p-benzaldehyde dimethyl acetal boronic acid pinacolester | 943239-68-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: p-benzaldehyde dimethyl acetal boronic acid pinacolester
• 英文别名: 2-(4-methoxy-2-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane；4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-benzaldehydedimethyl acetal；2-(4-(dimethoxy methyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane；p-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde dimethylacetal；2-(4-(Dimethoxymethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane；2-[4-(dimethoxymethyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS: 943239-68-7
• 化学式: C₁₅H₂₃BO₄
• 分子量: 278.156
• InChiKey: BAYRKBPKIRVJQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.28
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  p-benzaldehyde dimethyl acetal boronic acid pinacolester 、 2,9-二溴-1,10-菲罗啉 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以40 %的产率得到2-bromo-9-(4-(dimethoxymethyl)phenyl)-1,10-phenanthroline
  参考文献：
  名称：

  鸡丝共价有机框架的分子编织

  摘要：

  分子编织是共价连接线的交织以形成扩展结构。尽管基于 3D 网络的编织已有报道，但 2D 形式仍然很大程度上未被探索。网状化学使用相互拥抱的四面体金属配合物作为交叉点，当连接时，通常会形成 3D 编织结构。实现二维编织图案需要具有整体平面几何形状的交叉点。我们表明，由多个金属络合物单元组成的多核螺旋，因此具有多个转角，非常适合这方面。通过网状螺旋单元，我们成功地获得了基于熟悉的鸡丝图案的二维编织结构。

  DOI：

  10.1016/j.chempr.2023.07.015
• 作为产物：
  描述：

  频那醇硼烷 在 magnesium 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 6.5h， 生成 p-benzaldehyde dimethyl acetal boronic acid pinacolester
  参考文献：
  名称：

  Preparation and reactions of 4-iodobutyl pinacolborate. Synthesis of substituted alkyl and aryl pinacolboronates via 4-iodobutyl pinacolborate utilizing tetrahydrofuran as the leaving group

  摘要：

  Iodine reacts with 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (HBpin), under ambient reaction conditions in THF, to form the iodoalkylborate species 2-(4-iodobutoxy)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (4-IboxBpin). Apparently, one-half equivalent of 12 reacts with HBpin to form IBpin in pentanes, which in turn cleaves THF to form the 4-IboxBpin. Alkyl and aryl Grignard reagents, prepared under Barbier conditions, then react with 4-IboxBpin to form the corresponding alkyl and aryl pinacolboronates while reforming and liberating THF as the leaving group. Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2014.12.033

文献信息

• Copper‐Catalyzed Monoorganylation of Trialkyl Borates with Functionalized Organozinc Pivalates
  作者：Ying Fu、Bei‐Lei Gou、Chun‐Zhao Shi、Zhengyin Du、Tong Shen

  DOI：10.1002/cctc.201800939

  日期：2018.10.9

  Organozinc pivalates, a recently developed air‐ and moisture‐stable organozinc species, were found for the first time as excellent organometallic species in the monoorganylation of trialkyl borates whereby boronic acids were prepared in high yields. The significant advantage of organozinc pivalates over another previously employed organometallic reagents, e. g., organolithium reagents, Grignard reagents

  新出现的有机锌新戊酸酯是一种对空气和水分稳定的有机锌物种，在硼酸三烷基酯的单有机基化中首次被发现是极好的有机金属物种，从而可以高产率制备硼酸。有机锌新戊酸酯相对于另一种先前使用的有机金属试剂的显着优势。例如，有机锂试剂，格氏试剂和卤化有机锌是完全抑制了多有机基化副产物如硼酸和三烷基硼烷的产生。此外，原位生成的硼酸盐可直接安排到Suzuki-Miyaura型交叉偶联反应中，从而以高收率生产联芳基。
• Preparation of acetals from aldehydes and alcohols under basic conditions
  作者：Jakub Grabowski、Jarosław M. Granda、Janusz Jurczak

  DOI：10.1039/c8ob00017d

  日期：——

  A new, simple protocol for the synthesis of acetals under basic conditions from non-enolizable aldehydes and alcohols has been reported. Such reactivity is facilitated by a sodium alkoxide along with a corresponding trifluoroacetate ester, utilizing formation of sodium trifluoroacetate as a driving force for acetal formation. The usefulness of this protocol is demonstrated by its orthogonality with

  已经报道了在碱性条件下由不可烯化的醛和醇合成乙缩醛的一种新的，简单的方案。醇钠与相应的三氟乙酸酯一起促进了这种反应，利用三氟乙酸钠的形成作为缩醛形成的驱动力。通过与各种酸敏感保护基团的正交性以及与官能团的良好相容性，证明该方案的实用性，在酸性条件下由醛类和醇类合成时，可提供合成有用的乙缩醛以补充合成。
• Hydride as a Leaving Group in the Reaction of Pinacolborane with Halides under Ambient Grignard and Barbier Conditions. One-Pot Synthesis of Alkyl, Aryl, Heteroaryl, Vinyl, and Allyl Pinacolboronic Esters
  作者：Jacob W. Clary、Terry J. Rettenmaier、Rachel Snelling、Whitney Bryks、Jesse Banwell、W. Todd Wipke、Bakthan Singaram

  DOI：10.1021/jo201093u

  日期：2011.12.2

  addition of pentane to the reaction mixture. DFT calculations (Gaussian09) at the B3LYP/6-31G(d) level of theory show that disproportionation of HMgBr to MgH2 and MgBr2 is viable in the coordinating ethereal solvents. This reaction also can be carried out under Barbier conditions, where the neat PinBH is added to the flask prior to the in situ formation of Grignard reagent from the corresponding organic

  格氏试剂（脂族，芳族，杂芳族，乙烯基或烯丙基）与1当量的4,4,5,5-四甲基-1,3,2-二氧杂硼烷（pinacolborane，PinBH）在环境温度下在四氢呋喃（THF）中反应为提供相应的频哪醇硼酸酯。最初形成的二烷氧基烷基硼氢化物中间体可快速消除溴化氢化镁（HMgBr），并以非常好的收率提供硼酸酯产品。在将戊烷加入到反应混合物中之后，溴化氢溴化铵（HMgBr）歧化为氢化镁（MgH 2）和溴化镁（MgBr 2）的1：1混合物。在B3LYP / 6-31G（d）理论水平上的DFT计算（Gaussian09）显示，HMgBr歧化为MgH 2和MgBr 2在配位醚溶剂中是可行的。该反应也可以在Barbier条件下进行，其中在从相应的有机卤化物和镁金属原位形成格氏试剂之前，将纯净的PinBH加入到烧瓶中。在Barbier条件下合成萘酚硼酸酯不能从反应性卤化物（例如苄基和烯丙基卤化物）中产生W
• Palladium-Catalyzed <i>ipso</i>-Borylation of Aryl Sulfides with Diborons
  作者：M. Bhanuchandra、Alexandre Baralle、Shinya Otsuka、Keisuke Nogi、Hideki Yorimitsu、Atsuhiro Osuka

  DOI：10.1021/acs.orglett.6b01305

  日期：2016.6.17

  ipso-borylation of aryl sulfides with diboron reagents has been achieved, providing arylboronate esters of synthetic use. The key conditions to transform inherently reluctant C–S bonds into C–B bonds include a palladium-NHC (N-heterocyclic carbene) precatalyst, bis(pinacolato)diboron, and lithium hexamethyldisilazide. This protocol is applicable to a reasonable range of aryl alkyl sulfides. Twofold borylation

  一种催化宫浦型本位与二硼试剂芳基硫化物的-borylation已经实现，从而提供合成的使用arylboronate酯。将本来就不愿意的C–S键转换为C–B键的关键条件包括钯-NHC（N-杂环卡宾）预催化剂，双（频哪醇）二硼和六甲基二硅叠氮化锂。该协议适用于合理范围的芳基烷基硫化物。在二苯硫醚的反应中观察到双重硼化。
• Preparation and reactions of 4-iodobutyl pinacolborate. Synthesis of substituted alkyl and aryl pinacolboronates via 4-iodobutyl pinacolborate utilizing tetrahydrofuran as the leaving group
  作者：Chris L. Murphy、Aaron Hall、Emily J. Roberts、Matthew D. Ryan、Jacob W. Clary、Bakthan Singaram

  DOI：10.1016/j.tetlet.2014.12.033

  日期：2015.6

  Iodine reacts with 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (HBpin), under ambient reaction conditions in THF, to form the iodoalkylborate species 2-(4-iodobutoxy)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (4-IboxBpin). Apparently, one-half equivalent of 12 reacts with HBpin to form IBpin in pentanes, which in turn cleaves THF to form the 4-IboxBpin. Alkyl and aryl Grignard reagents, prepared under Barbier conditions, then react with 4-IboxBpin to form the corresponding alkyl and aryl pinacolboronates while reforming and liberating THF as the leaving group. Published by Elsevier Ltd.