2-甲氧基乙基异氰化物 | 43219-50-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 2-甲氧基乙基异氰化物
• 英文名称: 2-methoxyethyl isocyanide
• 英文别名: 1-Isocyano-2-methoxyethane
• CAS: 43219-50-7
• 化学式: C₄H₇NO
• mdl: MFCD06200529
• 分子量: 85.1057
• InChiKey: RXRQOZYTUCHGHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  6
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  13.6
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2926909090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1-Isocyano-2-methoxyethane
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: 1-Isocyano-2-methoxyethane
CAS number: 43219-50-7

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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, refrigerated.
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: C4H7NO
Molecular weight: 85.1

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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

反应信息

• 作为反应物：
  描述：

  2-甲氧基乙基异氰化物 、 2-氨基二苯甲酮 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到3-(2-Methoxyethyl)-4-phenylquinazolin-4-ol
  参考文献：
  名称：

  BF3·OEt2-promoted reaction of isocyanides with o-aminobenzophenones

  摘要：

  Aliphatic isocyanides react with o-aminobenzophenones in dichloromethane under Lewis acid catalysis at ambient temperature to give, unexpectedly, 4-aryl-4-hydroxy-3,4-dihydroquinazolines in good to excellent yields. The outcome of the reaction is rationalized by a skeletal rearrangement of the initially formed 'intramolecular Passerini' reaction products, 2-amino-3-hydroxy-3-aryl-3H-indoles. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.08.031
• 作为产物：
  描述：

  N-甲酰基-O-甲基乙醇胺 在 三乙胺 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 生成 2-甲氧基乙基异氰化物
  参考文献：
  名称：

  Preparation and biodistribution of novel99mTc(CO)3-CNR complexes for myocardial imaging

  摘要：

  我们评估了一系列99mTc(CO)3-乙醚异腈复合物的亲脂性和生物分布，以确定异腈配体的不同亲脂性和结构是否能够改善心脏放射性药物的成像特性。我们制备了新型99mTc(CO)3-MIBI类似物，并通过放射-HPLC对其进行了分析，确定了它们的亲脂性。这些新复合物在特定的pH条件下可以像99mTc(CO)3-MIBI一样进行双取代或三取代。与[99mTc(CO)3(MIBI)3]+相比，这些新复合物在肝脏、肺部和血液中的摄取量较低，但心脏摄取量并不高。在这些复合物中，[99mTc(CO)3(EPI)2(OH2)]+在注射后5分钟和30分钟的目标与非目标比率高于[99mTc(CO)3(MIBI)3]+。版权所有 © 2007 John Wiley & Sons, Ltd.

  DOI：

  10.1002/jlcr.1151

文献信息

• Exploitation of the Ugi–Joullié Reaction in the Synthesis of Libraries of Drug-Like Bicyclic Hydantoins
  作者：Adam Nelson、James Firth、Rong Zhang、Rémy Morgentin、Rachel Guilleux、Tuomo Kalliokoski、Stuart Warriner、Richard Foster、Stephen Marsden

  DOI：10.1055/s-0034-1378704

  日期：——

  efficient method for the synthesis of drug-like fused bicyclic hydantoins is reported. An Ugi–Joullié reaction/cyclisation sequence was exploited as the key complexity-generating process in which trifluoroacetic acid was employed as synthetic equivalent for chloroformic acid. Exemplar diversification of the bicyclic scaffolds was performed to enable subsequent translation to the synthesis of large small molecule

  摘要 报道了合成药物样稠合双环乙内酰脲的通用且有效的方法。Ugi-Joullié反应/环化序列被用作关键的复杂性生成过程，在该过程中，三氟乙酸被用作氯甲酸的合成等价物。进行了双环支架的典型多样化，以使其能够随后翻译为大分子小分子文库的合成，从而导致生产了> 1000种化合物，从而增加了欧洲铅厂的筛选。 报道了合成药物样稠合双环乙内酰脲的通用且有效的方法。Ugi-Joullié反应/环化序列被用作关键的复杂性生成过程，在该过程中，三氟乙酸被用作氯甲酸的合成等价物。进行了双环支架的典型多样化，以使其能够随后翻译为大分子小分子文库的合成，从而导致生产了> 1000种化合物，从而增加了欧洲铅厂的筛选。
• Palladium and copper catalyzed cyclizations of hydrazine derived Ugi products: facile synthesis of substituted indazolones and hydroxytriazafluorendiones
  作者：Sebastian J. Welsch、Cédric Kalinski、Michael Umkehrer、Günther Ross、Jürgen Kolb、Christoph Burdack、Ludger A. Wessjohann

  DOI：10.1016/j.tetlet.2012.02.095

  日期：2012.5

  Indazolones are medicinally relevant targets. Herein we disclose an improved synthesis to N′-(acetamido-2-yl)-substituted indazolones with four points of diversity introduced by Ugi-[M]-amination and -amidation. The ring closure can be achieved by either conventional palladium catalysis or with a ligandless copper protocol. When α-unbranched isocyanides were employed the sole cyclization products of

  吲唑酮是医学上相关的靶标。在本文中，我们公开了通过Ugi- [M]-氨基化和-酰胺化引入的具有四个多样性点的N '-（乙酰氨基-2-基）-取代的吲唑酮的合成方法。闭环可以通过常规的钯催化或无配体的铜方案来实现。当使用α-非支化异氰酸酯时，铜催化反应的唯一环化产物是迄今未描述的2-羟基-3 H -3,4a，9a-三氮杂芴-4,9-二酮。
• Synthesis of substituted imidazolines by an Ugi/Staudinger/aza-Wittig sequence
  作者：Sebastian J. Welsch、Michael Umkehrer、Cedric Kalinski、Günther Ross、Christoph Burdack、Jürgen Kolb、Martina Wild、Anja Ehrlich、Ludger A. Wessjohann

  DOI：10.1016/j.tetlet.2015.01.043

  日期：2015.2

  A series of 2-(acetamide-2-yl)-imidazolines (II) with 5 points of diversity were prepared by an Ugi-4CR–Staudinger–aza-Wittig-sequence starting from simple azidoalkylamines. The intramolecular aza-Wittig cyclization between the iminophosphane and the tertiary amide of the Ugi product (I) was effected by short microwave irradiation. Competitive cyclization to the secondary amide was not relevant, however

  由Ugi-4CR–Staudinger–aza-Wittig-序列从简单的叠氮基烷基胺开始制备了具有5个多样性点的一系列2-（乙酰胺-2-基）-咪唑啉（II）。Ugi产品（I）的亚氨基膦与叔酰胺之间的分子内氮杂-维蒂希环化反应是通过短波微波辐射进行的。与仲酰胺的竞争性环化无关紧要，但是，在某些情况下，观察到随后形成了双环邻位am（III）。
• PdII/IV catalyzed oxidative cyclization of 1,6-enynes derived by Ugi-4-component reaction
  作者：Sebastian J. Welsch、Michael Umkehrer、Günther Ross、Jürgen Kolb、Christoph Burdack、Ludger A. Wessjohann

  DOI：10.1016/j.tetlet.2011.09.094

  日期：2011.11

  A variety of 1,6-enynes were synthesized by an Ugi-reaction and further elaborated by a PdII/IV catalyzed oxidative cyclization to produce N-substituted 3-aza-bicyclo[3.1.0]hexan-2-ones. Different substitution patterns were tested to examine the scope and limitations of the amide tethered substrates.

  通过Ugi反应合成了各种1，6-烯炔，并通过Pd II / IV催化的氧化环化反应进一步精制，以产生N-取代的3-氮杂-双氮杂双环[3.1.0]己-2-烯。测试了不同的取代模式以检查酰胺束缚底物的范围和局限性。
• Construction of a Shape‐Diverse Fragment Set: Design, Synthesis and Screen against Aurora‐A Kinase
  作者：Rong Zhang、Patrick J. McIntyre、Patrick M. Collins、Daniel J. Foley、Christopher Arter、Frank von Delft、Richard Bayliss、Stuart Warriner、Adam Nelson

  DOI：10.1002/chem.201900815

  日期：2019.5.10

  resulting set of 80 fragments was highly three‐dimensional, and its shape diversity was significantly enriched by twenty synthesised fragments. The fragment set was screened by high‐throughput protein crystallography against Aurora‐A kinase, revealing four hits that targeted the binding site of allosteric regulators. In the longer term, it is envisaged that the fragment set could be screened against a range

  从历史上看，化学家们以高度不平衡和不系统的方式探索化学空间。例如，现有片段集的形状多样性通常不会反映所有理论上可能的片段的形状多样性。为了通过实验评估增加的三维度的附加值，设计并整理了形状多样的片段集。使用市售片段并利用统一的合成方法对sp 3进行组装富含分子的支架。所得的80个片段集是高度三维的，其形状多样性被20个合成片段显着丰富。通过针对Aurora-A激酶的高通量蛋白质晶体学筛选了该片段集，揭示了四个靶向变构调节因子结合位点的命中。从长远来看，可以针对一系列功能多样的蛋白质筛选片段集，从而可以更全面地评估更多形状多样的筛选集合的附加值。