(+)-(3-溴丙基)硼酸蒎烷二醇酯 | 90084-37-0

• 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
• 中文名称: (+)-(3-溴丙基)硼酸蒎烷二醇酯
• 英文名称: (3aS,4S,6S,7aR)-2-(3-bromopropyl)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole
• 英文别名: (+)-pinanediol 3-bromopropaneboronate；[1S-(1α,2β,3β,5α)]-2,6,6-trimethylbicyclo[3.1.1]heptane-2,3-diol (3-bromopropyl)boronate；(S)-pinanediol (3-bromopropyl)boronate；(+)-(3-Bromopropyl)boronic Acid Pinanediol Ester；(1S,2S,6R,8S)-4-(3-bromopropyl)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.02,6]decane
• CAS: 90084-37-0
• 化学式: C₁₃H₂₂BBrO₂
• 分子量: 301.031
• InChiKey: IFWLNKNUIWTYGB-KQXIARHKSA-N

物化性质

• 沸点：
  313.7±25.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  3
• 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：

  (+)-(3-溴丙基)硼酸蒎烷二醇酯 在 正丁基锂 、 sodium azide 、 N,N-二异丙基乙胺 、 potassium iodide 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.33h， 生成
  参考文献：
  名称：

  [EN] BORONIC ACID DERIVATIVES AND USES THEREOF
  [FR] DÉRIVÉS D'ACIDE BORONIQUE ET LEURS UTILISATIONS

  摘要：

  这项发明涉及一种新型的化学式I的硼酸衍生物，以及在预防（例如，延缓或减少发展风险）和治疗（例如，控制、缓解或减缓进展）老年性黄斑变性（AMD）及眼部相关疾病中有用的药用盐、溶剂化合物、盐的溶剂化合物和其前体。这些疾病包括干性AMD、湿性AMD、地理性萎缩、糖尿病视网膜病变、早产儿视网膜病变、多发性脉络膜血管病变以及视网膜或光感受细胞的退化。本公开的发明还涉及预防、减缓进展和治疗干性AMD、湿性AMD和地理性萎缩、糖尿病视网膜病变、早产儿视网膜病变、多发性脉络膜血管病变以及视网膜或光感受细胞的方法，包括：给予所述发明化合物的治疗有效量。本发明的化合物是HTRA1的抑制剂。因此，本发明的化合物在预防和治疗一系列（全部或部分）由HTRA1介导的疾病中有用。本发明的化合物还可用于抑制眼部或关节炎或相关疾病部位中的HTRA1蛋白酶活性。

  公开号：

  WO2016100555A1
• 作为产物：
  描述：

  (+)-α-蒎烯 在 吡啶 、 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 水 、 叔丁醇 为溶剂， 反应 4.0h， 生成 (+)-(3-溴丙基)硼酸蒎烷二醇酯
  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

• Peptide–Boronic Acid Inhibitors of Flaviviral Proteases: Medicinal Chemistry and Structural Biology
  作者：Christoph Nitsche、Linlin Zhang、Lena F. Weigel、Jonas Schilz、Dominik Graf、Ralf Bartenschlager、Rolf Hilgenfeld、Christian D. Klein

  DOI：10.1021/acs.jmedchem.6b01021

  日期：2017.1.12

  A thousand-fold affinity gain is achieved by introduction of a C-terminal boronic acid moiety into dipeptidic inhibitors of the Zika, West Nile, and dengue virus proteases. The resulting compounds have Ki values in the two-digit nanomolar range, are not cytotoxic, and inhibit virus replication. Structure–activity relationships and a high resolution X-ray cocrystal structure with West Nile virus protease

  通过将C末端硼酸部分引入Zika，West Nile和登革热病毒蛋白酶的二肽抑制剂中，可以实现千倍的亲和力提高。所得化合物的K i值在两位数纳摩尔范围内，无细胞毒性，并抑制病毒复制。与西尼罗河病毒蛋白酶的结构活性关系和高分辨率X射线共晶体结构为针对新兴黄病毒病原体的优化共价可逆抑制剂的设计提供了基础。
• Asymmetric Alkyldifluoroboranes and Their Use in Secondary Amine Synthesis
  作者：Donald S. Matteson、Gyung Youn Kim

  DOI：10.1021/ol025973d

  日期：2002.6.1

  [reaction: see text] Asymmetric diol boronic esters with potassium bifluoride form the corresponding alkyltrifluoroborate and free diol under mild conditions. Defluoridation with tetrachlorosilane produces an alkyldifluoroborane intermediate. This conversion of relatively unreactive boronic esters to derivatives that are strong Lewis acids opens new synthetic opportunities, as illustrated by the preparation

  [反应：见正文]不对称二醇硼酸酯与氟化氢钾在温和条件下形成相应的烷基三氟硼酸酯和游离二醇。用四氯硅烷脱氟产生烷基二氟硼烷中间体。相对不活泼的硼酸酯向强路易斯酸衍生物的这种转化打开了新的合成机会，如由a烷二醇或1,2-二环己基-1,2-酯制备（R）-2-苯基吡咯烷在98％ee中的制备说明。 （2-苯基-4-叠氮丁基）三氟硼酸钾形成乙二醇硼酸酯。
• Matteson, Donald S.; Jesthi, Pradipta K.; Sadhu, Kizhakethil M., Organometallics, 1984, vol. 3, # 8, p. 1284 - 1288
  作者：Matteson, Donald S.、Jesthi, Pradipta K.、Sadhu, Kizhakethil M.

  DOI：——

  日期：——
• Hydroboration with Haloborane/Trialkylsilane Mixtures
  作者：Raman Soundararajan、Donald S. Matteson

  DOI：10.1021/om00009a018

  日期：1995.9

  Trialkylsilanes or dialkylsilanes react rapidly with boron trichloride in the absence of ethereal solvents or other nucleophiles to form unsolvated dichloroborane. If no substrate is present, dichloroborane disproportionates to trichloroborane and two geometric isomers of chloroborane dimer, which in turn yield monochlorodiborane and, slowly but irreversibly, diborane. All of the B-H compounds in the mixture except diborane are highly active hydroborating agents. With alkenes in the presence of sufficient boron trichloride, the products are alkyldichloroboranes. These are free from detectable contamination by dialkylchloroboranes unless more than 1 mol of hydride is present. Similar hydroboration of terminal acetylenes can be controlled to yield either (E)-1-(dichloroboryl)alkenes or 1,1-bis(dichloroboryl)alkanes, each free from significant contamination by the other. Alkyldichloroboranes with trialkylsilanes at 25 degrees C produce alkylmonochloroboranes, detected by B-11 NMR. 1,1-Bis(dichloroboryl)alkanes similarly yield 1,1-diborylalkane dimers. An alkylmonochloroborane can hydroborate a second alkene to form a dialkylchloroborane. For this purpose, differing alkyl groups may be introduced in either order, regardless of their relative steric properties. With 2 mol of trialkylsilane, alkyldichloroboranes are converted to alkylborane dimers. Boron tribromide and its bromoborane derivatives behave similarly to the chloro compounds in the examples tested.
• Expanding the scope of PNA-encoded libraries: divergent synthesis of libraries targeting cysteine, serine and metallo-proteases as well as tyrosine phosphatases
  作者：François Debaene、Julien A. Da Silva、Zbigniew Pianowski、Fernando J. Duran、Nicolas Winssinger

  DOI：10.1016/j.tet.2007.03.033

  日期：2007.7

  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.