3-噻唑-4-基}(甲氧基亚氨基)乙酸
  参考文献：
  名称：

  Process for producing chloroacetylaminothiazoleacetic acid derivatives

  摘要：

  公开号：

  EP0859002B1

文献信息

• Cephalosporin derivatives
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04380541A1

  公开（公告）日：1983-04-19

  Novel 7-[2-(2-aminothiazol-4-yl)-2-(syn)-methoxyiminoacetamido]cephalosporanic acid derivatives of the formula: ##STR1## wherein R.sup.1 NH is an amino group which may optionally be protected, R.sup.2 is a halogen atom or a hydroxyl, thiol or amino group which may optionally be substituted; COOR is a carboxyl group which may optionally be esterified, and pharmaceutically acceptable salts thereof, have excellent antimicrobial activity against a broad spectrum of microorganisms including Gram-negative bacteria such as Escherichia coli, Serratia marcescens, Proteus rettgeri, Enterobacter cloacae, Citrobacter freundii. Thus, these compounds may be used as antibacterial agents for therapeutic purposes.

  7- [2- (2-氨基噻唑-4-基)-2-(同)-甲氧基亚胺基乙酰头孢菌素酸衍生物的结构式为：##STR1##其中R.sup.1 NH为可能被保护的氨基团，R.sup.2为卤素原子或可选择被取代的羟基、硫醇或氨基团；COOR为可能被酯化的羧基，以及其药学上可接受的盐，对包括大肠杆菌、马克赛氏沙雷氏菌、雷特格氏变形杆菌、克洛阿克肠菌、弗伦德氏柠檬酸杆菌在内的广谱微生物具有出色的抗菌活性。因此，这些化合物可以用作治疗目的的抗菌剂。
• Synthesis and biological evaluation of optically active 3-H-1-carbacephem compounds.
  作者：Takehiro OGASA、Hiromitsu SAITO、Yukio HASHIMOTO、Kiyoshi SATO、Tadashi HIRATA

  DOI：10.1248/cpb.37.315

  日期：——

  Horner-Emmons cyclization. Optically active 3-H-1-carbacephem compounds were efficiently prepared by employing a penicillin acylase-producing microorganism in two ways. That is, the 7-phenylacetamide of a racemic carbacephem nucleus was hydrolyzed enantioselectively with the enzyme to afford the optically pure nucleus, which was then acylated to give antimicrobial compounds. Alternatively, a racemic

  通过2 + 2环加成，然后进行分子内Horner-Emmons环化，制备具有或不具有2个α-或2个β-甲基的3-H-1-Carbacephem核。通过以两种方式使用产生青霉素酰基转移酶的微生物，可以有效地制备旋光的3-H-1-卡巴西姆化合物。即，将外消旋羧苄核的7-苯基乙酰胺用该酶对映选择性地水解，得到光学纯的核，然后将其酰化，得到抗菌化合物。或者，用该酶直接和对映选择性地将消旋的羧苄基核苯基糖基化。3-H-1-Carbacephemem核似乎是青霉素酰基转移酶比天然来源的penam或cephem核更好的底物。3-H-1-Carbacephemem化合物显示出有效的抗菌活性；化合物32a显示出的活性与头孢唑肟相当，后者是具有相同酰基的头孢烯类似物。令人感兴趣的是，事实证明，3-H-1-碳环糊精化合物比其3-取代的甲基类似物具有更强的抗菌活性。
• 1-Sulfo-2-oxoazetidine derivatives and their production
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04550105A1

  公开（公告）日：1985-10-29

  Disclosed are compounds of the general formula: ##STR1## wherein R.sub.1 is amino, an acylated amino or a protected amino group, X is hydrogen or methoxy, and R' is hydrogen, R or R.sup.4 wherein R is an organic residue attached to the azetidine ring through a carbon atom therein and R.sub.4 is azido, a halogen, an amino group which may optionally be acylated or a group of the formula --OR.sub.5, ##STR2## or --S--S--R.sub.5 wherein R.sub.5 is an organic residue and n is 0, 1 or 2, and pharmaceutically acceptable salts and esters thereof. The compounds have antimicrobial and/or .beta.-lactamase-inhibitory activity and are of value as drugs for human beings and domesticated animals.

  揭示了一般式为：其中R₁为氨基、酰化氨基或保护氨基，X为氢或甲氧基，R'为氢、R或R⁴，其中R为有机残基，通过其中的碳原子连接到氮杂环上，R⁴为叠氮基、卤素、氨基（可选地酰化）或具有如下结构的基团--OR₅，或--S--S--R₅，其中R₅为有机残基，n为0、1或2，以及其药学上可接受的盐和酯。这些化合物具有抗微生物和/或β-内酰胺酶抑制活性，并且作为人类和驯养动物的药物具有价值。
• 1-sulfo-2-oxoazetidine derivatives and their production
  申请人：Takeda Chemical Industries, Ltd.

  公开号：US04782147A1

  公开（公告）日：1988-11-01

  Disclosed are compounds of the general formula: ##STR1## wherein R.sub.1 is amino, an acylated amino or a protected amino group, X is hydrogen or methoxy, and R' is hydrogen, R or R.sup.4 wherein R is an organic residue attached to the azetidine ring through a carbon atom therein and R.sub.4 is azido, a halogen, an amino group which may optionally be acylated or a group of the formula ##STR2## wherein R.sub.5 is an organic residue and n is 0, 1 or 2, and pharmaceutically acceptable salts and esters thereof. The compounds have antimicrobial and/or .beta.-lactamase-inhibitory activity and are of value as drugs for human beings and domesticated animals.

  揭示了一般式化合物：##STR1## 其中 R.sub.1 是氨基、酰化氨基或保护氨基，X 是氢或甲氧基，而 R' 是氢、R 或 R.sup.4，其中 R 是通过其中的一个碳原子连接到环的有机残基，而 R.sub.4 是偶氮基、卤素、氨基（可选地酰化）或式 ##STR2## 其中 R.sub.5 是有机残基，n 为 0、1 或 2，以及其药学上可接受的盐和酯。这些化合物具有抗微生物和/或β-内酰胺酶抑制活性，并且作为人类和驯化动物的药物具有价值。
• Synthesis of 4-(methoxyethyl) monobactams by a chemicoenzymatic approach.
  作者：HARUO YAMASHITA、NOBUYOSHI MINAMI、KYOICHI SAKAKIBARA、SUSUMU KOBAYASHI、MASAJI OHNO

  DOI：10.1248/cpb.36.469

  日期：——

  As a key intermediate for the synthesis of monobactam analogues, cis-3-benzyloxycarbonyl-amino-4-(2-hydroxyehtyl)-2-azetidinone was synthesized from (4S)-4-methoxycarbonylmethyl-2-azetidinone, and converted into monobactams having a methoxyethyl group at the C-4 position of the β-lactam ring. Among the compounds synthesized, disodium (3S, 4R)-3[2-(2-aminothiazol-4-yl)-(Z)-2-carboxymethoxyiminoacetamido]-4-(2-methoxyethyl)-2-azetidinone-1-sulfonate showed strong activity against a variety of gram-negative bacteria except Pseudomonas aeruginosa. Furthemore, the 4-methoxyethyl derivatives exhibited excellent stabiliy to β-lactamases, and the syntheses of the corresponding trans isomer and 3α-methoxy derivatives are also described.

  作为合成单环β内酰胺类似物的关键中间体，顺-3-苄氧基羰基氨基-4-(2-羟乙基)-2-氮杂环丁酮是由(4S)-4-甲氧基羰基甲基-2-氮杂环丁酮合成的，并转化为在β-内酰胺环C-4位具有甲氧乙基基团的单环β内酰胺。在合成的化合物中，双钠盐(3S, 4R)-3[2-(2-氨基噻唑-4-基)-(Z)-2-羧基甲氧基亚胺乙酰氨基]-4-(2-甲氧乙基)-2-氮杂环丁酮-1-磺酸盐对多种革兰阴性细菌表现出强活性，除了铜绿假单胞菌。此外，4-甲氧乙基衍生物对β-内酰胺酶显示出优异的稳定性，并且相应的反式异构体和3α-甲氧基衍生物的合成也被描述。