(1S,2S,3R,5S)-2α,3α-pinanediol methylboronic ester | 84110-38-3

• 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: (1S,2S,3R,5S)-2α,3α-pinanediol methylboronic ester
• 英文别名: (+)-pinanediol methaneboronate；(+)-pinanediol methylboronate；(s)-pinanediol methylboronate；(1S,2S,6R,8S)-2,4,9,9-tetramethyl-3,5-dioxa-4-boratricyclo[6.1.1.02,6]decane
• CAS: 84110-38-3
• 化学式: C₁₁H₁₉BO₂
• 分子量: 194.082
• InChiKey: HDEAXDWSHFKERM-CKEKPRIKSA-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：

  (1S,2S,3R,5S)-2α,3α-pinanediol methylboronic ester 在 盐酸 、 正丁基锂 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 正己烷 为溶剂， 反应 3.5h， 生成 (alphaR,3aS,4S,6S,7aR)-六氢-alpha,3a,8,8-四甲基-4,6-甲桥-1,3,2-苯并二氧硼烷-2-甲胺盐酸盐 (1:1)
  参考文献：
  名称：

  [EN] BETA-LACTAMASE INHIBITORS
  [FR] INHIBITEURS DE BÊTA-LACTAMASE

  摘要：

  本公开涉及含硼化合物和治疗与抗生素耐药微生物相关感染的方法。

  公开号：

  WO2013056163A1
• 作为产物：
  描述：

  (+)-α-蒎烯 在 吡啶 、 四氧化锇 、 magnesium sulfate 、 N-甲基吗啉氧化物 作用下， 以 乙醚 、 水 、 叔丁醇 为溶剂， 生成 (1S,2S,3R,5S)-2α,3α-pinanediol methylboronic ester
  参考文献：
  名称：

  Expanding the scope of PNA-encoded libraries: divergent synthesis of libraries targeting cysteine, serine and metallo-proteases as well as tyrosine phosphatases

  摘要：

  Seven PNA-encoded combinatorial libraries targeting proteases and phosphatases with covalent reversible and irreversible mechanism-based inhibitors were prepared. The libraries were synthesized using modified PNA monomers, which dramatically increase the water solubility of the libraries in biologically relevant buffers. The libraries were shown to selectively inhibit targeted enzymes. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.03.033

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
• A Study of Transesterification of Chiral (−)-Pinanediol Methylboronic Ester with Various Structurally Modified Diols
  作者：Chandra D. Roy、Herbert C. Brown

  DOI：10.1007/s00706-007-0681-7

  日期：2007.8

  The transesterification of chiral (−)-pinanediol methylboronic ester was studied with various structurally modified diols by 1H NMR to understand the factors influencing the unusual stability of this boronic ester as well as to find ways of recovering pinanediol from its methylboronic ester. In all the cases, reactions were allowed to proceed to equilibrium. The preliminary experiments indeed have

  通过各种结构改性的二醇，通过1 H NMR研究了手性（-）-with烷二醇甲基硼酸酯的酯交换反应，以了解影响该硼酸酯异常稳定性的因素，并找到从其甲基硼酸酯中回收pin二醇的方法。在所有情况下，使反应进行到平衡。初步实验确实显示了一些令人鼓舞的结果（pin烷二醇的取代率高达40-53％）。在基于环戊烷的 顺式 -1,2-二醇中， 内 -2-苯基 -exo ， exo -2,3-降冰片烷二醇似乎是取代pin烷二醇最有效的二醇（38％）。在基于pin烷的二醇的情况下，使用2-乙基-6,6-二甲基双环[3.1.1]庚烷- 顺式 -2,3-二醇（53％）可获得最佳结果 。有趣的是，观察到与2-苯基-6,6-二甲基双环[3.1.1]庚烷- 顺式 -2,3-二醇的酯交换反应 仅在4天后即可产生50％的转化率，而前一个二醇则需要24天达到平衡。
• Probing the Specificity of the Serine Proteases Subtilisin Carlsberg and α-Chymotrypsin with Enantiomeric 1-Acetamido Boronic Acids. An Unexpected Reversal of the Normal “<scp>l</scp>”-Stereoselectivity Preference
  作者：Valeri Martichonok、J. Bryan Jones

  DOI：10.1021/ja952816j

  日期：1996.1.1

  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.
• Matteson, Donald S.; Ray, Rahul; Rocks, Richard R., Organometallics, 1983, vol. 2, # 11, p. 1536 - 1540
  作者：Matteson, Donald S.、Ray, Rahul、Rocks, Richard R.、Tsai, David J.

  DOI：——

  日期：——
• Tsai, David J. S.; Matteson, Donald S., Organometallics, 1983, vol. 2, # 2, p. 236 - 241
  作者：Tsai, David J. S.、Matteson, Donald S.

  DOI：——

  日期：——