2-(2-chlorophenyl)-1,3,2-dioxaborolane | 871817-14-0

• 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: 2-(2-chlorophenyl)-1,3,2-dioxaborolane
• 英文别名: 2-(2-Chlorophenyl)-1,3,2-dioxaborolane
• CAS: 871817-14-0
• 化学式: C₈H₈BClO₂
• 分子量: 182.414
• InChiKey: RNZFOSSIYCRAAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.08
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-chlorophenyl)-1,3,2-dioxaborolane 以 四氢呋喃 、 乙醇 为溶剂， 生成 (2-Chlorophenyl)vinylborinic acid 8-hydroxyquinoline ester
  参考文献：
  名称：

  Identification of Borinic Esters as Inhibitors of Bacterial Cell Growth and Bacterial Methyltransferases, CcrM and MenH

  摘要：

  As bacteria continue to develop resistance toward current antibiotics, we find ourselves in a continual battle to identify new antibacterial agents and targets. We report herein a class of boron-containing compounds termed borinic esters that have broad spectrum antibacterial activity with minimum inhibitory concentrations (MIC) in the low microgram/mL range. These compounds were identified by screening for inhibitors against Caulobacter crescentus CcrM, an essential DNA methyltransferase from Gram negative alpha-proteobacteria. In addition, we demonstrate that borinic esters inhibit menaquinone methyltransferase in Gram positive bacteria using a new biochemical assay for MenH from Bacillus subtilis. Our data demonstrate the potential for further development of borinic esters as antibacterial agents as well as leads to explore more specific inhibitors against two essential bacterial enzymes.

  DOI：

  10.1021/jm050676a
• 作为产物：
  描述：

  2-氯苯基硼酸 、 乙二醇 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 2-(2-chlorophenyl)-1,3,2-dioxaborolane
  参考文献：
  名称：

  铜催化的见解：铃木-宫浦的芳基/吲哚基硼酸酯交叉偶联中原位形成的纳米Cu 2 O

  摘要：

  已经研究了无配体铜催化3,5-二碘吡啶与芳基和吲哚硼酸酯的Suzuki-Miyaura偶联，收率良好。原位生成的纳米铜的2从氯化亚铜ø 2在反应条件下已经发现首次。通过5-碘嘧啶，碘吡啶，碘苯和二碘苯的芳基化进一步证明了反应的一般性，并产生了良好至中等的收率。此外，双吲哚生物碱Scalaridine A已成功地以60％的总收率合成。

  DOI：

  10.1021/acs.orglett.7b01669

文献信息

• One-Pot Synthesis of Chiral Dihydrobenzofuran Framework via Rh/Pd Catalysis
  作者：Gavin Chit Tsui、Jennifer Tsoung、Patrick Dougan、Mark Lautens

  DOI：10.1021/ol302646a

  日期：2012.11.2

  A one-pot synthesis of the chiral dihydrobenzofuran framework is described. The method utilizes Rh-catalyzed asymmetric ring opening (ARO) and Pd-catalyzed C–O coupling to furnish the product in excellent enantioselectivity without isolation of intermediates. Systematic metal–ligand studies were carried out to investigate the compatibility of each catalytic system using product enantiopurity as an

  描述了手性二氢苯并呋喃骨架的一锅合成。该方法利用Rh催化的不对称开环（ARO）和Pd催化的C–O偶联，以优异的对映选择性提供了产品，而无需分离中间体。进行了系统的金属-配体研究，以产物对映体纯度为指标，研究了每个催化体系的相容性。
• Insight into Copper Catalysis: In Situ Formed Nano Cu₂O in Suzuki–Miyaura Cross-Coupling of Aryl/Indolyl Boronates
  作者：Ganapathy Ranjani、Rajagopal Nagarajan

  DOI：10.1021/acs.orglett.7b01669

  日期：2017.8.4

  aryl and indole boronates has been explored in good to excellent yields. In situ generation of nano-Cu2O from CuCl2 under the reaction conditions has been discovered for the first time. The generality of the reaction was further demonstrated by the arylation of 5-iodopyrimidine, iodopyridines, iodobenzenes, and diiodobenzenes and resulted in good to moderate yields. Moreover, bisindole alkaloid Scalaridine

  已经研究了无配体铜催化3,5-二碘吡啶与芳基和吲哚硼酸酯的Suzuki-Miyaura偶联，收率良好。原位生成的纳米铜的2从氯化亚铜ø 2在反应条件下已经发现首次。通过5-碘嘧啶，碘吡啶，碘苯和二碘苯的芳基化进一步证明了反应的一般性，并产生了良好至中等的收率。此外，双吲哚生物碱Scalaridine A已成功地以60％的总收率合成。
• Identification of Borinic Esters as Inhibitors of Bacterial Cell Growth and Bacterial Methyltransferases, CcrM and MenH
  作者：Stephen J. Benkovic、Stephen J. Baker、M. R. K. Alley、Youn-Hi Woo、Yong-Kang Zhang、Tsutomu Akama、Weimin Mao、Justin Baboval、P. T. Ravi Rajagopalan、Mark Wall、Lyn Sue Kahng、Ali Tavassoli、Lucy Shapiro

  DOI：10.1021/jm050676a

  日期：2005.11.1

  As bacteria continue to develop resistance toward current antibiotics, we find ourselves in a continual battle to identify new antibacterial agents and targets. We report herein a class of boron-containing compounds termed borinic esters that have broad spectrum antibacterial activity with minimum inhibitory concentrations (MIC) in the low microgram/mL range. These compounds were identified by screening for inhibitors against Caulobacter crescentus CcrM, an essential DNA methyltransferase from Gram negative alpha-proteobacteria. In addition, we demonstrate that borinic esters inhibit menaquinone methyltransferase in Gram positive bacteria using a new biochemical assay for MenH from Bacillus subtilis. Our data demonstrate the potential for further development of borinic esters as antibacterial agents as well as leads to explore more specific inhibitors against two essential bacterial enzymes.