2,3-二氢-5-硝基-苯并呋喃 | 17403-47-3

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 中文名称: 2,3-二氢-5-硝基-苯并呋喃
• 中文别名: 5-硝基-2,3-二氢苯并呋喃
• 英文名称: 5-nitro-2,3-dihydrobenzofuran
• 英文别名: 5-Nitro-2,3-dihydro-1-benzofuran
• CAS: 17403-47-3
• 化学式: C₈H₇NO₃
• 分子量: 165.148
• InChiKey: TYPKKUFDAHEIOP-UHFFFAOYSA-N

物化性质

• 沸点：
  292.3±29.0 °C(Predicted)
• 密度：
  1.360±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2932999099
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  2-8°C，干燥密封

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 5-Nitro-2,3-dihydro-1-benzofuran
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: 5-Nitro-2,3-dihydro-1-benzofuran
CAS number: 17403-47-3

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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: C8H7NO3
Molecular weight: 165.1

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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：

  2,3-二氢-5-硝基-苯并呋喃 在 tin(II) chloride dihdyrate 、 水 、 碳酸氢钠 作用下， 以 乙醇 为溶剂， 反应 5.5h， 以65%的产率得到5-氨基-2,3-二氢苯并[b]呋喃
  参考文献：
  名称：

  N 3-苯基吡嗪并酮作为促肾上腺皮质激素释放因子-1（CRF 1）受体拮抗剂的基于内在清除的优化。

  摘要：

  一系列基于吡嗪酮的杂环被鉴定为有效的和口服活性的促肾上腺皮质激素释放因子1（CRF 1）受体拮抗剂。所选择的化合物在大鼠焦虑模型中证明是有效的。但是，药代动力学特性不是最佳的。在本文中，我们描述了一种基于体外固有清除率的方法，用于优化基于吡嗪酮的CRF 1受体拮抗剂，其中通过与人肝微粒体孵育来确定代谢位点。发现通过在代谢的主要位点掺入适当的取代基可以降低代谢速率。这导致发现化合物12x，高效能（IC 50 = 1.0 nM）和选择性CRF1种受体拮抗剂，在大鼠中具有良好的口服生物利用度（F = 52％），并且在大鼠的防御性戒断焦虑测试中具有疗效。

  DOI：

  10.1021/jm900302q
• 作为产物：
  描述：

  2,3-二氢苯并呋喃 在 硝酸 、 溶剂黄146 作用下， 反应 2.0h， 以17%的产率得到2,3-二氢-5-硝基-苯并呋喃
  参考文献：
  名称：

  设计，结构-活性关系和作为新型神经激肽-1受体拮抗剂的3-苯基-4-苄基氨基哌啶衍生物的高效不对称合成

  摘要：

  我们合成了一系列新颖的3-苯基-4-苄基氨基哌啶衍生物，这些衍生物通过通过高通量筛选对3-苯甲酰基哌啶酮衍生物进行结构修饰而被鉴定为有效的速激肽NK 1受体拮抗剂。N- {2-[（3 R，4 S）-4-（{2-甲氧基-5- [5-（三氟甲基）-1] H-四唑-1-基]苄基}氨基）-3-苯基-1 -哌啶基] -2-氧代乙基}乙酰胺（（+）- 39）被发现是最有效的速激肽NK 1受体拮抗剂，具有高代谢稳定性。通过动态动力学拆分实现了（+）- 39的高效不对称合成。

  DOI：

  10.1016/j.bmc.2011.08.070

文献信息

• Cyclic (Alkyl)(amino)carbene Ligand-Promoted Nitro Deoxygenative Hydroboration with Chromium Catalysis: Scope, Mechanism, and Applications
  作者：Lixing Zhao、Chenyang Hu、Xuefeng Cong、Gongda Deng、Liu Leo Liu、Meiming Luo、Xiaoming Zeng

  DOI：10.1021/jacs.0c12318

  日期：2021.1.27

  Transition metal catalysis that utilizes N-heterocyclic carbenes as noninnocent ligands in promoting transformations has not been well studied. We report here a cyclic (alkyl)(amino)carbene (CAAC) ligand-promoted nitro deoxygenative hydroboration with cost-effective chromium catalysis. Using 1 mol % of CAAC-Cr precatalyst, the addition of HBpin to nitro scaffolds leads to deoxygenation, allowing for

  利用 N-杂环卡宾作为非无害配体促进转化的过渡金属催化尚未得到很好的研究。我们在这里报告了具有成本效益的铬催化的环状（烷基）（氨基）卡宾（CAAC）配体促进的硝基脱氧硼氢化反应。使用 1 mol % 的 CAAC-Cr 预催化剂，将 HBpin 添加到硝基支架上会导致脱氧，从而保留各种可还原的官能团和敏感基团对硼氢化的相容性，从而提供一种温和、化学选择性和易于形成的策略苯胺，以及杂芳基和脂肪胺衍生物，具有广泛的范围和特别高的转换数（高达 1.8 × 106）。基于理论计算的机械研究，表明CAAC配体在促进HBpin氢化物极性反转中起重要作用；它用作 H 穿梭以促进脱氧硼氢化。通过这种策略制备的几种市售药物突出了其在药物化学中的潜在应用。
• Chromium-Catalyzed Activation of Acyl C–O Bonds with Magnesium for Amidation of Esters with Nitroarenes
  作者：Liang Ling、Changpeng Chen、Meiming Luo、Xiaoming Zeng

  DOI：10.1021/acs.orglett.9b00554

  日期：2019.3.15

  chromium-catalyzed activation of acyl C–O bonds with magnesium for amidation of esters with nitroarenes. Low-cost chromium(III) chloride shows high reactivity in promoting amidation by using magnesium as reductant and chlorotrimethylsilane as additive. It provides a step-economic strategy to the synthesis of centrally important amide motifs using inexpensive and air-stable nitroarenes as amino sources.

  在这里，我们报道了铬与镁催化的羰基C–O键活化，从而使酯与硝基芳烃酰胺化。通过使用镁作为还原剂和氯代三甲基硅烷作为添加剂，低成本的氯化铬（III）在促进酰胺化方面显示出高反应活性。它为使用廉价且空气稳定的硝基芳烃作为氨基源合成重要的酰胺基序提供了分步经济策略。
• [EN] GLUCOCORTICOID MIMETICS, METHODS OF MAKING THEM, PHARMACEUTICAL COMPOSITIONS, AND USES THEREOF<br/>[FR] MIMETIQUES DU GLUCOCORTICOIDE, PROCEDES DE FABRICATION DE CES MIMETIQUES, COMPOSITIONS PHARMACEUTIQUES ET LEURS UTILISATIONS
  申请人：BOEHRINGER INGELHEIM PHARMA

  公开号：WO2003082787A1

  公开（公告）日：2003-10-09

  Compounds of Formula (IA) and Formula (IB) wherein R1, R2, R3, R4, R5, and R6 are as defined herein for Formula (IA) or Formula (IB), or a tautomer, prodrug, solvate,or salt thereof; pharmaceutical compositions containing such compounds, and methods of modulating the glucocorticoid receptor function and methods of treating disease-states or conditions mediated by the glucocorticoid receptor function or characterized by inflammatory, allergic, or proliferative processes in a patient using these compounds.

  式（IA）和式（IB）的化合物，其中R1、R2、R3、R4、R5和R6如本说明所定义的适用于式（IA）或式（IB），或其互变异构体、前药、溶剂化合物或盐；含有这些化合物的药物组合物，以及利用这些化合物调节糖皮质激素受体功能的方法、治疗由糖皮质激素受体功能介导的疾病状态或病情特征或患者体内的炎症、过敏或增殖过程的方法。
• Deoxygenation of Nitrous Oxide and Nitro Compounds Using Bis(N‐Heterocyclic Silylene)Amido Iron Complexes as Catalysts
  作者：Xi Chen、Hao Wang、Shaozhi Du、Matthias Driess、Zhenbo Mo

  DOI：10.1002/anie.202114598

  日期：2022.2.7

  The efficient catalytic degradation of N2O to N2 by well-defined bis(silylene)amido iron complexes under mild conditions involving the cooperative effect between the iron and silylene ligands is reported. Selective reductions of nitro compounds to amino-boranes with good functional-group tolerance and excellent chemo-selectivity have been developed using the same approach.

  报道了在温和条件下通过明确的双（亚硅基）氨基铁络合物将 N 2 O高效催化降解为 N 2 ，这涉及铁和亚硅基配体之间的协同作用。已经使用相同的方法开发了将硝基化合物选择性还原为具有良好官能团耐受性和优异化学选择性的氨基硼烷。
• Tricyclic furo-quinazolinones
  申请人：Sandoz, Inc.

  公开号：US03963717A1

  公开（公告）日：1976-06-15

  Anti-inflammatories and analgesics of the formula ##SPC1## Wherein X y is --OCH.sub.2 CH.sub.2 -- or --CH.sub.2 CH.sub.2 O--, R is lower alkyl, allyl or cycloalkylalkyl and R' is phenyl or phenyl monosubstituted by halo, alkyl, alkoxy or trifluoromethyl, Are prepared by oxidation of the corresponding dihydro intermediates.

  该公式的抗炎药和止痛药为##SPC1##，其中X y为--OCH.sub.2 CH.sub.2--或--CH.sub.2 CH.sub.2 O--，R为低碳烷基、烯丙基或环烷基烷基，R'为苯基或被卤素、烷基、烷氧基或三氟甲基单取代的苯基，通过氧化相应的二氢中间体制备。