(S)-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethanol | 1173922-36-5

• 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: (S)-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethanol
• 英文别名: 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethan-1-ol；(1S)-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethanol
• CAS: 1173922-36-5
• 化学式: C₁₄H₂₁BO₃
• 分子量: 248.13
• InChiKey: XYJVUQXMTOMREX-JTQLQIEISA-N

物化性质

• 沸点：
  357.6±25.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.04
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethanol 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 偶氮二甲酸二异丙酯 、 sodium carbonate 、 三乙胺 、 N,N-二异丙基乙胺 、 三苯基膦 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.67h， 生成 tert-butyl (2-(((4S,7S,10S)-10-((S)-4-((tert-butoxycarbonyl)amino)-2-(2-(4-((S)-1-(tert-butyldisulfanyl)ethyl)phenyl)-4-methylpyrimidine-5-carboxamido)-N-methylbutanamido)-26-(2-((tert-butoxycarbonyl)amino)ethoxy)-4-((cyanomethyl)carbamoyl)-7-methyl-6,9-dioxo-5,8-diaza-1,2(1,3)-dibenzenacyclodecaphane-16-yl)oxy)ethyl)carbamate
  参考文献：
  名称：

  抗多重耐药革兰氏阴性菌的新型 Arylomycin 的设计、合成和生物学评价

  摘要：

  G0775是一种正在临床前研究中评估的arylomycin型SPase I抑制剂，对一些革兰氏阴性菌表现出有效的抗菌活性，但同时也存在抗菌谱窄、药代动力学特性差等缺陷。在此，进行了系统的结构修饰，包括大环骨架、弹头和亲脂区域的优化。优化最终发现了138f ，它对临床分离的碳青霉烯类耐药革兰氏阴性菌，特别是鲍曼不动杆菌和铜绿假单胞菌表现出更有效的活性和更广的谱。 162 （ 138f的游离胺）在大鼠中表现出优异的药代动力学特征。在多重耐药铜绿假单胞菌感染的中性粒细胞减少小鼠大腿模型中， 162的强效体内抗菌功效得到证实，并且优于 G0775（集落形成单位 (CFU) 减少 3.5 个对数 vs 1.1 个对数） ）。这些结果支持162作为进一步研究的潜在抗菌剂。

  DOI：

  10.1021/acs.jmedchem.4c00018
• 作为产物：
  描述：

  频哪醇 以 四氢呋喃 、 aq. phosphate buffer 、 N,N-二甲基甲酰胺 为溶剂， 反应 121.0h， 生成 (S)-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethanol
  参考文献：
  名称：

  Application of a promiscuous Arthrobacter sp. from Antarctic in aerobic (R)-selective deracemization and anaerobic (S)-selective reduction

  摘要：

  Inspired by enzyme-catalyzed reactions with microorganisms found in harsh marine environments, in which the amount of oxygen is restrict, we have shown that Arthrobacter sp. can perform different chemical transformations by switching from anaerobic to aerobic reaction conditions. Depending on the presence or absence of oxygen, either alcohol deracemization or ketone reduction with enantiocomplementary selectivities can be performed by the same microorganism. For example, reactions performed in the presence of oxygen favored the deracemization process, in which a racemic mixture of 1-(4-methylphenyl) ethanol was enriched to the (R)-alcohol in high conversion (94%) and high enantiomeric excess (94%). On the other hand, reaction in the absence of oxygen favored the reduction process, in which 4-methyl-acetophenone was converted to the (S)-alcohol in good conversion (58%) and excellent enantiomeric excess (> 99%). These concepts were applied for both deracemization and enantio selective reduction of heteroatom-containing (silicon, phosphorus, tin and boron) molecules. Moreover, preparative scale reactions were also performed for both chemical processes. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2014.09.016

文献信息

• Lipase-Catalyzed Highly Enantioselective Kinetic Resolution of Boron-Containing Chiral Alcohols
  作者：Leandro H. Andrade、Thiago Barcellos

  DOI：10.1021/ol901091f

  日期：2009.7.16

  to obtain optically pure boron compounds is described. The kinetic resolution of boron-containing chiral alcohols via enantioselective transesterification catalyzed by lipases was studied. Aromatic, allylic, and aliphatic secondary alcohols containing a boronate ester or boronic acid group were resolved by lipase from Candida antartica (CALB), and excellent E values (E > 200) and high enantiomeric excesses

  描述了酶作为催化剂首次获得光学纯硼化合物的应用。研究了含硼手性醇通过脂肪酶催化的对映选择性酯交换反应的动力学拆分。含有硼酸酯或硼酸基团的芳族，烯丙基和脂族仲醇可通过南极假丝酵母（CALB）的脂肪酶分解，并具有出色的E值（E > 200）和高对映体过量（最高> 99％）获得底物和乙酰化产物。
• Stereocomplementary asymmetric bioreduction of boron-containing ketones mediated by alcohol dehydrogenases
  作者：Thiago Barcellos、Katharina Tauber、Wolfgang Kroutil、Leandro H. Andrade

  DOI：10.1016/j.tetasy.2011.10.012

  日期：2011.10

  Optically active boron-containing alcohols were prepared via the stereoselective reduction of the corresponding carbonyl compounds by alcohol dehydrogenases. Depending on the substrate, both (R)-alcohols and (S)-alcohols were obtained with excellent enantioselectivity (up to >99% ee) employing either ADH-A or LB-ADH. (C) 2011 Elsevier Ltd. All rights reserved.
• Application of a promiscuous Arthrobacter sp. from Antarctic in aerobic (R)-selective deracemization and anaerobic (S)-selective reduction
  作者：Dayvson J. Palmeira、Lidiane S. Araújo、Juliana C. Abreu、Leandro H. Andrade

  DOI：10.1016/j.molcatb.2014.09.016

  日期：2014.12

  Inspired by enzyme-catalyzed reactions with microorganisms found in harsh marine environments, in which the amount of oxygen is restrict, we have shown that Arthrobacter sp. can perform different chemical transformations by switching from anaerobic to aerobic reaction conditions. Depending on the presence or absence of oxygen, either alcohol deracemization or ketone reduction with enantiocomplementary selectivities can be performed by the same microorganism. For example, reactions performed in the presence of oxygen favored the deracemization process, in which a racemic mixture of 1-(4-methylphenyl) ethanol was enriched to the (R)-alcohol in high conversion (94%) and high enantiomeric excess (94%). On the other hand, reaction in the absence of oxygen favored the reduction process, in which 4-methyl-acetophenone was converted to the (S)-alcohol in good conversion (58%) and excellent enantiomeric excess (> 99%). These concepts were applied for both deracemization and enantio selective reduction of heteroatom-containing (silicon, phosphorus, tin and boron) molecules. Moreover, preparative scale reactions were also performed for both chemical processes. (C) 2014 Elsevier B.V. All rights reserved.
• Design, Synthesis, and Biological Evaluation of Novel Arylomycins against Multidrug-Resistant Gram-Negative Bacteria
  作者：Yinyong Zhang、Dan Zhang、Wenhao Zhao、Hongyuan Li、Zhengyu Lu、Bin Guo、Xin Meng、Xianli Zhou、Yushe Yang

  DOI：10.1021/acs.jmedchem.4c00018

  日期：2024.4.25

  showed more potent activity and a broader spectrum against clinically isolated carbapenem-resistant Gram-negative bacteria, especially against Acinetobacter baumannii and Pseudomonas aeruginosa. 162, the free amine of 138f, exhibited an excellent pharmacokinetic profile in rats. In a neutropenic mouse thigh model of infection with multidrug-resistant P. aeruginosa, the potent in vivo antibacterial efficacy

  G0775是一种正在临床前研究中评估的arylomycin型SPase I抑制剂，对一些革兰氏阴性菌表现出有效的抗菌活性，但同时也存在抗菌谱窄、药代动力学特性差等缺陷。在此，进行了系统的结构修饰，包括大环骨架、弹头和亲脂区域的优化。优化最终发现了138f ，它对临床分离的碳青霉烯类耐药革兰氏阴性菌，特别是鲍曼不动杆菌和铜绿假单胞菌表现出更有效的活性和更广的谱。 162 （ 138f的游离胺）在大鼠中表现出优异的药代动力学特征。在多重耐药铜绿假单胞菌感染的中性粒细胞减少小鼠大腿模型中， 162的强效体内抗菌功效得到证实，并且优于 G0775（集落形成单位 (CFU) 减少 3.5 个对数 vs 1.1 个对数） ）。这些结果支持162作为进一步研究的潜在抗菌剂。