4-甲基环己烯-1-基硼酸 | 850567-92-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硼酸衍生物
• 中文名称: 4-甲基环己烯-1-基硼酸
• 中文别名: 4-甲基-1-环己烯-1-硼酸；4-甲基环己烯-1-硼酸
• 英文名称: (4-methylcyclohex-1-en-1-yl)boronic acid
• 英文别名: 4-Methylcyclohexen-1-ylboronic acid；(4-methylcyclohexen-1-yl)boronic acid
• CAS: 850567-92-9
• 化学式: C₇H₁₃BO₂
• mdl: MFCD06659857
• 分子量: 139.99
• InChiKey: SJZMIZIVYIOMIW-UHFFFAOYSA-N

物化性质

• 熔点：
  118-124
• 沸点：
  264.8±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)：
  1.29
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.714
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 危险品标志：
  Xi
• 危险性防范说明：
  P233,P260,P261,P264,P271,P280,P302+P352,P304,P304+P340,P305+P351+P338,P312,P321,P332+P313,P337+P313,P340,P362,P403,P403+P233,P405,P501
• 危险性描述：
  H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
4-Methylcyclohexen-1-ylboronic acid
Product Name:
Synonyms: 4-Methyl-1-cyclohexen-1-ylboronic acid

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
Wear protective gloves/protective clothing/eye protection/face protection
P280:
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
4-Methylcyclohexen-1-ylboronic acid
Ingredient name:
CAS number: 850567-92-9

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
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.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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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
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C7H13BO2
Molecular weight: 140.0

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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：

  4-甲基环己烯-1-基硼酸 在 吡啶 、 copper diacetate 、 sodium sulfate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 36.0h， 生成 Methyl 4-[2-(fluoren-9-ylideneamino)-5-methylcyclohexen-1-yl]-3-oxopentanoate
  参考文献：
  名称：

  二烯基羟胺的[3,3]-重排合成1,4-烯氨基酮

  摘要：

  1,4-烯氨基酮的合成是通过将N-烯基硝酮加到缺电子的烯中而生成的二烯基羟胺的[3,3]重排而实现的。该反应所需的温和条件以及由于重排而同时安装的芴基亚胺N-保护基团，避免了1,4-烯氨基酮的自发环化反应形成相应的吡咯，并允许分离和控制这些反应性中间体的不同功能化。讨论了该新方法的优化，范围和耐受性，并证明了该产品可用于合成吡咯，1,4-二酮和呋喃。

  DOI：

  10.1021/ol501230e
• 作为产物：
  描述：

  4-甲基环己-1-烯基硼酸频哪醇酯 在 sodium periodate 、 ammonium acetate 作用下， 以 水 、 丙酮 为溶剂， 反应 48.0h， 生成 4-甲基环己烯-1-基硼酸
  参考文献：
  名称：

  烯基硼酸的双氧合制备α-氧合酮

  摘要：

  二分之二：N-羟基邻苯二甲酰亚胺已实现了烯基硼酸的双加氧反应。分两步进行，涉及烯基硼酸与N-羟基邻苯二甲酰亚胺的醚化，然后进行[3,3]重排。然后可以将双加氧产物水解形成相应的α-羟基酮或α-苯甲酰氧基酮。

  DOI：

  10.1002/anie.201202704

文献信息

• Palladium-Catalyzed Preparation of Weinreb Amides from Boronic Acids and <i>N</i>-Methyl-<i>N</i>-methoxycarbamoyl Chloride
  作者：Ravi Krishnamoorthy、Sang Q. Lam、Christopher M. Manley、R. Jason Herr

  DOI：10.1021/jo902647h

  日期：2010.2.19

  A simple protocol for the synthesis of Weinreb benzamides and α,β-unsaturated Weinreb amides through a palladium-catalyzed cross-coupling reaction between organoboronic acids and N-methoxy-N-methylcarbamoyl chloride has been developed. The method is also applicable to the use of potassium organotrifluoroborates.

  已经开发了通过有机硼酸与N-甲氧基-N-甲基氨基甲酰氯之间的钯催化交叉偶联反应合成Weinreb苯甲酰胺和α，β-不饱和Weinreb酰胺的简单方案。该方法也适用于有机三氟硼酸钾的使用。
• Synthesis of α-oxygenated ketones and substituted catechols via the rearrangement of N-enoxy- and N-aryloxyphthalimides
  作者：Michelle A. Kroc、Aditi Patil、Anthony Carlos、Josiah Ballantine、Stephanie Aguilar、Dong-Liang Mo、Heng-Yen Wang、Daniel S. Mueller、Donald J. Wink、Laura L. Anderson

  DOI：10.1016/j.tet.2017.01.061

  日期：2017.7

  synthesis of α-oxygenated carbonyl compounds and catechols is the treatment of a carbonyl compound or a phenol with an electrophilic oxygen source. As an alternative approach to these important structures, formal [3,3]-rearrangements of N-enoxyphthalimides, N-enoxyisoindolinones, and N-aryloxyphthalimides have been explored. When used in combination with an initial Chan-Lam coupling, these transformations

  合成α-氧化羰基化合物和邻苯二酚的常用方法是用亲电子氧源处理羰基化合物或苯酚。作为这些重要结构的替代方法，已经研究了N-烯氧基邻苯二甲酰亚胺，N-烯氧基异吲哚满酮和N-芳氧基邻苯二甲酰亚胺的形式[3,3]重排。当与初始Chan-Lam偶联结合使用时，这些转化有助于烯基硼酸的双氧合以合成α-加氧的酮和芳基硼酸的双氧合以合成儿茶酚。N-烯氧基异吲哚啉酮的重排也已显示为非对映选择性的。
• 2-Alkyl/alkenyl substituted pyridine C-region analogues of 2-(3-fluoro-4-methylsulfonylaminophenyl)propanamides as highly potent TRPV1 antagonists
  作者：HyungChul Ryu、Sejin Seo、Seong-Hee Cho、Ho Shin Kim、Aeran Jung、Dong Wook Kang、Karam Son、Minghua Cui、Sun-hye Hong、Pankaz Kumar Sharma、Sun Choi、Peter M. Blumberg、Robert Frank-Foltyn、Gregor Bahrenberg、Hannelore Stockhausen、Klaus Schiene、Thomas Christoph、Sven Frormann、Jeewoo Lee

  DOI：10.1016/j.bmcl.2014.05.074

  日期：2014.8

  A series of 2-alkyl/alkenyl pyridine C-region derivatives of 2-(3-fluoro-4-methylsulfonylaminophenyl)propanamides were investigated as hTRPV1 antagonists. Multiple compounds showed excellent and stereospecific TRPV1 antagonism with better potency than previous lead 2. Among them, compound 15f demonstrated a strong analgesic profile in a rat neuropathic pain model and blocked capsaicin-induced hypothermia

  研究了一系列 2-(3-fluoro-4-methylsulfonylaminophenyl)propanamides 的 2-烷基/烯基吡啶 C 区衍生物作为 hTRPV1 拮抗剂。多种化合物显示出优异的立体特异性 TRPV1 拮抗作用，其效力优于先前的铅 2。其中，化合物 15f 在大鼠神经性疼痛模型中表现出强大的镇痛作用，并以剂量​​依赖性方式阻断辣椒素诱导的体温过低。(S)-15f 与我们的 hTRPV1 同源模型的对接分析提供了对其特定结合模式的深入了解。
• Enantioselective hydrogenation of cyclic tetrasubstituted-olefinic dehydroamino acid derivatives
  作者：Feng Wan、Nan Wang、Yuxin Zhu、Chuyan Tang、Jerome Claverie、Wenjun Tang

  DOI：10.1039/d1cc01277k

  日期：——

  An efficient asymmetric hydrogenation of cyclic tetrasubstituted-olefinic dehydroamino acid derivatives has been achieved with a Rh-ArcPhos catalyst, affording a series of α-acylamino-β-alkyl tetrahydropyranones with two contiguous chiral centers in up to 96% ee and 1000 TON.

  使用 Rh-ArcPhos 催化剂实现了环状四取代烯烃脱氢氨基酸衍生物的有效不对称氢化，得到了一系列具有两个连续手性中心的 α-酰基氨基-β-烷基四氢吡喃酮，其 ee 和 1000 TON。
• Isothiazole derivatives as GPR120 agonists for the treatment of type II diabetes
  申请人：Janssen Pharmaceutica NV

  公开号：US09067898B1

  公开（公告）日：2015-06-30

  Disclosed are compounds, compositions and methods for treating of disorders that are affected by the modulation of the GPR120 receptor. Such compounds are represented by Formula (I) as follows: wherein R1, G, and Q are defined herein.

  揭示了一种通过调节GPR120受体来治疗受影响疾病的化合物、组合物和方法。这些化合物由以下式（I）表示：其中R1、G和Q在此处定义。