5-乙酰基-2,3-二氢苯并[b]呋喃 | 90843-31-5

• 物质功能分类: 医药中间体 - 原料药中间体
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 5-乙酰基-2,3-二氢苯并[b]呋喃
• 中文别名: 1-(2,3-二氢苯并[b]呋喃-5-基)-1-乙酮；5-乙酰基-2,3-二氢苯并[B]呋喃；5-乙酰基-2,3-二氢苯并呋喃；1-(2,3-二氢苯并[B]呋喃-5-基)-1-乙酮；1-(2,3-二氢苯并呋喃-5-基)乙酮
• 英文名称: 1-(2,3-dihydrobenzofuran-5-yl)ethanone
• 英文别名: 5-acetyl-2,3-dihydrobenzofuran；1-(2,3-dihydrobenzofuran-5-yl)ethan-1-one；5-Acetyl-2,3-dihydrobenzo[b]furan；1-(2,3-dihydro-1-benzofuran-5-yl)ethanone
• CAS: 90843-31-5
• 化学式: C₁₀H₁₀O₂
• mdl: MFCD00068033
• 分子量: 162.188
• InChiKey: MMVUJVASBDVNGJ-UHFFFAOYSA-N

物化性质

• 熔点：
  56-59°C
• 沸点：
  120-121°C 15mm
• 密度：
  1.149±0.06 g/cm3(Predicted)
• 闪点：
  120-121°C/15mm
• 稳定性/保质期：

  按规定使用和贮存的情况下，该物质不会分解，并能避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xn
• WGK Germany：
  3
• RTECS号：
  MU2800000
• 海关编码：
  2932999099
• 危险类别：
  6.1(b)
• 安全说明：
  S22,S36/37,S45
• 危险类别码：
  R22,R42/43
• 包装等级：
  III
• 危险品运输编号：
  2811
• 危险性防范说明：
  P261,P301+P312,P302+P352,P304+P340,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存放于密闭、阴凉且干燥的地方。

SDS

Name:	1-(2 3-Dihydrobenzo[b]furan-5-yl)ethan-1-one 97% Material Safety Data Sheet
Synonym:	5-Acetyl-2,3-dihydrobenzo[b]fura
CAS:	90843-31-5

Section 1 - Chemical Product MSDS Name:1-(2 3-Dihydrobenzo[b]furan-5-yl)ethan-1-one 97% Material Safety Data Sheet
Synonym:5-Acetyl-2,3-dihydrobenzo[b]fura

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
90843-31-5	1-(2,3-Dihydrobenzo[b]furan-5-yl)ethan	97%	unlisted

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

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

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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.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately.
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.
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.

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Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
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:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 90843-31-5: Personal Protective Equipment Eyes: Not available.
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: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 56 - 59 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: C10H10O2
Molecular Weight: 162

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 90843-31-5 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
1-(2,3-Dihydrobenzo[b]furan-5-yl)ethan-1-one - 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
No information available.
IMO
No information available.
RID/ADR
No information available.

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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# 90843-31-5: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 90843-31-5 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 90843-31-5 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

制备方法与用途

5-乙酰基-2,3-二氢苯并呋喃是一种白色粉末状结晶，是合成抗炎镇痛药2,3-二氢苯并呋喃-2-羧酸类的有机中间体。

该化合物可通过以下步骤制备：以邻溴苯酚为原料，在水作溶剂的情况下，与1,2-二氯乙烷、氢氧化钠和亚硫酸氢钠在苄基三丁基氯化铵（一种相转移催化剂）的作用下进行加热回流反应，发生烷基化反应。随后，该产物在无水四氢呋喃中与1,2-二溴乙烷及镁反应即可获得目标化合物2,3-二氢苯并呋喃。此方法步骤简洁、时间较短，后续处理简单，收率高达76.6%，具有良好的应用前景。

反应路线如下：

反应信息

• 作为反应物：
  描述：

  5-乙酰基-2,3-二氢苯并[b]呋喃 在 sodium tetrahydroborate 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 24.0h， 生成 达非那新
  参考文献：
  名称：

  A New Solvent System (Cyclopentyl Methyl Ether–Water) in Process Development of Darifenacin HBr

  摘要：

  Darifenacin is a potent and competitive M-3 selective receptor antagonist (M(3)SRA), and its hydrobromide salt (1) is the active ingredient of pharmaceutical formulations for oral treatment of urinary incontinence. The present work demonstrates an efficient, commercial manufacturing process for darifenacin hydrobromide (1).

  DOI：

  10.1021/op300119s
• 作为产物：
  描述：

  2,3-二氢苯并呋喃 在 aluminum (III) chloride 、 盐酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.75h， 以94%的产率得到5-乙酰基-2,3-二氢苯并[b]呋喃
  参考文献：
  名称：

  WO2006/104406

  摘要：

  公开号：
• 作为试剂：
  描述：

  乙酰氯 、 三氯化铝 、 4-(1H-4-吲哚)-哌嗪-1-羧酸叔丁酯 、 2,3-二氢苯并呋喃 、 在 二氯甲烷 、 Sodium sulfate-III 、 乙酸乙酯 、 5-乙酰基-2,3-二氢苯并[b]呋喃 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以This resulted in 67 g (94%) of 1-(2,3-dihydrobenzofuran-5-yl)ethanone as a yellow solid的产率得到5-乙酰基-2,3-二氢苯并[b]呋喃
  参考文献：
  名称：

  4' SUBSTITUTED COMPOUNDS HAVING 5-HT6 RECEPTOR AFFINITY

  摘要：

  本公开提供了具有亲和力的5-HT6受体的化合物，其化学式为(I)：其中R1、R2、R5、R6、B、D、E、G、Q、x和n如本文所定义。该公开还涉及制备这种化合物的方法、含有这种化合物的组合物以及使用这种化合物的方法。

  公开号：

  US20080318941A1

文献信息

• Azabicyclic compounds for the treatment of disease
  申请人：——

  公开号：US20030232853A1

  公开（公告）日：2003-12-18

  The invention provides compounds of Formula I: 1 wherein Azabicyclo is 2 These compounds may be in the form of pharmaceutical salts or compositions, may be in pure enantiomeric form or racemic mixtures, and are useful in pharmaceuticals in which &agr;7 is known to be involved.

  这项发明提供了Formula I的化合物： 其中Azabicyclo是 这些化合物可以是药用盐或组合物的形式，可以是纯对映体形式或混合物，对已知涉及α7的药物具有用处。
• [EN] PROCESS FOR THE SYNTHESIS OF RAMELTEON AND ITS INTERMEDIATES<br/>[FR] PROCÉDÉ DE SYNTHÈSE DU RAMELTEON ET DE SES INTERMÉDIAIRES
  申请人：TEVA PHARMA

  公开号：WO2010045565A1

  公开（公告）日：2010-04-22

  The present invention provides processes and intermediates for the synthesis of ramelteon.

  本发明提供了拉莫特普合成的工艺和中间体。
• Synthesis of Chiral α-Amino Tertiary Boronic Esters by Enantioselective Hydroboration of α-Arylenamides
  作者：Naifu Hu、Guoqing Zhao、Yuanyuan Zhang、Xiangqian Liu、Guangyu Li、Wenjun Tang

  DOI：10.1021/jacs.5b03760

  日期：2015.6.3

  rhodium-catalyzed asymmetric hydroboration of α-arylenamides with BI-DIME as the chiral ligand and (Bpin)2 as the reagent yields for the first time a series of α-amino tertiary boronic esters in good yields and excellent enantioselectivities (up to 99% ee).

  以 BI-DIME 作为手性配体和 (Bpin)2 作为试剂的 α-芳基酰胺的铑催化不对称硼氢化反应首次以良好的收率和优异的对映选择性（高达 99 % ee）。
• α‐Functionalisation of Ketones Through Metal‐Free Electrophilic Activation
  作者：Wojciech Zawodny、Christopher J. Teskey、Magdalena Mishevska、Martin Völkl、Boris Maryasin、Leticia González、Nuno Maulide

  DOI：10.1002/anie.202006398

  日期：2020.11.16

  electrophilic intermediates that can undergo a variety of transformations when treated with nucleophiles. This electrophilic ketone activation gives access to α‐arylated and α‐oxyaminated acetophenones under metal‐free conditions in moderate to excellent yields and enables extension to the synthesis of arylated morpholines via generation of vinylsulfonium salts. Computational investigations confirmed the transient

  三氟甲磺酸酐介导的苯乙酮活化会产生高度亲电的中间体，当用亲核试剂处理时，该中间体会发生多种转变。这种亲电子酮活化可以在无金属条件下以中等至优异的产率获得 α-芳基化和 α-氧基胺化苯乙酮，并能够通过生成乙烯基锍盐扩展到芳基化吗啉的合成。计算研究证实了衍生自三氟甲磺酸乙烯酯的中间体的短暂存在以及芳环对位的氧原子在促进其稳定方面的作用。
• Substituted 4-oxo-crotonic acid derivatives as a new class of protein kinase B (PknB) inhibitors: synthesis and SAR study
  作者：Changliang Xu、Xiaoguang Bai、Jian Xu、Jinfeng Ren、Yun Xing、Ziqiang Li、Juxian Wang、Jingjing Shi、Liyan Yu、Yucheng Wang

  DOI：10.1039/c6ra24953a

  日期：——

  Protein kinase B (PknB) is an essential serine/threonine protein kinase required for Mycobacterium tuberculosis (M. tb) cell division and cell-wall biosynthesis. A high throughput screen using PknB identified a (E)-4-oxo-crotonic acid inhibitor, named YH-8, which was used as a scaffold for SAR investigations. A significant improvement in enzyme affinity was achieved. The results indicated that the

  蛋白激酶B（PknB）是结核分枝杆菌（M. tb）细胞分裂和细胞壁生物合成所必需的丝氨酸/苏氨酸蛋白激酶。使用PknB进行的高通量筛选鉴定出一种名为YH-8的（E）-4-氧代巴豆酸抑制剂，该抑制剂被用作SAR研究的支架。实现了酶亲和力的显着改善。结果表明，α，β-不饱和酮骨架和“反式”构型对于对抗PknB的活性至关重要。而且具有芳基的化合物，特别是在苯环上具有吸电子取代基的化合物，其效能是YH-8的四倍。