反式-3-(四氢吡喃-2-基氧基)丙烯-1-基硼酸频那醇酯 | 642066-70-4

• 物质功能分类: 化学试剂 - 有机试剂 - 硼酸
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 中文名称: 反式-3-(四氢吡喃-2-基氧基)丙烯-1-基硼酸频那醇酯
• 中文别名: 2-[3-（4,4,5,5-四甲基-[1,3,2]二氧杂硼硼烷-2-基）-烯丙氧基]-四氢吡喃
• 英文名称: (E)-4,4,5,5-tetramethyl-2-(3-((tetrahydro-2H-pyran-2-yl)oxy)prop-1-en-1-yl)-1,3,2-dioxaborolane
• 英文别名: 2-[3-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-YL)-allyloxy]-tetrahydro-pyran；4,4,5,5-tetramethyl-2-[(E)-3-(oxan-2-yloxy)prop-1-enyl]-1,3,2-dioxaborolane
• CAS: 642066-70-4
• 化学式: C₁₄H₂₅BO₄
• 分子量: 268.161
• InChiKey: MHSOBXCZCRNELG-VQHVLOKHSA-N

物化性质

• 沸点：
  323.0±52.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.72
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P312,P305+P351+P338,P280,P302+P352,P304+P340
• 危险性描述：
  H315,H319,H335

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: trans-3-(Tetrahydropyran-2-yloxy)propen-1-ylboronic acid, pinacol ester
Synonyms: Trans-2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)allyoxy]tetrahydropyran

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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: trans-3-(Tetrahydropyran-2-yloxy)propen-1-ylboronic acid, pinacol ester
CAS number: 642066-70-4

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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: C14H25BO4
Molecular weight: 268.2

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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：

  反式-3-(四氢吡喃-2-基氧基)丙烯-1-基硼酸频那醇酯 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以65%的产率得到反式-3-羟基丙烯硼酸频哪酯
  参考文献：
  名称：

  使用B（pin）取代的亲电试剂的无环酯的对映选择性α-烯丙基化：通过Pd / Lewis碱催化的立体控制元素的独立调节

  摘要：

  Lewis碱和Pd催化剂之间的配合可使用双官能团B（pin）取代的亲电试剂对芳基和乙烯基乙酸酯进行直接对映选择性α-官能化。认识到两种催化剂都可以控制必要的立体化学方面，是该方法成功的关键。Lewis碱催化剂控制反应的对映选择性，而Pd催化剂调节烯基-B（pin）构型。这是在Pd催化的烯丙基烷基化过程中使用协同催化控制两个立体化学特征的第一个例子。

  DOI：

  10.1002/chem.201803543
• 作为产物：
  描述：

  哌喃 、 频那醇硼烷 在 bis(cyclohexanyl)borane 作用下， 以 neat (no solvent) 为溶剂， 反应 30.0h， 以46%的产率得到反式-3-(四氢吡喃-2-基氧基)丙烯-1-基硼酸频那醇酯
  参考文献：
  名称：

  使用B（pin）取代的亲电试剂的无环酯的对映选择性α-烯丙基化：通过Pd / Lewis碱催化的立体控制元素的独立调节

  摘要：

  Lewis碱和Pd催化剂之间的配合可使用双官能团B（pin）取代的亲电试剂对芳基和乙烯基乙酸酯进行直接对映选择性α-官能化。认识到两种催化剂都可以控制必要的立体化学方面，是该方法成功的关键。Lewis碱催化剂控制反应的对映选择性，而Pd催化剂调节烯基-B（pin）构型。这是在Pd催化的烯丙基烷基化过程中使用协同催化控制两个立体化学特征的第一个例子。

  DOI：

  10.1002/chem.201803543

文献信息

• [EN] EIF4E-INHIBITING 4-OXO-3,4-DIHYDROPYRIDO[3,4-D]PYRIMIDINE COMPOUNDS<br/>[FR] COMPOSÉS DE 4-OXO-3,4-DIHYDROPYRIDO[3,4-D]PYRIMIDINE INHIBANT EIF4E
  申请人：EFFECTOR THERAPEUTICS INC

  公开号：WO2021003157A1

  公开（公告）日：2021-01-07

  The present invention provides synthesis, pharmaceutically acceptable formulations and uses of compounds in accordance with Formula I, or a stereoisomer, tautomer or pharmaceutically acceptable salt thereof. For Formula I compounds X1, X2, X3, X4, X5, X6, Q, L1, L2, Y, R1, R2, R3, R4, R5, R6, R7, R8 and rings A, B and C are as defined in the specification. The inventive Formula I compounds are inhibitors of eIF4e and find utility in any number of therapeutic applications, including but not limited to treatment of inflammation and various cancers.

  本发明提供了根据式I合成的化合物、药用可接受的配方和用途，或其立体异构体、互变异构体或药用可接受的盐。对于式I化合物，X1、X2、X3、X4、X5、X6、Q、L1、L2、Y、R1、R2、R3、R4、R5、R6、R7、R8和环A、B和C的定义如规范中所述。创新的式I化合物是eIF4e的抑制剂，并在许多治疗应用中发挥作用，包括但不限于治疗炎症和各种癌症。
• [EN] SUBSTITUTED 1,2,3-TRIAZOLES AS NR2B-SELECTIVE NMDA MODULATORS<br/>[FR] 1,2,3-TRIAZOLES SUBSTITUÉS UTILISÉS COMME MODULATEURS DE NMDA SÉLECTIFS DE NR2B
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2017139428A1

  公开（公告）日：2017-08-17

  Substituted 1,2,3-triazoles as NR2B receptor ligands. Such compounds may be used in NR2B receptor modulation and in pharmaceutical compositions and methods for the treatment of disease states, disorders, and conditions mediated by NR2B receptor activity.

  1,2,3-三唑作为NR2B受体配体。这类化合物可用于NR2B受体调节以及用于治疗由NR2B受体活性介导的疾病状态、紊乱和病况的药物组合物和方法。
• Total Synthesis and Biological Evaluation of Amphidinolide V and Analogues
  作者：Alois Fürstner、Susanne Flügge、Oleg Larionov、Yohei Takahashi、Takaaki Kubota、Jun'ichi Kobayashi

  DOI：10.1002/chem.200802068

  日期：2009.4.14

  The awesome power of metathesis is illustrated by a concise synthesis of the extremely scarce marine natural product amphidinolide V, which hinges on a sequence of ring‐closing alkyne metathesis followed by intermolecular enyne metathesis with ethylene (see scheme). As a complete set of conceivable stereoisomers was prepared, the constitution and absolute configuration of this macrolide could be established

  简而言之，极其稀少的海洋天然产物两性化合物Amphidinolide V的合成说明了复分解的强大功能，该合成取决于一系列闭环炔烃复分解，然后是乙烯间的分子间烯炔复分解（参见方案）。制备了一套完整的可能的立体异构体后，即可确定该大环内酯的组成和绝对构型，并首次了解了控制其细胞毒性的结构-活性关系。
• [EN] SUBSTITUTED N-(1H-INDAZOL-4-YL)IMIDAZO[1, 2-A]PYRIDINE-3- CARBOXAMIDE COMPOUNDS AS CFMS INHIBITORS<br/>[FR] COMPOSÉS À BASE DE N-(1H-INDAZOL-4-YL)IMIDAZO[1,2-A]PYRIDINE-3-CARBOXAMIDE SUBSTITUÉ UTILES EN TANT QU'INHIBITEURS DE CFMS
  申请人：ARRAY BIOPHARMA INC

  公开号：WO2011079076A1

  公开（公告）日：2011-06-30

  Compounds of Formula (I): and pharmaceutically acceptable salts thereof in which R1, R2, R3, R4 and R5 have the meanings given in the specification, are inhibitors of cFMS and are useful in the treatment of bone-related diseases, cancer, autoimmune disorders, inflammatory diseases, cardiovascular diseases and pain.

  式(I)的化合物及其药学上可接受的盐，其中R1、R2、R3、R4和R5的含义如规范中所述，是cFMS的抑制剂，并且在治疗与骨相关的疾病、癌症、自身免疫性疾病、炎症性疾病、心血管疾病和疼痛方面是有用的。
• Preparation of (<i>E</i>)-1-Alkenylboronic Acid Pinacol Esters via Transfer of Alkenyl Group from Boron to Boron
  作者：Masayuki Hoshi、Kazuya Shirakawa、Akira Arase

  DOI：10.1055/s-2004-829165

  日期：——

  (E)-1-alkenylboronic acid pinacol esters 3 were investigated. Hydroboration of 1-alkynes I with 1,3,2-benzodioxaborole (catecholborane), in situ generated by the reaction of BH 3 in THF with catechol, proceeded in the presence of a catalytic amount of dicyclohexylborane in THF at room temperature to give the corresponding (E)-1-alkenylboronic acid catechol esters 2. Treatment of the resultant esters 2 with 2,3-dimethyl-2

  研究了 (E)-1-烯基硼酸频哪醇酯 3 的两种合成路线。1-炔烃 I 与 1,3,2-苯并二恶硼烷（儿茶酚硼烷）的硼氢化反应是在 THF 中的 BH 3 与儿茶酚反应生成的，在 THF 中催化量的二环己基硼烷存在下，室温下进行，得到相应的 (E)-1-烯基硼酸儿茶酚酯 2. 用 2,3-二甲基-2,3-丁二醇 (频哪醇) 处理所得酯 2 容易得到所需产物 3，其对空气、水分和色谱不敏感，整体产量好到高。顺序反应是以一锅方式从THF中的BH 3 到3的高效途径。或者，用 4,4,5,5-四甲基-1,3 对 1 进行硼氢化，2-二氧硼烷（频哪醇硼烷）是在催化量的二环己基硼烷的存在下在室温下在纯净条件下获得的，以良好至极好的产率直接提供相应的产物 3。从充分利用频哪醇硼烷和不使用溶剂的角度来看，该路线非常有效且对环境无害，并且能够使用多种炔烃1，包括官能化的炔烃1，例如HCCCH 2 Cl和HCCCH