O-[2-(乙烯氧基)乙基]羟胺 | 391212-29-6

• 物质功能分类: 医药中间体
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: O-[2-(乙烯氧基)乙基]羟胺
• 中文别名: 1-[2-(氨基氧基)乙氧基]乙烯
• 英文名称: O-(2-vinyloxyethyl)hydroxylamine
• 英文别名: 1-[2-(aminooxy)ethoxy]ethylene；O-(2-(Vinyloxy)ethyl)hydroxylamine；O-(2-ethenoxyethyl)hydroxylamine
• CAS: 391212-29-6
• 化学式: C₄H₉NO₂
• mdl: MFCD09951926
• 分子量: 103.121
• InChiKey: XZTSFVPMMQNIAJ-UHFFFAOYSA-N

物化性质

• 沸点：
  60-65 °C(Press: 20 Torr)
• 密度：
  0.972

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  7
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: O-(2-(Vinyloxy)ethyl)hydroxylamine
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: O-(2-(Vinyloxy)ethyl)hydroxylamine
CAS number: 391212-29-6

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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: C4H9NO2
Molecular weight: 103.1

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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.

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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

制备方法与用途

应用

1-[(2-(氨基氧基)乙氧基]乙烯是一种有机合成中间体和医药中间体，在实验室研发过程和化工医药合成中均有应用。

制备 步骤A：2-（2-（乙烯基氧基）乙氧基）异吲哚啉-1,3-二酮的制备

向含有2-(乙烯基氧基)乙醇(20.4 mL，227 mmol)、三苯膦(59.5 g，227 mmol)和N-羟基邻苯二甲酰亚胺(37.0 g，227 mmol)的四氢呋喃(THF, 450 mL)溶液中加入DEAD (35.9 mL)，在氮气氛围下于0℃搅拌。16小时后，在室温下将反应混合物真空浓缩。过滤残留物，并用氯仿洗涤，随后再次进行真空浓缩。最终通过硅胶柱色谱(己烷∶乙酸乙酯=2∶1)纯化，得到黄色固体产物2-（2-（乙烯基氧基）乙氧基）异吲哚啉-1,3-二酮 (32.5 g, 61.4%)。

步骤B：O-(2-（乙烯基氧基）乙基)羟胺的制备

在四氯甲烷(DCM, 96 mL)中溶解2-（2-（乙烯基氧基）乙氧基）异吲哚啉-1,3-二酮 (32.0 g，137 mmol)，并向其中逐滴加入含有甲基肼(15.8 mL，137 mmol)的水溶液。在室温下搅拌1小时后，将所得悬浮液用乙醚稀释并过滤。滤液真空浓缩后，通过硅胶柱色谱法(己烷∶乙酸乙酯=3∶2至1∶1)纯化，得到黄色油状产物O-(2-（乙烯基氧基）乙基)羟胺 (10.7 g, 76%)。

反应信息

• 作为反应物：
  描述：

  O-[2-(乙烯氧基)乙基]羟胺 在 N,N-二甲基甲酰胺 草酰氯 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 19.0h， 以18%的产率得到3-(2-fluoro-4-methylsulfanyl-phenylamino)-thieno[3,2-c]pyridine-2-carboxylic acid (2-vinyloxy-ethoxy)-amide
  参考文献：
  名称：

  WO2008/24724

  摘要：

  公开号：
• 作为产物：
  描述：

  2-[2-(乙烯基氧基)乙氧基]异吲哚啉-1,3-二酮 在 甲基肼 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.0h， 以76%的产率得到O-[2-(乙烯氧基)乙基]羟胺
  参考文献：
  名称：

  HETEROCYCLIC COMPOUNDS AS MEK INHIBITORS

  摘要：

  该发明提供了由化学式I和化学式II表示的新型取代杂环化合物，或其药学上可接受的盐、溶剂合物、多型体、酯、互变异构体或前药，以及包含这些化合物的组合物。所提供的化合物可用作MEK的抑制剂，并且在治疗炎症性疾病、癌症和其他过度增殖性疾病方面具有用途。该发明还提供了一种治疗哺乳动物，特别是人类的炎症性疾病、癌症和其他过度增殖性疾病的方法。

  公开号：

  US20120238599A1
• 作为试剂：
  描述：

  O-[2-(乙烯氧基)乙基]羟胺 、 5-((4-溴-2-氯苯基)氨基)-4-氟-1-甲基-1H-苯并[d]咪唑-6-羧酸 在 O-[2-(乙烯氧基)乙基]羟胺 作用下， 以90的产率得到5-((4-溴-2-氯苯基)氨基)-4-氟-1-甲基-n-(2-(乙烯基氧基)乙氧基)-1H-苯并[d]咪唑-6-羧酰胺
  参考文献：
  名称：

  [EN] N3 ALKYLATED BENZIMIDAZOLE DERIVATIVES AS MEK INHIBITORS
  [FR] UTILISATION DE DERIVES DE BENZIMIDAZOLE ALKYLES N3 EN TANT QU'INHIBITEURS DE MEK

  摘要：

  本发明涉及公式I的化合物及其药学上可接受的盐和前药，其中W、R1、R2、R7、R8、R9和R10如规范中所定义。这些化合物是MEK抑制剂，对哺乳动物的高增殖性疾病，如癌症和炎症的治疗有用。本发明还涉及使用这些化合物治疗哺乳动物的高增殖性疾病的方法，以及包含这些化合物的制药组合物。

  公开号：

  WO2003077914A1

文献信息

• Heterocyclic Compounds as MEK Inhibitors
  申请人：Chikkanna Dinesh

  公开号：US20090275606A1

  公开（公告）日：2009-11-05

  The present invention relates to compounds of formula I and pharmaceutically acceptable salts. These compounds can act as potential MEK inhibitors in the treatment of hyperproliferative diseases, like cancer and inflammation. The present invention also reveals methods of preparation thereof.

  本发明涉及公式I的化合物和药用盐。这些化合物可以作为潜在的MEK抑制剂，用于治疗癌症和炎症等过度增殖性疾病。本发明还揭示了其制备方法。
• [EN] TOPICAL FORMULATIONS<br/>[FR] FORMULATIONS TOPIQUES
  申请人：NFLECTION THERAPEUTICS INC

  公开号：WO2020106304A1

  公开（公告）日：2020-05-28

  Provided herein are gelled topical formulations for the treatment of skin diseases comprising: a) a MEK inhibitor; b) one or more organic solvents in an amount of about 70% to about 99% by weight; and c) a gelling agent; wherein the one or more organic solvents are selected from the group consisting of C2-6 alcohol, a C2-6 alkylene glycol, a di-(C2-6 alkylene) glycol, a polyethylene glycol, C1-3 alkyl-(OCH2CH2)1-5-OH, DMSO, ethyl acetate, acetone, N-methyl pyrrolidone, benzyl alcohol, glycerin, and an oil; the gelling agent is hydroxypropyl cellulose having a molecular weight ranging from about 40,000 Dato about 2,500,000 Da; and wherein the gelled topical formulation has a viscosity of from 1 to 25,000 cps; and DMSO, when present, is combined with at least one other of said organic solvents such that DMSO is present in an amount of less than 50% by weight.

  本文提供了用于治疗皮肤疾病的凝胶局部制剂，包括：a) MEK抑制剂；b) 一种或多种有机溶剂，其重量约为70%至99%；和c) 凝胶剂；其中所述一种或多种有机溶剂选自以下组：C2-6醇，C2-6烷基二醇，二-(C2-6烷基)二醇，聚乙二醇，C1-3烷基-(OCH2CH2)1-5-OH，二甲基亚砜，乙酸乙酯，丙酮，N-甲基吡咯烷酮，苯甲醇，甘油和一种油；所述凝胶剂为分子量范围约为40,000 Da至2,500,000 Da的羟丙基纤维素；其中所述凝胶局部制剂的粘度为1至25,000 cps；当存在DMSO时，将DMSO与至少一种其他所述有机溶剂结合，使DMSO的重量不超过50%。
• Heterocyclic inhibitors of MEK and methods of use thereof
  申请人：Wallace Eli

  公开号：US20050049419A1

  公开（公告）日：2005-03-03

  Disclosed are compounds of the Formula I and pharmaceutically acceptable salts and prodrugs thereof, wherein R 1 , R 2 , R 7 , R 8 , R 9 and R 10 , W and Y are as defined in the specification. Such compounds are MEK inhibitors and useful in the treatment of hyperproliferative diseases, such as cancer and inflammation, in mammals. Also disclosed are methods of using such compounds in the treatment of hyperproliferative diseases in mammals and pharmaceutical compositions containing such compounds.

  本发明涉及具有式I的化合物及其药用可接受的盐和前药，其中R1、R2、R7、R8、R9和R10、W和Y如规范中所定义。这些化合物是MEK抑制剂，在哺乳动物中用于治疗高增殖性疾病，如癌症和炎症。还公开了在哺乳动物中使用这些化合物治疗高增殖性疾病的方法以及含有这些化合物的药物组合物。
• N3 alkylated benzimidazole derivatives as MEK inhibitors
  申请人：——

  公开号：US20040116710A1

  公开（公告）日：2004-06-17

  Disclosed are compounds of the formula I 1 and pharmaceutically acceptable salts and prodrugs thereof, wherein W, R 1 , R 2 , R 7 , R 8 , R 9 and R 10 are as defined in the specification. Such compounds are MEK inhibitors and useful in the treatment of hyperproliferative diseases, such as cancer and inflammation, in mammals. Also disclosed is a method of using such compounds in the treatment of hyperproliferative diseases in mammals, and pharmaceutical compositions containing such compounds.

  公开了公式I1的化合物以及药用可接受的盐和前药，其中W，R1，R2，R7，R8，R9和R10如说明书所定义。这类化合物是MEK抑制剂，可用于治疗哺乳动物中的过度增殖性疾病，如癌症和炎症。还公开了一种使用这些化合物治疗哺乳动物中过度增殖性疾病的方法，以及含有这些化合物的药物组合物。
• [EN] NOVEL 6-ARYLAMINO PYRIDONE CARBOXAMIDE AS MEK INHIBITORS<br/>[FR] NOUVEAUX 6-ARYLAMINOPYRIDONECARBOXAMIDES COMME INHIBITEURS DE MEK
  申请人：CENTAURUS BIOPHARMA CO LTD

  公开号：WO2012059041A1

  公开（公告）日：2012-05-10

  The invention provides novel substituted 6-arylamino pyridone carboxamides represented by Formula I, or a pharmaceutically acceptable salt, solvate, poly- morph, ester, tautomer or prodrug thereof, and a composition comprising these compounds. The compounds provided can be used as inhibitors of MEK and are useful in the treatment of inflammatory diseases, cancer and other hyperproliferative diseases. The invention further provides a method of treatment for inflammatory diseases, cancer and other hyperproliferative diseases in mammals, especially humans.

  该发明提供了由式I表示的新型取代6-芳基氨基吡啶酮甲酰胺，或其药学上可接受的盐、溶剂化合物、多形体、酯、互变异构体或前药，以及包含这些化合物的组合物。所提供的化合物可用作MEK的抑制剂，并且在治疗炎症性疾病、癌症和其他过度增殖性疾病方面具有用途。该发明还提供了一种治疗哺乳动物，特别是人类的炎症性疾病、癌症和其他过度增殖性疾病的方法。