(2-甲基丙基)硼酸(1S,2S,3R,5S)-(+)-2,3-蒎烷二醇酯 | 84110-34-9

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: (2-甲基丙基)硼酸(1S,2S,3R,5S)-(+)-2,3-蒎烷二醇酯
• 中文别名: 异丁基硼酸-(1S,2S,3R,5S)-(+)-2,3-蒎二酯；2-甲基丙烷硼酸-(1S,2S,3R,5S)-(+)-2,3-频二醇酯；(3aS,4S,6S,7aR)-2-异丁基-3a,5,5-三甲基六氢-4,6-桥亚甲基-1,3,2-苯并二氧杂环戊硼烷；(2-甲基丙基)硼酸（1S,2S,3R,5S）-(+)-2,3-蒎烷二醇酯；(+)-蒎烷二醇异丁基硼酸酯；异丁基硼酸(1S,2S,3R,5S)-(+)-2,3-蒎二酯
• 英文名称: 2-(2-methylpropyl)-(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborole
• 英文别名: (3aS,4S,6S,7aR)-3a,5,5-trimethyl-2-(2-methylpropyl)hexahydro-4,6-methano-1,3,2-benzodioxaborole；2-methylpropylboronic acid-(+)-pinanediol ester；iso-butylboronic acid pinanediol ester；(S)-pinanediol-2-methylpropane-1-boronate；(3aS,4S,6S,7aR)-2-(2-methylpropyl)-3a,4,5,6,7,7a-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborole；(3aS,4S,6S,7aR)-2-isobutyl-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborole；(1S,2S,6R,8S)-4-isobutyl-2,9,9-trimethyl-3,5-dioxa-4-bora-tricyclo[6.1.1.0*2,6*]decane；isobutylboronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester；(s)-pinanediol (2-methylpropyl)boronate；(3aS,4S,6S,7aR)-2-Isobutyl-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole；(1S,2S,6R,8S)-2,9,9-trimethyl-4-(2-methylpropyl)-3,5-dioxa-4-boratricyclo[6.1.1.02,6]decane
• CAS: 84110-34-9
• 化学式: C₁₄H₂₅BO₂
• 分子量: 236.162
• InChiKey: QGWQMLAZUPRXGK-FMSGJZPZSA-N

物化性质

• 沸点：
  272.3±9.0℃ (760 Torr)
• 密度：
  0.97±0.1 g/cm3 (20 ºC 760 Torr)
• 闪点：
  118.5±18.7℃

计算性质

• 辛醇/水分配系数(LogP)：
  3.37
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• TSCA：
  No
• 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：
  室温和干燥环境

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 2-Methylpropaneboronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester
Synonyms:

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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: 2-Methylpropaneboronic acid (1S,2S,3R,5S)-(+)-2,3-pinanediol ester
CAS number: 84110-34-9

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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: C14H25BO2
Molecular weight: 236.2

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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：

  (2-甲基丙基)硼酸(1S,2S,3R,5S)-(+)-2,3-蒎烷二醇酯 生成 博特佐米不纯53
  参考文献：
  名称：

  [EN] METHODS FOR PREPARING BORTEZOMIB AND INTERMEDIATES USED IN ITS MANUFACTURE
  [FR] PROCÉDÉ DE PRÉPARATION DU BORTÉZOMIB ET INTERMÉDIAIRES UTILISÉS DANS SA PRÉPARATION

  摘要：

  本文提供了制备硼替佐米和制备硼替佐米的中间体的方法。本方法意外地提供了更高的硼替佐米和制备硼替佐米的中间体的收率和纯度，包括光学纯度。

  公开号：

  WO2009004350A1
• 作为产物：
  描述：

  (+)-α-蒎烯 在 吡啶 、 四氧化锇 、 magnesium sulfate 、 N-甲基吗啉氧化物 作用下， 以 乙醚 、 水 、 叔丁醇 为溶剂， 生成 (2-甲基丙基)硼酸(1S,2S,3R,5S)-(+)-2,3-蒎烷二醇酯
  参考文献：
  名称：

  Expanding the scope of PNA-encoded libraries: divergent synthesis of libraries targeting cysteine, serine and metallo-proteases as well as tyrosine phosphatases

  摘要：

  Seven PNA-encoded combinatorial libraries targeting proteases and phosphatases with covalent reversible and irreversible mechanism-based inhibitors were prepared. The libraries were synthesized using modified PNA monomers, which dramatically increase the water solubility of the libraries in biologically relevant buffers. The libraries were shown to selectively inhibit targeted enzymes. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.03.033
• 作为试剂：
  描述：

  (+)-pinanediol 、 异丁基硼酸 在 (2-甲基丙基)硼酸(1S,2S,3R,5S)-(+)-2,3-蒎烷二醇酯 作用下， 以 正庚烷 、 Brine 为溶剂， 反应 1.0h， 生成 (2-甲基丙基)硼酸(1S,2S,3R,5S)-(+)-2,3-蒎烷二醇酯
  参考文献：
  名称：

  BORTEZOMIB AND PROCESS FOR PRODUCING SAME

  摘要：

  本申请提供了一种制备硼替佐米、其中间体和硼替佐米晶体形式的过程。

  公开号：

  US20100226597A1

文献信息

• Structure-Based Optimization and Discovery of M3258, a Specific Inhibitor of the Immunoproteasome Subunit LMP7 (β5i)
  作者：Markus Klein、Michael Busch、Manja Friese-Hamim、Stefano Crosignani、Thomas Fuchss、Djordje Musil、Felix Rohdich、Michael P. Sanderson、Jeyaprakashnarayanan Seenisamy、Gina Walter-Bausch、Ugo Zanelli、Philip Hewitt、Christina Esdar、Oliver Schadt

  DOI：10.1021/acs.jmedchem.1c00604

  日期：2021.7.22

  acids, which selectively inhibit LMP7 while sparing all other subunits. The exploitation of structural differences between the proteasome subunits culminated in the identification of the highly potent, exquisitely selective, and orally available LMP7 inhibitor 50 (M3258). Based on the strong antitumor activity observed with M3258 in MM models and a favorable preclinical data package, a phase I clinical

  蛋白酶体是泛素依赖性蛋白质降解途径中广泛表达的关键成分，其中包含具有催化活性的亚基（β1、β2 和 β5）。LMP7 (β5i) 是免疫蛋白酶体的一个亚基，是一种主要在造血细胞中表达的诱导型异构体。用于治疗多发性骨髓瘤 (MM) 的临床有效的泛蛋白酶体抑制剂非选择性靶向 LMP7 和组成型蛋白酶体和免疫蛋白酶体的其他亚基，具有相当的效力，这可能会限制这些药物的治疗适用性。在这里，我们描述了新型酰氨基硼酸的发现和基于结构的命中优化，它选择性地抑制 LMP7，同时保留所有其他亚基。对蛋白酶体亚基之间结构差异的开发最终确定了高效能，50 (M3258)。基于 M3258 在 MM 模型中观察到的强大抗肿瘤活性和有利的临床前数据包，在复发/难治性 MM 患者中启动了 I 期临床试验。
• Virtues of Volatility: A Facile Transesterification Approach to Boronic Acids
  作者：Stefan P. A. Hinkes、Christian D. P. Klein

  DOI：10.1021/acs.orglett.9b00584

  日期：2019.5.3

  Boronic acids are an increasingly important compound class for many applications, including C–C bond formation reactions, medicinal chemistry, and diagnostics. The deprotection of boronic ester intermediates is frequently a problematic and inefficient step in boronic acid syntheses. We describe an approach that highly facilitates this transformation by leveraging the volatility of methylboronic acid and

  硼酸对于许多应用而言，都是越来越重要的化合物类别，包括C–C键形成反应，药物化学和诊断学。硼酸酯中间体的脱保护在硼酸合成中通常是一个有问题且效率低下的步骤。我们描述了一种通过利用甲基硼酸及其二醇酯的挥发性极大地促进这种转变的方法。该方法在温和条件下进行，提供了高收率，并且消除了繁琐且麻烦的纯化步骤。
• Proteasome inhibitors and methods of using the same
  申请人：Bernardini Raffaella

  公开号：US20060189806A1

  公开（公告）日：2006-08-24

  The present invention provides boronic acid compounds, boronic esters, and compositions thereof that can modulate apoptosis such as by inhibition of proteasome activity. The compounds and compositions can be used in methods of inducing apoptosis and treating diseases such as cancer and other disorders associated directly or indirectly with proteasome activity.

  本发明提供了硼酸化合物、硼酸酯及其组合物，可以调节细胞凋亡，例如通过抑制蛋白酶体活性。这些化合物和组合物可用于诱导细胞凋亡和治疗癌症等疾病，以及与蛋白酶体活性直接或间接相关的其他疾病。
• Observations on the Deprotection of Pinanediol and Pinacol Boronate Esters via Fluorinated Intermediates
  作者：Steven R. Inglis、Esther C. Y. Woon、Amber L. Thompson、Christopher J. Schofield

  DOI：10.1021/jo901930v

  日期：2010.1.15

  pinacol esters of various boronic acids via fluoroborane intermediates were evaluated. Treatment of the boronate esters with potassium hydrogen difluoride normally gives trifluoroborate salts; in the case of α-amido alkyl or o-amido phenyl boronate esters, aqueous workup gives difluoroboranes. Procedures for transformation of both trifluoroborates and difluoroboranes to free boronic acids are described.

  评估了通过氟硼烷中间体对各种硼酸的pin二醇和频哪醇酯进行脱保护的方法。用二氟化氢钾处理硼酸酯通常会得到三氟硼酸盐。在α-氨基烷基或邻氨基苯基硼酸酯的情况下，水后处理得到二氟硼烷。描述了将三氟硼酸酯和二氟硼烷转化为游离硼酸的方法。
• Design, synthesis and docking studies of novel dipeptidyl boronic acid proteasome inhibitors constructed from αα- and αβ-amino acids
  作者：Jingmiao Shi、Meng Lei、Wenkui Wu、Huayun Feng、Jia Wang、Shanshan Chen、Yongqiang Zhu、Shihe Hu、Zhaogang Liu、Cheng Jiang

  DOI：10.1016/j.bmcl.2016.03.007

  日期：2016.4

  series of novel dipeptidyl boronic acid proteasome inhibitors constructed from αα- and αβ-amino acids were designed and synthesized. Their structures were elucidated by 1H NMR, 13C NMR, LC–MS and HRMS. These compounds were evaluated for their β5 subunit inhibitory activities of human proteasome. The results showed that dipeptidyl boronic acid inhibitors composed of αα-amino acids were as active as bortezomib

  设计并合成了一系列由αα-和αβ-氨基酸构建的新型二肽基硼酸蛋白酶体抑制剂。通过1 H NMR，13 C NMR，LC-MS和HRMS阐明了它们的结构。评价这些化合物对人蛋白酶体的β5亚基抑制活性。结果表明，由αα-氨基酸组成的二肽基硼酸抑制剂的活性与硼替佐米相同。有趣的是，那些衍生自αβ-氨基酸的酶的活性完全丧失了。在所有抑制剂中，化合物22（IC 50  = 4.82 nM）对蛋白酶体活性的抑制作用最强。化合物22还是对三种具有IC 50的MM细胞系最有活性的在抑制细胞生长试验中，其值小于5 nM。分子对接研究表明，22个蛋白非常适合蛋白酶体的β5亚基活性口袋。