2-(1-苯基乙烯基)-1,3,2-二氧硼杂环己烷 | 415727-02-5

• 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: 2-(1-苯基乙烯基)-1,3,2-二氧硼杂环己烷
• 英文名称: 2-(1-phenylethenyl)-1,3,2-dioxabornane
• 英文别名: 2-(1-Phenylvinyl)-1,3,2-dioxaborinane；2-(1-phenylethenyl)-1,3,2-dioxaborinane
• CAS: 415727-02-5
• 化学式: C₁₁H₁₃BO₂
• mdl: MFCD11504976
• 分子量: 188.034
• InChiKey: UJNPUKGUVLOFOZ-UHFFFAOYSA-N

物化性质

• 沸点：
  262.4±33.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.87
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P330,P363,P501
• 危险性描述：
  H302,H312,H332

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1-Phenylvinylboronic acid, propanediol cyclic ester
Synonyms: 2-(1-Phenylvinyl)-1,3,2-dioxaborinane

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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-Phenylvinylboronic acid, propanediol cyclic ester
CAS number: 415727-02-5

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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, under −20◦C.
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: C11H13BO2
Molecular weight: 188.0

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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.

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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：

  溴乙酸乙酯 、 2-(1-苯基乙烯基)-1,3,2-二氧硼杂环己烷 在 fac-tris(2-phenylpyridinato-N,C2')iridium(III) 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以40%的产率得到4-氧代-4-苯基丁酸乙酯
  参考文献：
  名称：

  烯基硼酸盐的光催化烷基自由基加成串联氧化

  摘要：

  光催化氧化是一种流行的有机合成转化方式，在学术界和工业界应用广泛。在此，我们报告了蓝光诱导的烷基化-氧化串联反应，通过结合烷基自由基加成和烯基硼酸盐的氧化来合成多种酮。该反应以可接受的收率显示出优异的官能团相容性，并且自由基前体的多样性是适用的。

  DOI：

  10.1021/acs.joc.2c02923
• 作为产物：
  描述：

  alpha- 溴苯乙烯 在 magnesium sulfate 、 magnesium 、 1,2-二溴乙烷 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 1.5h， 生成 2-(1-苯基乙烯基)-1,3,2-二氧硼杂环己烷
  参考文献：
  名称：

  1-苯基乙烯基硼酸和酯的不对称氢化用于合成手性有机硼化合物

  摘要：

  在[Rh（cod）2 ] BF 4-（R）-BINAP（3mol％）的存在下，在氢气气氛（9atm）下，在-20℃下进行乙二醇1-苯基乙烯基硼酸酯的氢化。碱性过氧化氢氧化后，反应生成80％ee的1-苯基乙醇

  DOI：

  10.1016/s0022-328x(01)01239-6

文献信息

• Enantioselective addition of alkenylzinc reagents to aldehydes with organoboronates as the alkenyl source
  作者：Zhuo Chai、Xin-Yuan Liu、Jun-Kang Zhang、Gang Zhao

  DOI：10.1016/j.tetasy.2007.02.026

  日期：2007.4

  Alkenylboronates were used as a vinyl source in the asymmetric addition of an alkenylzinc reagent to aldehydes catalyzed by a dendritic ligand. The resulting allylic alcohol products were obtained in 66–96% ee and 35–64% yields.

  在烯基锌试剂不对称加成由树状配体催化的醛中时，烯基硼酸酯用作乙烯基源。所得的烯丙醇产品以ee 66-96％和35-64％的产率获得。
• Asymmetric hydrogenation of 1-phenylethenylboronic acid and esters for the synthesis of chiral organoboron compounds
  作者：Masato Ueda、Atsushi Saitoh、Norio Miyaura

  DOI：10.1016/s0022-328x(01)01239-6

  日期：2002.1

  The hydrogenation of ethanediol 1-phenylethenylboronic ester was carried out at −20 °C under a hydrogen atmosphere (9 atm) in the presence of [Rh(cod)2]BF4–(R)-BINAP (3 mol%). After alkaline hydrogen peroxide oxidation, the reaction gave 1-phenylethanol with 80% e.e.

  在[Rh（cod）2 ] BF 4-（R）-BINAP（3mol％）的存在下，在氢气气氛（9atm）下，在-20℃下进行乙二醇1-苯基乙烯基硼酸酯的氢化。碱性过氧化氢氧化后，反应生成80％ee的1-苯基乙醇
• Photocatalytic Alkyl Radical Addition Tandem Oxidation of Alkenyl Borates
  作者：Yu-Jie Li、De-Guang Liu、Jin-Hu Ren、Tian-Jun Gong、Yao Fu

  DOI：10.1021/acs.joc.2c02923

  日期：——

  Photocatalytic oxidation is a popular transformation way for organic synthesis and is widely applied in academia and industry. Herein, we report a blue light-induced alkylation–oxidation tandem reaction for the synthesis of diverse ketones by combining alkyl radical addition and oxidation of alkenyl borates. This reaction shows excellent functional group compatibility in acceptable yields, and diversity

  光催化氧化是一种流行的有机合成转化方式，在学术界和工业界应用广泛。在此，我们报告了蓝光诱导的烷基化-氧化串联反应，通过结合烷基自由基加成和烯基硼酸盐的氧化来合成多种酮。该反应以可接受的收率显示出优异的官能团相容性，并且自由基前体的多样性是适用的。