3,4-二氢-2H-1,4-苯恶嗪-2-羧酸 | 90563-93-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 中文名称: 3,4-二氢-2H-1,4-苯恶嗪-2-羧酸
• 中文别名: 3,4-二氢-2H-1,4-苯并噁嗪-2-羧酸
• 英文名称: 3,4-dihydro-2H-benzo[b][1,4]oxazine-2-carboxylic acid
• 英文别名: 3,4-dihydro-2H-benzo[1,4]oxazine-2-carboxylic acid；(+/-)-3,4-dihydro-2H-benzo[b][1,4]oxazine-2-carboxylic acid；3,4-dihydro-2H-1,4-benzoxazine-2-carboxylic acid
• CAS: 90563-93-2
• 化学式: C₉H₉NO₃
• mdl: MFCD05865108
• 分子量: 179.175
• InChiKey: VNTNLTOJGXENIZ-UHFFFAOYSA-N

物化性质

• 熔点：
  175-177°
• 沸点：
  399.7±42.0 °C(Predicted)
• 密度：
  1.321±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2934999090

SDS

Name:	3 4-Dihydro-2H-1 4-benzoxazine-2-carboxylic acid Material Safety Data Sheet
Synonym:	None Known
CAS:	90563-93-2

Section 1 - Chemical Product MSDS Name:3 4-Dihydro-2H-1 4-benzoxazine-2-carboxylic acid Material Safety Data Sheet
Synonym:None Known

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
90563-93-2	3,4-Dihydro-2H-1,4-benzoxazine-2-carbo	97+	unlisted

Hazard Symbols: XI
Risk Phrases: 36/37/38

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Irritating to eyes, respiratory system and skin.
Potential Health Effects
Eye:
Causes eye irritation. May cause chemical conjunctivitis.
Skin:
Causes skin irritation.
Ingestion:
May cause irritation of the digestive tract.
Inhalation:
Causes respiratory tract irritation.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Immediately 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:
Get medical aid. Wash mouth out with 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:
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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
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. 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:
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation. Use with adequate ventilation. Wash clothing before reuse.
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:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 90563-93-2: 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 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: off-white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 130 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: C9H9NO3
Molecular Weight: 179.17

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Dust generation.
Incompatibilities with Other Materials:
Oxidizing agents, bases, amines.
Hazardous Decomposition Products:
Carbon monoxide, oxides of nitrogen, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 90563-93-2 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
3,4-Dihydro-2H-1,4-benzoxazine-2-carboxylic 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: XI
Risk Phrases:
R 36/37/38 Irritating to eyes, respiratory system
and skin.
Safety Phrases:
S 22 Do not breathe dust.
S 24/25 Avoid contact with skin and eyes.
S 26 In case of contact with eyes, rinse immediately
with plenty of water and seek medical advice.
S 36/37/39 Wear suitable protective clothing, gloves
and eye/face protection.
WGK (Water Danger/Protection)
CAS# 90563-93-2: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 90563-93-2 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 90563-93-2 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：

  3,4-二氢-2H-1,4-苯恶嗪-2-羧酸 在 三乙胺 作用下， 以 氯仿 为溶剂， 反应 12.08h， 生成 3,4-dihydro-2H-1,4-benzoxazin-2-yl-[4-(4-fluorophenyl)piperazin-1-yl]methanone
  参考文献：
  名称：

  New Substituted 1,4-Benzoxazine Derivatives with Potential Intracellular Calcium Activity

  摘要：

  Substituted 1,4-benzoxazines bearing an amino side chain at the 2-position were prepared and were found to have a moderate activity on intracellular calcium. Of the compounds studied it was found that those which possess a homoveratrylamino moiety exhibited superior potency. The chain length and the nature of the amine (4-fluorophenylpiperazine, 4-fluorobenzhydryloxyethylamine, N-substituted homoveratrylamine) is discussed. The 4-benzyl-3,4-dihydro-2[3-[[2-(3,4-dimethoxyphenyl)ethyl]amino]propyl]-2H-1,4-benzoxazine (3c) is the most potent derivative of the series with a ratio of IC50 values against PE (phenylephrine) and K+ of 2.1. Under these test conditions a ratio near 1 indicates potential intracellular calcium activity while a ratio greater than 100 an action on extracellular calcium influx.

  DOI：

  10.1021/jm970795t
• 作为产物：
  描述：

  3,4-二氢-2H-苯并[1,4]噁嗪-2-羧酸乙酯 在 lithium hydroxide monohydrate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 以93%的产率得到3,4-二氢-2H-1,4-苯恶嗪-2-羧酸
  参考文献：
  名称：

  Discovery of Dihydro-1,4-Benzoxazine Carboxamides as Potent and Highly Selective Inhibitors of Sirtuin-1

  摘要：

  DOI：

  10.1021/acs.jmedchem.1c00017

文献信息

• [EN] SUBSTITUTED CYCLOLAKYLS AS MODULATORS OF THE INTEGRATED STRESS PATHWAY<br/>[FR] CYCLOLALKYLES SUBSTITUÉS EN TANT QUE MODULATEURS DE LA VOIE DE STRESS INTÉGRÉE
  申请人：CALICO LIFE SCIENCES LLC

  公开号：WO2020223536A1

  公开（公告）日：2020-11-05

  Provided herein are compounds, compositions, and methods useful for modulating the integrated stress response (ISR) and for treating related diseases, disorders and conditions.

  本文提供了用于调节综合应激反应（ISR）并治疗相关疾病、疾病和症状的化合物、组合物和方法。
• [EN] GLYCINE B ANTAGONISTS<br/>[FR] ANTAGONISTES DE LA GLYCINE B
  申请人：MERZ PHARMA GMBH & CO KGAA

  公开号：WO2010139481A1

  公开（公告）日：2010-12-09

  The invention relates to naphthalene derivatives as well as their pharmaceutically acceptable salts. The invention further relates to a process for the preparation of such compounds. The compounds of the invention are glycine B antagonists and are therefore useful for the control and prevention of various disorders, including neurological disorders.

  该发明涉及萘衍生物以及它们的药用可接受盐。该发明还涉及一种制备这些化合物的方法。该发明的化合物是甘氨酸B拮抗剂，因此对于控制和预防各种疾病，包括神经系统疾病，具有用处。
• [EN] SUBSTITUTED 3-PIPERIDINYL-PYRROLO[2,3-B]PYRIDINES AND RELATED COMPOUNDS AND THEIR USE IN TREATING MEDICAL CONDITIONS<br/>[FR] 3-PIPÉRIDINYL-PYRROLO[2,3-B]PYRIDINES SUBSTITUÉES ET COMPOSÉS APPARENTÉS ET LEUR UTILISATION DANS LE TRAITEMENT D'ÉTATS MÉDICAUX
  申请人：IKENA ONCOLOGY INC

  公开号：WO2022051569A1

  公开（公告）日：2022-03-10

  The invention provides substituted 3-piperidinyl-pyrrolo[2,3-b]pyridines and related compounds, pharmaceutical compositions, their use for inhibiting ERK5 activity, and their use in the treatment of medical disorders, such as cancer.

  本发明提供了取代的3-哌啶基吡咯[2,3-b]吡啶和相关化合物、药物组合物，其用于抑制ERK5活性以及其在治疗医学疾病（如癌症）中的应用。
• Non-peptide gnrh antagonists
  申请人：Roe Bryan Michael

  公开号：US20050222139A1

  公开（公告）日：2005-10-06

  Compounds according to general formula 1, wherein A 1 -A 3 are selected from A 5 and A 6 where A 5 is either ═CR 13 — or ═N— and A 6 is —NR 14 —, —O— or —S—; A 4 is either a covalent bond or A 5 , provided that when A 4 is a covalent bond one of A 1 -A 3 must be A 6 and the other two must be A 5 and when A 4 is A 5 then all of A 1 -A 3 must be A 5 ; R 1 is selected from H, NHY′ and COY 2 , in which case R 2 is H, or R 1 and R2 may both be methyl or together represent ═O; R 3 , R 4 and R 5 are each independently selected from H and lower alkyl groups; R 6 , R 7 , R 8 , R 9 , R 10 , R 11 and R 12 are each independently selected from H, lower alkyl groups, NH 2 , halogens (F, CI and Br) O-alkyl, CH 2 NM 2 and CF 3 ; R 13 is selected from H, F, CI Br, NO 2 , NH 2 , OH, Me, Et, OMe, NMe 2 and CF 3 ; R 14 is selected from H, methyl and ethyl; W is selected from ═CH— and ═N—; X is selected from CH 2 , O, S, SO 2 , NH and N lower alkyl; Y 1 is selected from CO-lower alkyl, CO(CH 2 ) b Y 3 , CO(CH 2 ) b COY 3 and CO(CH)NHCOY 3 , where b is 1-3; Y2 is selected from OR 15 , NR 16 R 17 and NH(CH 2 ) C COY 3 , where c is 1-3; Y 3 is selected from OR 15 and NR 16 R 17 ; R 15 is selected from H, lower alkyl and (CH 2 ) a R 16 , where a is 0-4; R 16 and R 17 are each independently selected from H, lower alkyl and (CH 2 ) a R 16 or together are —(CH 2 ) 2 -Z-(CH 2)2 —; R 18 is OH a phenyl group or an aromatic heterocycle selected from pyridyl, pyrimidinyl, pyrazinyl, furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl and thiadiazolyl, each of which may optionally have a lower alkyl group substituent; and Z is selected from O, CH 2 , S, SO 2 , NH and N-lower alkyl, are new. They are useful in the treatment of breast and prostate cancer, endometriosis and benign prostate hyperplasia, in the regulation of fertility, and in in vitro fertilisation.

  化合物按照通式1进行选择，其中A1-A3选择自A5和A6，其中A5为═CR13—或═N—，A6为—NR14—，—O—或—S—；A4为共价键或A5，若A4为共价键，则A1-A3中必须有一个为A6，其余两个必须为A5，若A4为A5，则A1-A3全部必须为A5；R1选择自H、NHY′和COY2，此时R2为H，或者R1和R2都可以为甲基，或者一起代表═O；R3、R4和R5各自独立选择自H和较低的烷基基团；R6、R7、R8、R9、R10、R11和R12各自独立选择自H、较低的烷基基团、NH2、卤素（F、CI和Br）、O-烷基、CH2NM2和CF3；R13选择自H、F、CI、Br、NO2、NH2、OH、Me、Et、OMe、NMe2和CF3；R14选择自H、甲基和乙基；W选择自═CH—和═N—；X选择自CH2、O、S、SO2、NH和较低的烷基；Y1选择自CO-较低的烷基、CO(CH2)bY3、CO(CH2)bCOY3和CO(CH)NHCOY3，其中b为1-3；Y2选择自OR15、NR16R17和NH(CH2)CCOY3，其中c为1-3；Y3选择自OR15和NR16R17；R15选择自H、较低的烷基和(CH2)aR16，其中a为0-4；R16和R17各自独立选择自H、较低的烷基和(CH2)aR16，或者一起为—(CH2)2-Z-(CH2)2—；R18为OH、苯基或选择自吡啶基、嘧啶基、吡嗪基、呋喃基、噻吩基、吡咯基、咪唑基、吡唑基、噁唑基、异噁唑基、噻唑基、异噻唑基、三唑基、噁二唑基和噻二唑基的芳香杂环，每个都可以选择具有较低的烷基基团取代基；Z选择自O、CH2、S、SO2、NH和N-较低的烷基。它们在乳腺和前列腺癌、子宫内膜异位症和良性前列腺增生的治疗、生育调节以及体外受精方面有用。
• Non-peptide GnRH antagonists
  申请人：Roe Michael Bryan

  公开号：US20080255109A1

  公开（公告）日：2008-10-16

  Compounds according to general formula 1, wherein A 1 -A 3 are selected from A 5 and A 6 where A 5 is either ═CR 13 — or ═N— and A 6 is —NR 14 —, —O— or —S—; A 4 is either a covalent bond or A 5 , provided that when A 4 is a covalent bond one of A 1 -A 3 must be A 6 and the other two must be A 5 and when A 4 is A 5 then all of A 1 -A 3 must be A 5 ; R 1 is selected from H, NHY′ and COY 2 , in which case R 2 is H, or R 1 and R 2 may both be methyl or together represent ═O; R 3 , R 4 and R 5 are each independently selected from H and lower alkyl groups; R 6 , R 7 , R 8 , R 9 , R 10 , R 11 and R 12 are each independently selected from H, lower alkyl groups, NH 2 , halogens (F, Cl and Br) O-alkyl, CH 2 NM 2 and CF 3 ; R 13 is selected from H, F, Cl, Br, NO 2 , NH 2 , OH, Me, Et, OMe, NMe 2 and CF 3 ; R 14 is selected from H, methyl and ethyl; W is selected from ═CH— and ═N—; X is selected from CH 2 , O, S, SO 2 , NH and N-lower alkyl; Y 1 is selected from CO-lower alkyl, CO(CH 2 ) b Y 3 , CO(CH 2 ) b COY 3 and CO(CH 2 ) b NHCOY 3 , where b is 1-3; Y 2 is selected from OR 15 , NR 16 R 17 and NH(CH 2 ) c COY3, where c is 1-3; Y 3 is selected from OR 15 and NR 16 R 17 ; R 15 is selected from H, lower alkyl and (CH 2 ) a R 16 , where a is 0-4; R 16 and R 17 are each independently selected from H, lower alkyl and (CH 2 ) a R 16 or together are —(CH 2 ) 2 -Z-(CH 2 ) 2 —; R 18 is OH, a phenyl group or an aromatic heterocycle selected from pyridyl, pyrimidinyl, pyrazinyl, furyl, thienyl, pyrrolyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl and thiadiazolyl, each of which may optionally have a lower alkyl group substituent; and Z is selected from O, CH 2 , S, SO 2 , NH and N-lower alkyl, are new. They are useful in the treatment of breast and prostate cancer, endometriosis and benign prostate hyperplasia, in the regulation of fertility, and in in vitro fertilisation.

  化合物的一般式为1，其中A1-A3从A5和A6中选择，其中A5是═CR13—或═N—，A6是—NR14—，—O—或—S—; A4是共价键或A5，如果A4是共价键，则A1-A3中必须有一个为A6，另外两个必须为A5，如果A4是A5，则A1-A3必须全部为A5; R1从H，NHY'和COY2中选择，此时R2为H，或者R1和R2都可以是甲基或者一起表示为═O; R3，R4和R5各自独立选择自H和较低的烷基基团; R6，R7，R8，R9，R10，R11和R12各自独立选择自H，较低的烷基基团，NH2，卤素（F，Cl和Br），O-烷基，CH2NM2和CF3; R13从H，F，Cl，Br，NO2，NH2，OH，Me，Et，OMe，NMe2和CF3中选择; R14从H，甲基和乙基中选择; W从═CH—和═N—中选择; X从CH2，O，S，SO2，NH和N-较低的烷基中选择; Y1从CO-较低的烷基，CO(CH2)bY3，CO(CH2)bCOY3和CO(CH2)bNHCOY3中选择，其中b为1-3; Y2从OR15，NR16R17和NH(CH2)cCOY3中选择，其中c为1-3; Y3从OR15和NR16R17中选择; R15从H，较低的烷基和(CH2)aR16中选择，其中a为0-4; R16和R17各自独立选择自H，较低的烷基和(CH2)aR16，或者一起为—(CH2)2-Z-(CH2)2—; R18为OH，苯基或从吡啶基，嘧啶基，吡嗪基，呋喃基，噻吩基，吡咯基，咪唑基，吡唑基，噁唑基，异噁唑基，噻唑基，异噻唑基，三唑基，噁二唑基和噻二唑基中选择的芳香杂环，每个芳香杂环可以选择有较低的烷基基团取代物; Z从O，CH2，S，SO2，NH和N-较低的烷基中选择。它们在乳腺癌和前列腺癌，子宫内膜异位症和良性前列腺增生的治疗，调节生育能力以及体外受精方面有用。