4,4,5,5-tetramethyl-(3-phenylpropyn-2-yl)-1,3,2-dioxaborolane | 1425747-00-7

• 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: 4,4,5,5-tetramethyl-(3-phenylpropyn-2-yl)-1,3,2-dioxaborolane
• 英文别名: 4,4,5,5-tetramethyl-2-(3-phenylprop-2-yn-1-yl)-1,3,2-dioxaborolane；(3-phenyl-2-propynyl)boronic acid pinacol ester；4,4,5,5-Tetramethyl-2-(3-phenylprop-2-ynyl)-1,3,2-dioxaborolane；4,4,5,5-tetramethyl-2-(3-phenylprop-2-ynyl)-1,3,2-dioxaborolane
• CAS: 1425747-00-7
• 化学式: C₁₅H₁₉BO₂
• 分子量: 242.126
• InChiKey: VRDBJJWANFJQCU-UHFFFAOYSA-N

物化性质

• 沸点：
  308.7±25.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.13
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4,4,5,5-tetramethyl-(3-phenylpropyn-2-yl)-1,3,2-dioxaborolane 、 对氯苯乙酮 在 copper(II) isobutyrate 、 lithium tert-butoxide 、 (-)-1,2-双((2R,5R)-2,5-二苯基膦)乙烷 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以97%的产率得到2-(4-chlorophenyl)-3-phenylpenta-3,4-dien-2-ol
  参考文献：
  名称：

  Copper-Catalyst-Controlled Site-Selective Allenylation of Ketones and Aldehydes with Propargyl Boronates

  摘要：

  A practical and highly site-selective copper-PhBPE-catalyst-controlled allenylation with propargyl boronates has been developed. The methodology has shown to be tolerant of diverse ketones and aldehydes providing the allenyl adducts in high selectivity. The BPE ligand and boronate substituents were shown to direct the site selectivity for which either propargyl or allenyl adducts can be acquired in high selectivity. A model is proposed that explains the origin of the site selectivity.

  DOI：

  10.1021/ol400124f
• 作为产物：
  描述：

  碘甲基硼酸频哪醇酯 、 苯乙炔 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 31.0h， 以40%的产率得到4,4,5,5-tetramethyl-(3-phenylpropyn-2-yl)-1,3,2-dioxaborolane
  参考文献：
  名称：

  Diboration of 3-substituted propargylic alcohols using a bimetallic catalyst system: access to (Z)-allyl, vinyldiboronates

  摘要：

  一种Pd/Cu催化剂体系促进了未活化的丙炔醇与五氟硼酸和二硼烷的二硼化反应，生成(Z)-烯丙基、烯基二硼酸酯。

  DOI：

  10.1039/d0cc03563g

文献信息

• An efficient Nozaki–Hiyama allenylation promoted by the acid derived MIL-101 MOF
  作者：Yi Luan、Zonghui Cai、Xiujuan Li、Daniele Ramella、Zongcheng Miao、Wenyu Wang

  DOI：10.1039/c8ra09600g

  日期：——

  catalyst, an efficient Nozaki–Hiyama allenylation reaction was achieved to generate various polyfunctionalized α-allenic alcohols in high yield and good selectivity. Taking advantage of the high acidity of the MIL-101-SO3H MOF structure, such transformations were also achieved under mild reaction conditions and short reaction times. Based on our observed evidence during this study, a mechanism was proposed

  使用市售材料报道了含磺酸的 MIL-101 MOF 催化剂的简明合成。还展示了合成后的 MIL-101-SO 3 H的一系列表征，包括 SEM、XRD、FTIR、BET 和 TGA。使用 MIL-101-SO 3 H 作为催化剂，实现了高效的 Nozaki-Hiyama 烯基化反应，以高收率和良好的选择性生成各种多官能化 α-烯丙醇。利用 MIL-101-SO 3的高酸度H MOF 结构，这种转变也是在温和的反应条件和较短的反应时间下实现的。基于我们在本研究中观察到的证据，提出了一种涉及底物活化/γ-亲核加成反应序列的机制。此外，MIL-101-SO 3 H 催化剂可以在 Nozaki-Hiyama 烯基化反应中循环十次，而不会影响产率和选择性。
• Electrochemical Properties and Reactions of Organoboronic Acid Esters Containing Unsaturated Bonds at Their α-Position
  作者：Kazuhiro Ohtsuka、Shinsuke Inagi、Toshio Fuchigami

  DOI：10.1149/2.0561702jes

  日期：——

  Electrochemical analyses of 2-(cynnamyl) boronic acid pinacol ester and (3-phenyl-2-propynyl) boronic acid pinacol ester, and their trimethylsilyl analogues as well as their parent compounds were comparatively studied by cyclic voltammetry measurements. We found remarkable negative shifts of the oxidation potentials of the organoboronic acid pinacol esters in the presence of fluoride ions compared to those in the absence of fluoride ions. The negative shift observed was more pronounced than that of the corresponding trimethylsilyl compounds. Such marked negative shift seems to be derived from the formation of negatively charged boron-ate complex with fluoride ions as well as beta-effect of organoborate. Anodic acetoxylation of organoboronic acid pinacol esters was achieved in NaOAc/AcOH, while their alkoxylation was successfully carried out in the presence of fluoride ions. (C) 2016 The Electrochemical Society.