4-硼酸酯-苯乙酸甲酯 | 454185-98-9

• 物质功能分类: 化学试剂 - 有机试剂 - 硼酸酯
• 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: 4-硼酸酯-苯乙酸甲酯
• 中文别名: (4-甲氧基羰基甲基)苯硼酸频那醇酯；(4-甲氧基酰基甲基苯基)硼酸频哪醇酯
• 英文名称: methyl [4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetate
• 英文别名: methyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate；methyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenyl)acetate；methyl 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetate
• CAS: 454185-98-9
• 化学式: C₁₅H₂₁BO₄
• 分子量: 276.14
• InChiKey: NBPODFADVLNXKO-UHFFFAOYSA-N

物化性质

• 熔点：
  41-45 °C
• 沸点：
  363.0±25.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)
• 溶解度：
  溶于甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2931900090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温且干燥

SDS

Material Safety Data Sheet

---

Section 1. Identification of the substance
Product Name: (4-Methoxycarbonylmethyl)phenylboronic acid pinacol ester
Synonyms:

---

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

---

Section 3. Composition/information on ingredients.
Ingredient name: (4-Methoxycarbonylmethyl)phenylboronic acid pinacol ester
CAS number: 454185-98-9

---

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, refrigerated.
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: C15H21BO4
Molecular weight: 276.1

---

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

---

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

用途

4-硼酸酯-苯乙酸甲酯作为硼酸衍生物，在有机合成过程中可用作Suzuki交叉偶联反应的重要原料。

制备

将3.0克（8.85毫摩尔）七水合磷酸钾、1.50克（5.90毫摩尔）联硼酸频哪醇酯B2(pin)2、12毫克（0.015毫摩尔）Xphos-Pd-G2和4毫克（0.008毫摩尔）Xphos依次加入反应瓶中，加入6毫升乙醇搅拌均匀。随后加入4-溴苯乙酸甲酯，在室温下反应1小时。

将反应液用5毫升乙酸乙酯稀释后进行硅藻土过滤，并用乙酸乙酯洗涤。合并滤液并减压浓缩得到粗产物。通过硅胶柱层析分离，使用石油醚-乙酸乙酯洗脱，得到4-硼酸酯-苯乙酸甲酯粗品。最后，利用体积分数20%的乙醇进行重结晶，即得纯化的4-硼酸酯-苯乙酸甲酯。

反应信息

• 作为反应物：
  描述：

  4-硼酸酯-苯乙酸甲酯 在 4-乙酰氨基苯磺酰叠氮 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以81%的产率得到methyl 2-diazo-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetate
  参考文献：
  名称：

  铑（II）-和钯（II）催化反应的互补反应性的多样性合成

  摘要：

  铑（II）催化的重氮芳基乙酸酯反应可以在碘化物，三氟甲磺酸酯，有机硼和有机锡烷官能团的存在下进行，从而形成具有高立体选择性的多种环丙烷或CH插入产物。铑（II）催化的反应与随后的钯（II）催化的Suzuki偶联的结合为多样性合成提供了一种新颖的策略。

  DOI：

  10.1021/jo060636u
• 作为产物：
  描述：

  4-羟基苯乙酸甲酯 在 2,6-二甲基吡啶 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium acetate 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 生成 4-硼酸酯-苯乙酸甲酯
  参考文献：
  名称：

  （-）-tejedine的第一个对映选择性全合成。

  摘要：

  [结构：见正文]报告了（-）-tejedine（1）的第一个对映选择性全合成。Tejedine是一种1998年从小Ber小isolated中提取的次要成分的癸二双苄基四氢异喹啉。合成是通过采用四个关键步骤的策略实现的，包括手性辅助非对映选择性Bischler-Napieralski环化。

  DOI：

  10.1021/ol0261635

文献信息

• Synthesis of Ketones and Esters from Heteroatom-Functionalized Alkenes by Cobalt-Mediated Hydrogen Atom Transfer
  作者：Xiaoshen Ma、Seth B. Herzon

  DOI：10.1021/acs.joc.6b01709

  日期：2016.10.7

  Cobalt bis(acetylacetonate) is shown to mediate hydrogen atom transfer to a broad range of functionalized alkenes; in situ oxidation of the resulting alkylradical intermediates, followed by hydrolysis, provides expedient access to ketones and esters. By modification of the alcohol solvent, different alkyl ester products may be obtained. The method is compatible with a number of functional groups including

  已显示双（乙酰丙酮酸）钴介导氢原子转移到各种官能化烯烃中。所得烷基自由基中间体的原位氧化，然后水解，可方便地获得酮和酯。通过改性醇溶剂，可以获得不同的烷基酯产物。该方法与许多官能团兼容，包括链烯基卤化物，硫化物，三氟甲磺酸酯和膦酸酯，为乙烯基硅烷的Tamao-Fleming氧化和Arndt-Eistert同系物提供了温和而实用的替代方法。
• <scp>Pd‐Catalyzed Site‐Selective</scp> Borylation of Simple Arenes <i>via</i> Thianthrenation ^†
  作者：Xiao‐Yue Chen、Yu‐Hao Huang、Jian Zhou、Peng Wang

  DOI：10.1002/cjoc.202000212

  日期：2020.11

  Site‐selective borylation of simple arenes was realized in one pot via an electrophilic thianthrenation/Pd‐catalyzed borylation sequence. The key to achieve this operatically simple process is the use of Pd catalysis, which could tolerate the solvent and acidic conditions used in the thianthrenation step. This protocol features mild conditions, broad functional group tolerance, and simple manipulations

  简单的芳烃的位点选择性硼化通过亲电子的thththrenation / Pd催化的硼化序列实现。实现这种操作上简单的过程的关键是使用Pd催化，该催化可以耐受在thththrenation步骤中使用的溶剂和酸性条件。该方案具有温和的条件，宽泛的官能团耐受性和简单的操作方法，适用于各种药物和复杂的生物活性分子的后期功能化。
• [EN] BORON-CONTAINING RHO KINASE INHIBITORS<br/>[FR] INHIBITEURS DE LA RHO KINASE CONTENANT DU BORE
  申请人：PERCIPIAD INC

  公开号：WO2021011873A1

  公开（公告）日：2021-01-21

  The present invention provides boron-containing isoquinoline compounds as protein kinase-modulating compounds. These compounds are useful as neuroprotective and neuro-regenerative agents for the amelioration of glaucoma and other ocular neuropathies.

  本发明提供了含硼的异喹啉化合物作为蛋白激酶调节化合物。这些化合物可用作神经保护和神经再生剂，用于改善青光眼和其他眼神经病变。
• Catalytic Enantio- and Diastereoselective Cyclopropanation of 2-Azadienes for the Synthesis of Aminocyclopropanes Bearing Quaternary Carbon Stereogenic Centers
  作者：Xinxin Shao、Steven J. Malcolmson

  DOI：10.1021/acs.orglett.9b02692

  日期：2019.9.20

  We report the catalytic enantio- and diastereoselective preparation of aminocyclopropanes by the cyclopropanation of terminal and (Z)-internal 2-azadienes with donor/acceptor carbenes derived from α-diazoesters. The resulting cyclopropanes bear quaternary carbon stereogenic centers vicinal to the amino-substituted carbon and are formed as a single diastereomer in up to 99:1 er and 97% yield with 0

  我们报道了通过末端和( Z )-内部2-氮杂二烯与源自α-重氮酯的供体/受体卡宾的环丙烷化，催化对映和非对映选择性制备氨基环丙烷。所得环丙烷带有与氨基取代碳相邻的季碳立构中心，并以高达 99:1 er 和 97% 产率形成单一非对映异构体，其中使用 0.5 mol% 的 Rh 2 (DOSP) 4 和仅1.5当量的重氮试剂。内部氮杂二烯的转化提供了具有三个连续立体中心的环丙烷。
• NOVEL PYRIMIDINE DERIVATIVE AND PHARMACEUTICAL COMPOSITION INCLUDING SAME AS AN ACTIVE INGREDIENT
  申请人：Hanmi Pharmaceutical Co., Ltd.

  公开号：EP2738174A2

  公开（公告）日：2014-06-04

  The present invention relates to a compound represented by formula (I) for inhibiting the activity of diacylglycerol O-acyltransferase type 1 (DGAT1), and pharmaceutically acceptable salts thereof, and a pharmaceutical composition comprising same as an active ingredient. The compound of the present invention may be used effectively in the treatment or prevention of a disease or condition mediated by the activity of DGAT1 such as obesity, type II diabetes, dyslipidemia, metabolic syndrome, and the like, without any adverse effects: wherein A, B, X, and R5 to R7 are the same as defined in the specification.

  本发明涉及一种化合物，其由式(I)表示，用于抑制二酰基甘油酰基转移酶1型（DGAT1）的活性，以及其药学上可接受的盐，以及包含其作为活性成分的药物组合物。本发明的化合物可以有效用于治疗或预防由DGAT1活性介导的疾病或病况，如肥胖、2型糖尿病、血脂异常、代谢综合征等，而不产生任何不良影响： 其中A、B、X和R5到R7与规范中定义的相同。