4-溴-3,6-二氢-2H-吡喃 | 24265-23-4

• 物质功能分类: 医药中间体 - 吡喃类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 中文名称: 4-溴-3,6-二氢-2H-吡喃
• 英文名称: 4-bromo-3,6-dihydro-2H-pyran
• CAS: 24265-23-4
• 化学式: C₅H₇BrO
• 分子量: 163.014
• InChiKey: WSVCDRYCXKRMRC-UHFFFAOYSA-N

物化性质

• 沸点：
  184.5±40.0 °C(Predicted)
• 密度：
  1.580±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2932999099

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: 4-Bromo-3,6-dihydro-2H-pyran
Synonyms:

---

Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.

---

Section 3. Composition/information on ingredients.
Ingredient name: 4-Bromo-3,6-dihydro-2H-pyran
CAS number: 24265-23-4

---

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.

---

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.

---

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.

---

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, under −20◦C.
Storage:

---

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.

---

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: C5H7BrO
Molecular weight: 163.0

---

Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, hydrogen bromide.

---

Section 11. Toxicological information
No data.

---

Section 12. Ecological information
No data.

---

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.

---

Section 14. Transportation information
Non-harzardous for air and ground transportation.

---

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.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

化学性质 4-溴-3,6-二氢-2H-吡喃是一种含有六元环的有机化合物，在4号位有一个溴原子取代，并且3号和6号位的碳原子各有一个氢原子，使这些位置的碳原子处于饱和状态。这种结构通常赋予该化合物较好的有机溶剂溶解性，由于溴原子的存在，它可能在化学反应中表现出一定的活性，例如参与取代或消除反应。

外观 4-溴-3,6-二氢-2H-吡喃为淡黄色油状液体。

用途 4-溴-3,6-二氢-2H-吡喃是一种用于有机合成及科研实验的吡喃类衍生物。

合成方法 将四氢吡喃-4-酮（10.0克，0.1摩尔）、对甲基甲苯（18.6克，0.1摩尔）和乙醇120 mL混合后，加热回流反应。反应完成后蒸发掉溶剂，直接加入DBU（22.8g，0.15摩尔）和150毫升二氯甲烷中，然后滴加NBS（26.7克，0.15mol）溶解在40 mL二氯甲烷溶液中。反应完成后，通过加入10%盐酸调节pH至4-5，分离有机层，在常压下蒸发溶剂，再通过加入20 mL环丁砜进行真空蒸馏，最终获得12.2 g浅黄色液体：4-溴-3,6-二氢-2H-吡喃。气相色谱分析显示纯度为98.4%，产率为75%。

反应信息

• 作为反应物：
  描述：

  4-溴-3,6-二氢-2H-吡喃 在 tris-(dibenzylideneacetone)dipalladium(0) 、 copper(l) iodide 、 caesium carbonate 、 N,N-二甲基乙二胺 、 2-二环己膦基-2'-(N,N-二甲胺)-联苯 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 生成 1-(3,6-dihydro-2H-pyran-4-yl)-3-[6-[(2,4-dimethoxyphenyl)methylamino]pyridin-3-yl]-3,5,5-trimethylpyrrolidin-2-one
  参考文献：
  名称：

  TYK2 INHIBITORS AND USES THEREOF

  摘要：

  本发明提供了化合物、其组合物以及使用这些化合物来抑制TYK2并治疗TYK2介导的疾病的方法。

  公开号：

  US20160251376A1
• 作为产物：
  描述：

  3,6-二氢-2H-吡喃-4-三氟甲烷磺酸盐 在 bis(1,5-cyclooctadiene)nickel (0) 、 lithium bromide 作用下， 以 四氢呋喃 、 N,N-二甲基乙酰胺 为溶剂， 以64%的产率得到4-溴-3,6-二氢-2H-吡喃
  参考文献：
  名称：

  镍催化烯醇三氟甲磺酸酯转化为烯基卤化物。

  摘要：

  开发了镍催化的烯醇三氟甲磺酸酯卤化反应，能够在温和的反应条件下合成多种烯基碘化物、溴化物和氯化物。该反应使用廉价、实验室稳定的 Ni(OAc)2·4 H2 O 作为预催化剂，并在亚化学计量的 Zn 和 1,5-环辛二烯或 4-(N,N-二甲基氨基) 存在下在室温下进行吡啶。

  DOI：

  10.1002/anie.201906815

文献信息

• HETEROCYCLICALLY SUBSTITUTED ARYL COMPOUNDS AS HIF INHIBITORS
  申请人：Härter Michael

  公开号：US20130196964A1

  公开（公告）日：2013-08-01

  The present application relates to novel aryl compounds with heterocyclic substituents, processes for their preparation, their use for treatment and/or prevention of diseases and their use for the preparation of medicaments for treatment and/or prevention of diseases, in particular for treatment and/or prevention of hyperproliferative and angiogenic diseases and those diseases which arise from metabolic adaptation to hypoxic states. Such treatments can be carried out as monotherapy or also in combination with other medicaments or further therapeutic measures.

  本申请涉及具有杂环取代基的新型芳基化合物，其制备方法，它们用于治疗和/或预防疾病以及用于制备治疗和/或预防疾病的药物，特别是用于治疗和/或预防过度增殖和血管生成性疾病以及那些由于代谢适应缺氧状态而引起的疾病。这种治疗可以作为单独治疗进行，也可以与其他药物或进一步治疗措施结合使用。
• Rhodium-Catalyzed Enantioselective Intramolecular Hydroacylation of Trisubstituted Alkenes
  作者：Kirsten F. Johnson、Eugene A. Schneider、Brian P. Schumacher、Arkady Ellern、Joseph D. Scanlon、Levi M. Stanley

  DOI：10.1002/chem.201603880

  日期：2016.10.24

  We report the first examples of transition metal‐catalyzed enantioselective alkene hydroacylations with 1,1,2‐trisubstituted alkenes. DFT and mechanistic studies are consistent with a reaction pathway for these rhodium‐catalyzed processes including intramolecular alkene hydroacylation and α‐epimerization to generate highly enantioenriched, polycyclic architectures. This reaction sequence enables the

  我们报告了第一个用1,1,2-三取代烯烃进行过渡金属催化的对映选择性烯烃加氢酰化的例子。DFT和机理研究与这些铑催化过程的反应途径一致，这些过程包括分子内烯烃加氢酰化和α-表异构化以生成高度对映体富集的多环结构。该反应顺序使2-（环己-1-烯-1-基）苯甲醛的加氢酰化，以形成六氢-9- ħ芴-9-酮在中度到高的产率（68-91％）与高对映选择性（高达99％ee）和非对映选择性（通常> 20：1）。
• 含杂原子环己烯卤代物的制备方法
  申请人：蚌埠产品质量监督检验研究院

  公开号：CN110563696B

  公开（公告）日：2022-05-03

  本发明公开了含杂原子环己烯卤代物的制备方法，属于精细化工中间体合成领域。以含杂原子环己酮为原料，在卤代试剂中生成偕二卤代物或烯基卤代物为主，在有机碱中加入添加剂后，脱卤化氢生成含杂原子环己烯卤代物。此方法工艺简单，避免了传统方法中混合物纯化的操作，产物得到了充分利用。在偕二溴代物类似消除条件下，通过加入添加剂克服了偕二氯代物消除难点，通过不同碱的位阻来达到控制区域选择性的目的。
• [EN] HETEROARYL COMPOUNDS FOR KINASE INHIBITION<br/>[FR] COMPOSÉS HÉTÉROARYLE D'INHIBITION DE LA KINASE
  申请人：ARIAD PHARMA INC

  公开号：WO2015195228A1

  公开（公告）日：2015-12-23

  Compounds and pharmaceutical compositions that modulate kinase activity, including mutant EGFR and mutant HER2 kinase activity, and compounds, pharmaceutical compositions, and methods of treatment of diseases and conditions associated with kinase activity, including mutant EGFRand mutant HER2 activity, are described herein.

  调节激酶活性的化合物和药物组合物，包括突变的EGFR和突变的HER2激酶活性，以及与激酶活性相关的疾病和病况的治疗方法、化合物、药物组合物，包括突变的EGFR和突变的HER2活性，均在本文中描述。
• A Modular Approach to the Synthesis of <i>gem</i>-Disubstituted Cyclopropanes
  作者：Michael R. Harris、Hanna M. Wisniewska、Wenhua Jiao、Xiaochun Wang、James N. Bradow

  DOI：10.1021/acs.orglett.8b00899

  日期：2018.5.18

  Pd-catalyzed Suzuki–Miyaura coupling reaction of geminal bis(boryl)cyclopropanes has been developed. The reaction offers a highly modular approach to the synthesis of tertiary cyclopropylboronic esters. The resulting boronic esters may be further functionalized to afford a range of gem-disubstituted cyclopropanes, which represent an important structural motif in the pharmaceutical industry. Sequential Suzuki–Miyaura

  已经开发了双双（硼基）环丙烷的非对映选择性，Pd催化的Suzuki-Miyaura偶联反应。该反应为叔环丙基硼酸酯的合成提供了一种高度模块化的方法。所得的硼酸酯可以进一步官能化以提供一定范围的宝石-二取代的环丙烷，其代表了制药工业中的重要结构基序。还报道了宝石-双（硼基）环丙烷的顺序Suzuki-Miyaura交叉偶联反应。偶联方案与多种官能化的芳基和杂芳基溴化物兼容。