2-(3-甲氧基-1-丙炔-1-基)-4,4,5,5-四甲基-(1,3,2)二氧杂硼烷 | 634196-63-7

• 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: 2-(3-甲氧基-1-丙炔-1-基)-4,4,5,5-四甲基-(1,3,2)二氧杂硼烷
• 中文别名: 3-甲氧基-1-丙炔-1-基硼酸频哪醇酯；3-甲氧基-1-丙炔-1-硼酸频那醇酯
• 英文名称: 2-(3-methoxyprop-1-yn-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• 英文别名: 3-methoxy-1-propyn-1-ylboronic acid pinacol ester；2-(3-methoxyprop-1-ynyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 634196-63-7
• 化学式: C₁₀H₁₇BO₃
• mdl: MFCD08705273
• 分子量: 196.054
• InChiKey: BJDZPOHVHLSGDP-UHFFFAOYSA-N

物化性质

• 沸点：
  196.2±42.0 °C(Predicted)
• 密度：
  0.982 g/mL at 25 °C
• 闪点：
  170°C

计算性质

• 辛醇/水分配系数(LogP)：
  2.36
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2931900090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
Product Name: 3-Methoxy-1-propyn-1-ylboronic acid, pinacol ester
Synonyms: 2-(3-Methoxy-1-propyn-1-yl)-4,4,5,5-tetramethyl-(1,3,2)dioxaborolane

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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: 3-Methoxy-1-propyn-1-ylboronic acid, pinacol ester
CAS number: 634196-63-7

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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: C10H17BO3
Molecular weight: 196.1

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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

制备方法与用途

炔基硼酸酯可用于多种区域选择性和立体选择性的碳-碳键形成过程，包括烯炔的交叉复分解反应和Alder烯反应。1,2

反应信息

• 作为反应物：
  描述：

  2-(3-甲氧基-1-丙炔-1-基)-4,4,5,5-四甲基-(1,3,2)二氧杂硼烷 在 copper diacetate 作用下， 以 various solvent(s) 为溶剂， 反应 12.0h， 以71%的产率得到1,6-dimethoxyhexa-2,4-diyne
  参考文献：
  名称：

  铜盐介导的炔基硼酸酯的均偶联反应合成对称的1,3-丁二炔

  摘要：

  炔基硼酸酯用作各种π-共轭有机化合物的实用且通用的前体。在Cu（I）或Cu（II）盐的存在下，炔烃硼酸酯暴露于空气后，在质子惰性极性溶剂（如DMI）中容易转化为相应的1,3-二炔。

  DOI：

  10.1016/j.tetlet.2005.10.056
• 作为产物：
  描述：

  异丙醇频哪醇硼酸酯 、 3-methoxy-1-propyn-1-yllithium 生成 2-(3-甲氧基-1-丙炔-1-基)-4,4,5,5-四甲基-(1,3,2)二氧杂硼烷
  参考文献：
  名称：

  Boron-Directed Regio- and Stereoselective Enyne Cross Metathesis:  Efficient Synthesis of Vinyl Boronate Containing 1,3-Dienes

  摘要：

  Regio- and stereoselective enyne cross metathesis reactions between borylated alkynes and terminal alkenes were realized to provide a variety of functionalized vinyl boronates. High chemical yield and regioselectivity was achieved irrespective of substituents on the alkyne and alkene counterparts, whereas Z/E-selectivity was found to be dependent upon the substituents both on the alkyne and alkene.

  DOI：

  10.1021/ol050542r

文献信息

• Alkynylboration Reaction Leading to Boron-Containing π-Extended <i>cis</i>-Stilbenes as a Highly Tunable Fluorophore
  作者：Marina Nogami、Keiichi Hirano、Kensuke Morimoto、Masaru Tanioka、Kazunori Miyamoto、Atsuya Muranaka、Masanobu Uchiyama

  DOI：10.1021/acs.orglett.9b01132

  日期：2019.5.3

  An unprecedented boron-containing fluorophore, π-extended cis-stilbene, obtained via alkynylboration reaction of alkynamide is reported. Boron-containing π-extended cis-stilbenes emit fluorescence with high quantum yields in the solid state and exhibit aggregation-induced emission enhancement. The broad substrate scope of the alkynylboration reaction offers facile access to electronically diverse structures

  报道了通过炔基酰胺的炔基硼化反应获得的空前的含硼荧光团，π-扩展的顺式-sti。含硼的π扩展的顺式-斯蒂苯二酚在固态下发出具有高量子产率的荧光，并表现出聚集诱导的发射增强。炔基硼化反应的广泛底物范围提供了对电子多样化结构的便捷访问，从而可以微调光吸收/发射特性。具有二苯基氨基的含硼的π-延伸的顺式-sti通过分子内的电荷转移跃迁显示出溶剂化荧光变色。
• Pyrazole-Based Lactate Dehydrogenase Inhibitors with Optimized Cell Activity and Pharmacokinetic Properties
  作者：Ganesha Rai、Daniel J. Urban、Bryan T. Mott、Xin Hu、Shyh-Ming Yang、Gloria A. Benavides、Michelle S. Johnson、Giuseppe L. Squadrito、Kyle R. Brimacombe、Tobie D. Lee、Dorian M. Cheff、Hu Zhu、Mark J. Henderson、Katherine Pohida、Gary A. Sulikowski、David M. Dranow、Md Kabir、Pranav Shah、Elias Padilha、Dingyin Tao、Yuhong Fang、Plamen P. Christov、Kwangho Kim、Somnath Jana、Pavan Muttil、Tamara Anderson、Nitesh K. Kunda、Helen J. Hathaway、Donna F. Kusewitt、Nobu Oshima、Murali Cherukuri、Douglas R. Davies、Jeffrey P. Norenberg、Larry A. Sklar、William J. Moore、Chi V. Dang、Gordon M. Stott、Leonard Neckers、Andrew J. Flint、Victor M. Darley-Usmar、Anton Simeonov、Alex G. Waterson、Ajit Jadhav、Matthew D. Hall、David J. Maloney

  DOI：10.1021/acs.jmedchem.0c00916

  日期：2020.10.8

  of compounds, using structure-based design concepts, coupled with optimization of cellular potency, in vitro drug–target residence times, and in vivo PK properties, to identify first-in-class inhibitors that demonstrate LDH inhibition in vivo. The lead compounds, named NCATS-SM1440 (43) and NCATS-SM1441 (52), possess desirable attributes for further studying the effect of in vivo LDH inhibition.

  乳酸脱氢酶（LDH）催化丙酮酸向乳酸的转化，同时还原的烟酰胺腺嘌呤二核苷酸的氧化是糖酵解途径的最后一步。糖酵解在癌细胞的代谢可塑性中起重要作用，长期以来一直被认为是潜在的治疗靶点。因此，LDH的有效的选择性抑制剂代表了一种有吸引力的治疗方法。然而，迄今为止，药理剂未能实现体内显着的靶标结合，可能是因为蛋白质以非常高的浓度存在于细胞中。我们在此报告了一项领先的优化运动，该研究使用基于结构的设计概念，重点研究了吡唑基系列化合物，并在体外优化了细胞效能药物-靶标的停留时间和体内PK特性，以鉴定可证明LDH在体内具有抑制作用的一流抑制剂。名为NCATS-SM1440（43）和NCATS-SM1441（52）的先导化合物具有进一步研究体内LDH抑制作用所需的属性。
• Cobalt(I)-Mediated Preparation of Polyborylated Cyclohexadienes: Scope, Limitations, and Mechanistic Insight
  作者：Anaïs Geny、David Lebœuf、Gabriel Rouquié、K. Peter C. Vollhardt、Max Malacria、Vincent Gandon、Corinne Aubert

  DOI：10.1002/chem.200700337

  日期：2007.6.25

  proper choice of substituents allowed the preparation of 1,3-diborylated cyclohexadienes in a highly selective manner. Alternatively, 1,4-diborylated cyclohexadienes could be prepared from diborylated diynes. The scope of this reaction has been examined and found to include electron-poor, electron-rich, linear, and cyclic alkenes. The diborylated cyclohexadienes were submitted to single or double Suzuki-Miyaura

  通过分子间CoCp介导的炔基硼酸松果酸酯与烯烃的分子间CoCp介导的[2 + 2 + 2]共环化，然后用铁进行氧化脱金属，制备了一系列1,3-和1,4-二硼基-1,3-环己二烯）氯化物。已经研究了在硼化炔烃上的取代对化学和区域选择性的影响，表明了空间控制。取代基的适当选择允许以高度选择性的方式的1,3-环己二烯diborylated制备。备选地，可以由二硼化的二炔制备1，4-二硼化的环己二烯。已经检查了该反应的范围，发现该反应的范围包括贫电子，富电子，直链和环状烯烃。将二硼化的环己二烯与卤代芳烃进行单或双Suzuki-Miyaura交叉偶联反应，得到聚芳基化体系。
• Copper-Silver Dual Catalyzed Decyanative C-Se Cross-Coupling
  作者：Nirmalya Mukherjee、Debasish Kundu、Brindaban C. Ranu

  DOI：10.1002/adsc.201600933

  日期：2017.1.19

  develop a decyanative cross‐coupling through metal‐assisted nucleophilic displacement, which is less explored so far. Thus, a decyanative cross‐coupling of aryl selenocyanate with aryl‐/alkylacetylenes, boronic acids and silanes has been accomplished by a copper‐assisted nucleophilic displacement reaction for an easy access to a series of diaryl, aryl alkyl, aryl vinyl and aryl alkynyl selenides. The best

  传统上，金属催化的交叉偶联反应受不同亲核试剂取代卤素，甲苯磺酸盐等离去基团的控制，从而导致碳-碳和碳-杂原子键的形成。除了传统的离去基团在偶联反应中的取代，脱氰交叉偶联也受到了当前的关注。这项工作的目的是通过金属辅助的亲核置换来发展脱氰交叉偶联，到目前为止，这一研究还很少。因此，通过铜辅助的亲核取代反应可以轻松实现一系列二芳基，芳基烷基，芳基乙烯基和芳基炔基硒化物的芳基硒酸芳基酯与芳基/烷基乙炔，硼酸和硅烷的脱氰交叉偶联。 。2，Ag 2 CO 3（20 mol％）和Cs 2 CO 3（1当量）在N-甲基吡咯烷酮（NMP）中于100°C放置8 h 。操作简单，产率高和通用性强的优点使该方法更具吸引力。已经提出了一种机械途径。银在脱氰过程中起关键作用。基于UV，EPR，HRMS和IR分析数据以及对照实验的结果，提出了这种脱氰碳-硒交叉偶联的可能机理。
• Synthesis of β,β-Disubstituted Vinyl Boronates via the Ruthenium-Catalyzed Alder Ene Reaction of Borylated Alkynes and Alkenes
  作者：Eric C. Hansen、Daesung Lee

  DOI：10.1021/ja0424629

  日期：2005.3.1

  Ruthenium-catalyzed Alder ene reactions between borylated alkynes and terminal alkenes give the corresponding β,β-disubstituted vinyl boronates with high selectivity for the branched isomer. The stereochemistry of the vinyl boronate moiety was the result of a formal trans addition of the ene subunit across the alkyne, which is the opposite stereochemical outcome observed for other internal alkynes

  硼化炔烃和末端烯烃之间的钌催化阿尔德烯反应产生相应的 β,β-二取代乙烯基硼酸酯，对支化异构体具有高选择性。乙烯基硼酸酯部分的立体化学是烯亚基在炔烃上正式反式加成的结果，这与其他内部炔烃观察到的立体化学结果相反。