3,4-二氢-2H-1,4-苯并恶嗪-2-甲醇 | 82756-74-9

• 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-苯并恶嗪-2-甲醇
• 中文别名: 3,4-二氢-2H-1,4-苯并噁嗪-2-甲醇
• 英文名称: (3,4-dihydro-2H-1,4-benzoxazine-2-yl)methanol
• 英文别名: 3,4-Dihydro-2H-1,4-benzoxazin-2-ylmethanol；2-hydroxymethyl-benzomorpholine；2-Hydroxymethyl-benzomorpholin；(3,4-dihydro-2H-benzo[1,4]oxazin-2-yl)-methanol；4H-2,3-dihydro-2-hydroxymethyl-1,4-benzoxazine
• CAS: 82756-74-9
• 化学式: C₉H₁₁NO₂
• mdl: MFCD06200861
• 分子量: 165.192
• InChiKey: HDDDVYQKGVCTRM-UHFFFAOYSA-N

物化性质

• 沸点：
  143-145 °C(Press: 0.15 Torr)
• 密度：
  1.164±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  41.5
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

SDS

Name:	3 4-Dihydro-2H-1 4-benzoxazin-2-ylmethanol Material Safety Data Sheet
Synonym:	None Known
CAS:	82756-74-9

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

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
82756-74-9	3,4-Dihydro-2H-1,4-benzoxazin-2-ylmeth	97+	unlisted

Hazard Symbols: C
Risk Phrases: 34

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Causes burns.
Potential Health Effects
Eye:
Causes eye burns.
Skin:
Causes skin burns.
Ingestion:
Causes gastrointestinal tract burns.
Inhalation:
Causes chemical burns to the respiratory tract.
Chronic:
Chronic exposure may cause effects similar to those of acute exposure.

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Section 4 - FIRST AID MEASURES
Eyes: In case of contact, immediately flush eyes with plenty of water for at least 15 minutes. Get medical aid immediately.
Skin:
In case of contact, immediately flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Get medical aid immediately. Wash clothing before reuse.
Ingestion:
If swallowed, do NOT induce vomiting. Get medical aid immediately.
If victim is fully conscious, give a cupful of water. Never give anything by mouth to an unconscious person.
Inhalation:
Get medical aid immediately. Remove from exposure and move to fresh air immediately. If breathing is difficult, give oxygen. Do NOT use mouth-to-mouth resuscitation. If breathing has ceased apply artificial respiration using oxygen and a suitable mechanical device such as a bag and a mask.
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.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions. Provide ventilation. Vacuum or sweep up material and place into a suitable, dry disposal container.

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Section 7 - HANDLING and STORAGE
Handling:
Minimize dust generation and accumulation. Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing.
Keep container tightly closed. Do not ingest or inhale. Discard contaminated shoes. Use only with adequate ventilation.
Storage:
Keep container closed when not in use. Store under an inert atmosphere. Store in a cool, dry 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 adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 82756-74-9: 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:
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: Solid
Color: brown
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
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: C9H11NO2
Molecular Weight: 165.20

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions. Low melting point solid.
Conditions to Avoid:
Dust generation.
Incompatibilities with Other Materials:
Oxidizing agents, acids, halogenated agents, halogens, acid chlorides.
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# 82756-74-9 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
3,4-Dihydro-2H-1,4-benzoxazin-2-ylmethanol - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: Pseudomonas putida:

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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: AMINES SOLID, COROSIVE, N.O.S.
Hazard Class: 8
UN Number: 3259
Packing Group: III
IMO
Shipping Name: AMINES SOLID, COROSIVE, N.O.S.
Hazard Class: 8
UN Number: 3259
Packing Group: III
RID/ADR
Shipping Name: AMINES SOLID, COROSIVE, N.O.S.
Hazard Class: 8
UN Number: 3259
Packing group: III

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: C
Risk Phrases:
R 34 Causes burns.
Safety Phrases:
S 23 Do not inhale gas/fumes/vapour/spray.
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.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 82756-74-9: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 82756-74-9 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 82756-74-9 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-苯并恶嗪-2-甲醇 在 吡啶 、 sodium azide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-[(3-1H-Indol-3-yl-propionylamino)-methyl]-2,3-dihydro-benzo[1,4]oxazine-4-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Studies toward the discovery of the next generation of antidepressants. Part 5: 3,4-Dihydro-2H-benzo[1,4]oxazine derivatives with dual 5-HT1A receptor and serotonin transporter affinity

  摘要：

  The design, synthesis, and structure-activity relationship of two novel classes of benzoxazine derivatives with dual selective serotonin reuptake inhibitors and 5-HT1A receptor activities are described. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.11.054
• 作为产物：
  描述：

  4-乙酰基-3,4-二氢-2H-1,4-苯并噁嗪-2-羧酸甲酯 在 红铝 作用下， 以 甲苯 为溶剂， 反应 1.17h， 以100%的产率得到3,4-二氢-2H-1,4-苯并恶嗪-2-甲醇
  参考文献：
  名称：

  1,4-恶嗪化学研究，2-取代二氢-1,4-苯并恶嗪化学第5部分1

  摘要：

  使用 LiAlH4 将 4 还原为 6、7 和 8，使用 NaBH4/LiCl 还原为 8 和 9，使用 Redal® 还原为 7。通过对 11 和 13 的比较研究阐明了 7 的形成。5 和 17 使用 LiAlH4 产生 16，而使用 Redal®/吗啉的 17 不产生醛 19a 而是 18。19a 与来自 4 的水合物 19b 与 Redal?/吗啉形成混合物。

  DOI：

  10.1002/ardp.19823150611

文献信息

• A metal catalyst-free and one-pot synthesis of (3,4-dihydro-2H-benzo[b][1,4]oxazin-2-yl)methanol derivatives in water
  作者：Shambhu Nath Singh、Sarva Jayaprakash、K. Venkateshwara Reddy、Ali Nakhi、Manojit Pal

  DOI：10.1039/c5ra14478g

  日期：——

  Regioselective synthesis of (3,4-dihydro-2H-benzo[b][1,4]oxazin-2-yl)methanols have been accomplished via a greener method.

  区域选择性的合成(3,4-二氢-2H-苯并[b][1,4]恶嗪-2-基)甲醇已经通过一种更环保的方法完成。
• Discovery of a new class of potent, selective, and orally active prostaglandin D2 receptor antagonists
  作者：Kazuhiko Torisu、Kaoru Kobayashi、Maki Iwahashi、Yoshihiko Nakai、Takahiro Onoda、Toshihiko Nagase、Isamu Sugimoto、Yutaka Okada、Ryoji Matsumoto、Fumio Nanbu、Shuichi Ohuchida、Hisao Nakai、Masaaki Toda

  DOI：10.1016/j.bmc.2004.07.048

  日期：2004.10

  acetic acid analogs is presented since these compounds represent a new class of potent, selective, and orally active prostaglandin D2 (PGD2) receptor antagonists. Most of these compounds exhibit strong PGD2 receptor binding and PGD2 receptor antagonism in cAMP formation assays. When given orally, these new antagonists dramatically suppress allergic inflammatory responses, such as the PGD2-induced or

  提出了发现一系列N-（对烷氧基）苯甲酰基-2-甲基吲哚-4-乙酸类似物的过程，因为这些化合物代表了一类新的强效，选择性和口服活性前列腺素D2（PGD2）受体拮抗剂。这些化合物大多数在cAMP形成分析中表现出较强的PGD2受体结合和PGD2受体拮抗作用。口服时，这些新的拮抗剂可显着抑制过敏性炎症反应，例如PGD2诱导或OVA诱导的血管通透性增加。还讨论了结构活动关系（SAR）数据。
• A straightforward route to 4<i>H</i>-1,4-Benzoxazine-2-carbaldehydes by swern oxidation
  作者：Anne-Sophie Bourlot、Gérald Guillaumet、Jean-Yves Mérour

  DOI：10.1002/jhet.5570330133

  日期：1996.1

  Swern oxidation of saturated (1,4-benzoxazine-2-yl)-methanols 2 furnished 4H-1,4-benzoxazine-2-carbaldehydes 3, which possess an α,β ethylenic bond. The reactivity of these compounds was examined.

  饱和（1,4-苯并恶嗪-2-基）-甲醇2的剧烈氧化提供4 H -1,4-苯并恶嗪-2-甲醛3，它们具有α，β烯键。检查了这些化合物的反应性。
• 2,6-Difluorobenzamide Inhibitors of Bacterial Cell Division Protein FtsZ: Design, Synthesis, and Structure-Activity Relationships
  作者：Valentina Straniero、Carlo Zanotto、Letizia Straniero、Andrea Casiraghi、Stefano Duga、Antonia Radaelli、Carlo De Giuli Morghen、Ermanno Valoti

  DOI：10.1002/cmdc.201700201

  日期：2017.8.22

  filamentous temperature-sensitive Z (FtsZ) has emerged as a possible target, thanks to its ubiquitous expression and its homology to eukaryotic β-tubulin. In the latest years, several compounds were shown to interact with this prokaryotic protein and selectively inhibit bacterial cell division. Recently, our research group developed interesting derivatives displaying good antibacterial activities against

  各种耐药微生物不断涌现，限制了常见细菌感染的治疗选择。原本有效的抗菌剂由于对这些抗药性细菌的活性弱或无效而不再有用。此外，最近批准的抗生素均未影响创新目标，因此需要具有创新抗菌作用机制的新型药物。由于其普遍存在的表达及其与真核β-微管蛋白的同源性，必需的细胞分裂蛋白丝状温度敏感Z（FtsZ）已成为可能的靶标。在最近几年中，几种化合物显示出与该原核蛋白相互作用并选择性抑制细菌细胞分裂。最近，我们的研究小组开发了有趣的衍生物，它们对耐甲氧西林的金黄色葡萄球菌，耐万古霉素的粪肠球菌和结核分枝杆菌具有良好的抗菌活性。本研究的目的是总结不同取代的杂环的结构-活性关系，这些杂环通过亚甲基氧桥连接到2,6-二氟苯甲酰胺，并验证FtsZ作为此类抗菌剂的真正目标。
• CERTAIN ARYLALIPHATIC AND HETEROARYL-ALIPHATIC PIPERAZINYL PYRAZINES AND THEIR USE IN THE TREATMENT OF SEROTONIN-RELATED DISEASES
  申请人：Biovitrum, AB, a Stockholm, Sweden corporation

  公开号：US20040242554A1

  公开（公告）日：2004-12-02

  The invention relates to compounds of the general formula (I): 1 wherein Ar is optionally substituted aryl or heteroaryl; A is (i) —O—, —S—, —SO 2 —, —NH—, (ii) a C 1-4 -alkyl- or C 1-6 -acyl-substituted nitrogen atom or (iii) a C 1-8 -alkylene chain or a heteroalkylene chain having 2 to 8 chain atoms, which optionally contains at least one unsaturation, and which may be substituted and/or contain a bridge to form a saturated or partially or fully unsaturated ring having 3-8 ring members; B is —C(R 4 )(R 5 )—, —OC(R 4 )(R 5 )—, —N(R 6 )C(R 4 )(R 5 )—, —N(R 6 )—, —O—, —S— or —SO 2 —; R is optionally substituted C 3-8 -cycloalkyl, aryl or heteroaryl; R 1 is (i) a saturated or unsaturated azacyclic or aminoazacyclic ring, or a saturated diazacyclic or aminodiazacyclic ring, which has 4 to 7 ring members, or a saturated aminoazabicyclic, azabicyclic or diazabicyclic ring which has 7 to 10 ring members, which rings optionally are substituted in one or more positions, or a group —[C(R 4 )(R 5 )] x N(R 2a )(R 3a )]; R 2a , R 3a , R 4 , R 5 , R 6 and x are as defined in the claims, and n is 0 or 1; and pharmaceutically acceptable salts, hydrates and prodrug forms thereof. The compounds may be prepared by per se conventional methods and can be used for treating a human or animal subject suffering from a serotonin-related disorder, such as eating disorders, especially obesity, memory, disorders, schizophrenia, mood disorders, anxiety disorders, pain, sexual dysfunctions, and urinary disorders. The invention also relates to such use as well as to pharmaceutical compositions comprising a compound of formula (I).

  本发明涉及通式（I）的化合物：其中Ar是可选取代的芳基或杂芳基；A是（i）—O—，—S—，—SO2—，—NH—，（ii）C1-4烷基或C1-6酰基取代的氮原子，或（iii）C1-8烷基链或具有2-8链原子的杂烷基链，其可选包含至少一个不饱和度，并且可以取代和/或含有桥接以形成具有3-8环成员的饱和或部分或完全不饱和环；B是—C（R4）（R5）—，—OC（R4）（R5）—，—N（R6）C（R4）（R5）—，—N（R6）—，—O—，—S—或—SO2—；R是可选取代的C3-8环烷基，芳基或杂芳基；R1是（i）饱和或不饱和的氮杂环或氨基氮杂环，或饱和的二氮杂环或氨基二氮杂环，其具有4-7环成员，或饱和的氨基氮杂双环、氮杂双环或二氮杂双环，其具有7-10环成员，这些环在一个或多个位置上可选取代，或者是一个组—[C（R4）（R5）]xN（R2a）（R3a）；R2a，R3a，R4，R5，R6和x如权利要求中所定义，n为0或1；以及其药学上可接受的盐、水合物和前药形式。这些化合物可以通过常规方法制备，并可用于治疗患有血清素相关疾病的人或动物，例如进食障碍，尤其是肥胖症，记忆障碍，精神分裂症，情绪障碍，焦虑障碍，疼痛，性功能障碍和泌尿系统疾病。本发明还涉及这种用途以及包含通式（I）化合物的制药组合物。