5,5-二甲基-2-(1-苯基乙烯基)-1,3,2-二氧硼杂环己烷 | 938080-25-2

• 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: 5,5-二甲基-2-(1-苯基乙烯基)-1,3,2-二氧硼杂环己烷
• 中文别名: 1-苯基乙烯基硼酸,新戊二醇酯
• 英文名称: 5,5-dimethyl-2-(1-phenylvinyl)-1,3,2-dioxaborinane
• 英文别名: 5,5-dimethyl-2-(1-phenylethenyl)-1,3,2-dioxaborinane
• CAS: 938080-25-2
• 化学式: C₁₃H₁₇BO₂
• 分子量: 216.088
• InChiKey: HNJLVOQORSGCLB-UHFFFAOYSA-N

物化性质

• 沸点：
  130 °C(Press: 1.0 Torr)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 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
• 储存条件：
  存储条件：2-8°C，密封，干燥

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 1-Phenylvinylboronic acid, neopentyl glycol ester
Synonyms: 5,5-Dimethyl-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, neopentyl glycol ester
CAS number: 938080-25-2

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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: C13H17BO2
Molecular weight: 216.1

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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.

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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：

  5,5-二甲基-2-(1-苯基乙烯基)-1,3,2-二氧硼杂环己烷 、 二氧化碳 在 [Ni(N,N'-bis[2,6-bis(diphenylmethyl)-4-methylphenyl]imidazole-2-ylidene)(allyl)Cl] 、 potassium tert-butylate 、 盐酸 作用下， 以 甲苯 、 水 、 乙酸乙酯 为溶剂， 20.0~100.0 ℃ 、101.33 kPa 条件下， 反应 15.0h， 以75%的产率得到2-苯基丙烯酸
  参考文献：
  名称：

  Nickel-catalysed carboxylation of organoboronates

  摘要：

  已经开发了一种镍/N-杂环碱（NHC）催化的芳基、杂芳基和烯基硼酸盐的羧化反应，生成相应的羧酸。该转化在一个大气压的二氧化碳下进行，适用于广泛的底物，并表现出良好的官能团兼容性。

  DOI：

  10.1039/c4cc03650f
• 作为产物：
  描述：

  1-苯基乙烯基硼酸 、 2,2-二甲基-1,3-丙二醇 以 乙醚 为溶剂， 生成 5,5-二甲基-2-(1-苯基乙烯基)-1,3,2-二氧硼杂环己烷
  参考文献：
  名称：

  钌催化碳-杂原子键的非常规化学选择性裂解，使芳香族酮单烯基化

  摘要：

  的钌催化选择性monoalkenylation邻ç  O或C 达到Ñ芳族酮的键。该反应可以直接比较不同碳-杂原子键裂解的相对反应性，因此表明具有非常规的化学选择性，较小的，供电子更多的基团更易于裂解。的Ç选择性monofunctionalization 在存在O键邻Ç  H键也被实现。

  DOI：

  10.1002/anie.201503641

文献信息

• Nickel-Catalyzed 1,2-Carboamination of Alkenyl Alcohols
  作者：Taeho Kang、Nana Kim、Peter T. Cheng、Hao Zhang、Klement Foo、Keary M. Engle

  DOI：10.1021/jacs.1c07112

  日期：2021.9.1

  An alcohol-directed, nickel-catalyzed three-component umpolung carboamination of unactivated alkenes with aryl/alkenylboronic esters and electrophilic aminating reagents is reported. This transformation is enabled by specifically tailored O-(2,6-dimethoxybenzoyl)hydroxylamine electrophiles that suppress competitive processes, including undesired β-hydride elimination and transesterification between

  报道了未活化烯烃与芳基/烯基硼酸酯和亲电子胺化试剂的醇导向、镍催化的三组分 umpolung 碳胺化反应。这种转化是通过专门定制的O -(2,6-二甲氧基苯甲酰基)羟胺亲电试剂实现的，该试剂抑制竞争过程，包括不需要的 β-氢化物消除和醇底物和亲电试剂之间的酯交换。该反应提供了所需的 1,2- 碳胺化产物，通常具有高区域和合成-非对映选择性，并表现出广泛的偶联伙伴和烯烃，包括复杂的天然产物。X 射线晶体学分析证实，各种机械实验和环状烯烃底物立体化学结果分析支持有机镍 (I) 物种的醇定向同步插入。
• Nickel‐Catalyzed Regioselective Alkenylarylation of γ,δ‐Alkenyl Ketones via Carbonyl Coordination
  作者：Roshan K. Dhungana、Vivek Aryal、Doleshwar Niroula、Rishi R. Sapkota、Margaret G. Lakomy、Ramesh Giri

  DOI：10.1002/anie.202104871

  日期：2021.8.23

  which enabled us to difunctionalize unactivated γ,δ-alkenes in ketones with alkenyl triflates and arylboronic esters. The reaction was made feasible by the use of 5-chloro-8-hydroxyquinoline as a ligand along with NiBr2⋅DME as a catalyst and LiOtBu as base. The reaction proceeded with a wide range of cyclic, acyclic, endocyclic and exocyclic alkenyl ketones, and electron-rich and electron-deficient arylboronate

  我们公开了镍催化的反应，该反应使我们能够用三氟甲磺酸烯基酯和芳基硼酸酯对酮中未活化的γ,δ-烯烃进行双官能化。通过使用 5-氯-8-羟基喹啉作为配体以及 NiBr 2· DME 作为催化剂和 LiO t Bu 作为碱，使该反应变得可行。该反应适用于各种环状、无环、环内和环外烯基酮，以及富电子和缺电子芳基硼酸酯。该反应也适用于环状和无环烯基三氟甲磺酸酯。对照实验表明反应的进行需要羰基配位。
• Regioselective Alkenylation of Aromatic Ketones with Alkenylboronates Using a RuH₂(CO)(PPh₃)₃ Catalyst via Carbon−Hydrogen Bond Cleavage
  作者：Satoshi Ueno、Naoto Chatani、Fumitoshi Kakiuchi

  DOI：10.1021/jo070182g

  日期：2007.4.1

  The ruthenium-catalyzed alkenylation of C−H bonds with alkenylboronates has been explored for a series of aromatic ketones. The coupling reaction of pivalophenone (1) with 2-isopropenyl-5,5-dimethyl[1,3,2]dioxaborinane (2) gave the corresponding isopropenylation product in 73% yield. In the case of the reaction of a sterically congested alkenylboronate, such as 2-methylpropenylboronate (8), the yield

  对于一系列芳族酮，已经探索了钌与链烯基硼酸酯催化的CH键的烯基化反应。新戊苯甲酮（1）与2-异丙烯基-5,5-二甲基[1,3,2]二氧杂硼烷（2）的偶联反应以73％的收率得到相应的异丙烯基化产物。在空间上拥挤的烯基硼酸酯如2-甲基丙烯基硼酸酯（8）反应的情况下，收率略有降低。当使用β-苯乙烯基硼酸酯时，以良好的产率获得了相应的偶联产物。苯乙酮与α-苯乙烯基硼酸酯的反应仅提供相应的1：1偶联产物。
• Three-Component Asymmetric Ni-Catalyzed 1,2-Dicarbofunctionalization of Unactivated Alkenes via Stereoselective Migratory Insertion
  作者：Omar Apolinar、Taeho Kang、Turki M. Alturaifi、Pranali G. Bedekar、Camille Z. Rubel、Joseph Derosa、Brittany B. Sanchez、Quynh Nguyen Wong、Emily J. Sturgell、Jason S. Chen、Steven R. Wisniewski、Peng Liu、Keary M. Engle

  DOI：10.1021/jacs.2c06636

  日期：2022.10.26

  asymmetric 1,2-dicarbofunctionalization of unactivated alkenes with aryl iodides and aryl/alkenylboronic esters under nickel/bioxazoline catalysis is disclosed. A wide array of aryl and alkenyl nucleophiles are tolerated, furnishing the products in good yield and with high enantioselectivity. In addition to terminal alkenes, 1,2-disubstituted internal alkenes participate in the reaction, establishing two contiguous

  公开了在镍/生物恶唑啉催化下未活化烯烃与芳基碘化物和芳基/烯基硼酸酯的不对称 1,2-二碳官能化。可以耐受多种芳基和烯基亲核试剂，以良好的收率和高对映选择性提供产品。除了末端烯烃外，1,2-二取代的内部烯烃也参与反应，建立两个连续的立体中心，具有高非对映选择性和中等对映选择性。实验和计算技术的结合揭示了催化转化的机制，指向具有对映体决定迁移插入步骤的闭壳途径，
• Protoboration of Alkynes and Miyaura Borylation Catalyzed by Low Loadings of Palladium
  作者：Lei Xu、Zheng Dong、Qi Zhang、Ning Deng、Shi-Yu Li、Hua-Jian Xu

  DOI：10.1021/acs.joc.2c01649

  日期：2022.11.4

  The versions of Miyaura borylation and protoboration of alkynes catalyzed by low loadings of palladium (400 mol ppm = 0.04 mol %) have been developed. These transformations have a broad substrate scope, good functional-group compatibility, and gram-scale synthetic ability.

  已经开发出由低负载钯（400 mol ppm = 0.04 mol %）催化的 Miyaura 硼酸化和炔烃原硼化的版本。这些转化具有广泛的底物范围、良好的官能团相容性和克级合成能力。