(r)-pinanediol methylboronate | 99881-74-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (r)-pinanediol methylboronate
• 英文别名: (-)-pinanediol methylboronate；(1R,2R,6S,8R)-2,4,9,9-tetramethyl-3,5-dioxa-4-boratricyclo[6.1.1.02,6]decane
• CAS: 99881-74-0
• 化学式: C₁₁H₁₉BO₂
• 分子量: 194.082
• InChiKey: HDEAXDWSHFKERM-SDNRWEOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.34
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  (r)-pinanediol methylboronate 以 四氢呋喃 为溶剂， 反应 3.75h， 生成
  参考文献：
  名称：

  Homoallylboration and Homocrotylboration of Aldehydes

  摘要：

  A simple method for addition of homoallylic fragments to aldehydes is described. Cydopropanated allylboration reagents react with aldehydes in the presence of PhBCl2 to give high yields of bishomoallyl alcohols. Cyclopropanated cis- and trans-crotyl reagents afford the corresponding 1,3-anti- and 1,3-syn-methyl-substituted "homocrotylated" alcohols with high selectivity, consistent with a Zimmerman-Traxler transition state. Accordingly, the optically active alpha-substituted reactant affords the E-substituted product in 97:3 er.

  DOI：

  10.1021/ja2048682
• 作为产物：
  描述：

  硼酸三甲酯 、 (1R,2R,3S,5R)-(-)-2,3-蒎烷二醇 、 甲基溴化镁 以 乙醚 为溶剂， 以41%的产率得到(r)-pinanediol methylboronate
  参考文献：
  名称：

  Probing the Specificity of the Serine Proteases Subtilisin Carlsberg and α-Chymotrypsin with Enantiomeric 1-Acetamido Boronic Acids. An Unexpected Reversal of the Normal “l”-Stereoselectivity Preference

  摘要：

  Enantiomeric 1-acetamido boronic acids, which are N-acetyl transition state analog inhibitor analogs of L- and D-forms of the amino acids alanine, phenylalanine, p-fluorophenylalanine, p-chlorophenylalanine, and 1-naphthylalanine, have been evaluated as inhibitors of the serine proteases subtilisin Carlsberg (SC) and alpha-chymotrypsin (CT). All of the boronic acids are powerful competitive inhibitors of both enzymes, with, as expected, the L-enantiomers being generally more potent than the D-enantiomers. However, a dramatic reversal of the normal stereoselectivity preference was observed in the inhibition of CT by [1-acetamido-2-(1-naphthyl)ethyl]boronic acid, with the D-enantiomer becoming a 25-fold more potent inhibitor than the L-enantiomer. Furthermore, the K-I of 127 nM for CT inhibition by this D-enantiomer is the lowest of any of the boronic acids evaluated. Molecular modeling analyses of the possible binding modes of the inhibitors suggest that the stereoselectivity reversal is due to S-1-pocket orientations of naphthyl groups that are different from those of the aromatic side chains of the phenylalanine analogs.

  DOI：

  10.1021/ja952816j

文献信息

• 99% Chirally selective synthesis via pinanediol boronic esters: insect pheromones, diols, and an amino alcohol
  作者：Donald S. Matteson、Kizhakethil Mathew. Sadhu、Mark L. Peterson

  DOI：10.1021/ja00264a039

  日期：1986.2

  Synthese en particulier du methyl-4 heptanol-3, brevicomine, eldanolide, decanediol-5,6, methyl-6 undecanediol-5,7 et amino-6 decanol-5

  合成这些特别是甲基-4 庚醇-3、短苯胺、eldanolide、癸二醇-5,6、甲基-6 十一烷二醇-5,7 和氨基-6 癸醇-5
• Sulfonamidoboronic Acids as “Cross-Class” Inhibitors of an Expanded-Spectrum Class C Cephalosporinase, ADC-33, and a Class D Carbapenemase, OXA-24/40: Strategic Compound Design to Combat Resistance in Acinetobacter baumannii
  作者：Maria Luisa Introvigne、Trevor J. Beardsley、Micah C. Fernando、David A. Leonard、Bradley J. Wallar、Susan D. Rudin、Magdalena A. Taracila、Philip N. Rather、Jennifer M. Colquhoun、Shaina Song、Francesco Fini、Kristine M. Hujer、Andrea M. Hujer、Fabio Prati、Rachel A. Powers、Robert A. Bonomo、Emilia Caselli

  DOI：10.3390/antibiotics12040644

  日期：——

  capable of hydrolyzing β-lactam antibiotics. Co-expression of multiple classes of β-lactamases is present in CRAB; therefore, the design and synthesis of “cross-class” inhibitors is an important strategy to preserve the efficacy of currently available antibiotics. To identify new, nonclassical β-lactamase inhibitors, we previously identified a sulfonamidomethaneboronic acid CR167 active against Acinetobacter-derived

  鲍曼不动杆菌是一种革兰氏阴性菌，被世界卫生组织 (WHO) 列为紧急威胁病原体。由于对 β-内酰胺的耐药机制复杂，耐碳青霉烯类鲍曼不动杆菌 (CRAB) 尤其面临治疗挑战。最重要的机制之一是产生能够水解 β-内酰胺抗生素的 β-内酰胺酶。CRAB 中存在多种 β-内酰胺酶的共表达；因此，设计和合成“跨类”抑制剂是保持现有抗生素疗效的重要策略。为了鉴定新的非经典 β-内酰胺酶抑制剂，我们之前鉴定了一种磺胺甲烷硼酸 CR167，它对不动杆菌衍生的 C 类 β-内酰胺酶 (ADC-7) 具有活性。该化合物对 ADC-7 具有亲和力，Ki = 160 nM，并证明能够降低不同细菌菌株中头孢他啶和头孢噻肟的 MIC 值。在此，我们描述了 CR167 对鲍曼不动杆菌中其他 β-内酰胺酶的活性：头孢吡肟水解 C 类超广谱 β-内酰胺酶 (ESAC) ADC-33 和碳青霉烯类水解 OXA-24/40（D