2,2-di-p-tolyl-1,3,2-oxazaborolidin-3-ium-2-uide

• 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-di-p-tolyl-1,3,2-oxazaborolidin-3-ium-2-uide
• 英文别名: 2-((di-o-tolylboryl)oxy)ethanamine；2-aminoethyl di(p-tolyl)borinate；B,B-Bis-<4-tolyl>-boroxazolidin；B,B-Di-p-tolyl-boroxazolidin；2,2-di-p-tolyl-4,5-dihydro-[1,3,2]oxazaborole；di(p-tolyl)borinic acid ethanolamine complex；2,2-Bis(4-methylphenyl)-1-oxa-3-azonia-2-boranuidacyclopentane；2,2-bis(4-methylphenyl)-1-oxa-3-azonia-2-boranuidacyclopentane
• 化学式: C₁₆H₂₀BNO
• 分子量: 253.152
• InChiKey: APGXLCFFSIYZGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.45
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  25.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (4-CH3C6H4)2B-N(i-C3H7)2 以 甲醇 、 乙醚 为溶剂， 反应 1.0h， 生成 2,2-di-p-tolyl-1,3,2-oxazaborolidin-3-ium-2-uide
  参考文献：
  名称：

  通过胺-硼烷配合物的直接芳基化反应生成的硼酸：空气和水稳定的硼源

  摘要：

  摘要 使用胺-硼烷配合物作为对水和空气不敏感的硼化剂，可以优化硼酸和硼酸酯的合成。该反应在适宜的条件下使用非低温温度进行，并且没有快速色谱，并且没有硼杂质。该反应通过串联脱氢-双重加成机理进行。 使用胺-硼烷配合物作为对水和空气不敏感的硼化剂，可以优化硼酸和硼酸酯的合成。该反应在适宜的条件下使用非低温温度进行，并且没有快速色谱，并且没有硼杂质。该反应通过串联脱氢-双重加成机理进行。

  DOI：

  10.1055/s-0036-1588345

文献信息

• Synthesis of Borinic Acids and Borinate Adducts Using Diisopropylaminoborane
  作者：Ludovic Marciasini、Bastien Cacciuttolo、Michel Vaultier、Mathieu Pucheault

  DOI：10.1021/acs.orglett.5b01620

  日期：2015.7.17

  situ formation of aryl Grignard under Barbier condition and diisopropylaminoborane as boron source allows a complete control of the addition onto the boron electrophile. Analytically pure borinic acid derivatives were produced at the gram scale without column chromatography and isolated as borinates adducts, with ethanolamine or 8-hydroxyquinoline, after workup.

  在Barbier条件下原位形成芳基格氏试剂，并用二异丙基氨基硼烷作为硼源，可以完全控制向亲电硼的添加。在没有柱色谱的情况下，以克级产生分析纯的硼酸衍生物，并在后处理后与乙醇胺或8-羟基喹啉分离为硼酸酯加合物。
• Synthesis and Characterization of Store-Operated Calcium Entry Inhibitors Active in the Submicromolar Range
  作者：Camille Le Guilcher、Tomas Luyten、Jan B. Parys、Mathieu Pucheault、Olivier Dellis

  DOI：10.3390/ijms21249777

  日期：——

  The store-operated calcium entry, better known as SOCE, forms the main Ca2+ influx pathway in non-excitable cells, especially in leukocytes, where it is required for cell activation and the immune response. During the past decades, several inhibitors were developed, but they lack specificity or efficacy. From the non-specific SOCE inhibitor 2-aminoethyl diphenylborinate (2-APB), we synthetized 16 new analogues by replacing/modifying the phenyl groups. Among them, our compound P11 showed the best inhibitory capacity with a Ki ≈ 75 nM. Furthermore, below 1 µM, P11 was devoid of any inhibitory activity on the two other main cellular targets of 2-APB, the IP3 receptors, and the SERCA pumps. Interestingly, Jurkat T cells secrete interleukin-2 under phytohemagglutinin stimulation but undergo cell death and stop IL-2 synthesis when stimulated in the presence of increasing P11 concentrations. Thus, P11 could represent the first member of a new and potent family of immunosuppressors.

  存储操作的钙离子进入，更为人熟知的是SOCE，在非兴奋性细胞中形成主要的Ca2+流入途径，特别是在白细胞中，这对于细胞激活和免疫应答是必需的。在过去的几十年里，开发了几种抑制剂，但它们缺乏特异性或有效性。从非特异性的SOCE抑制剂2-氨乙基二苯硼烷(2-APB)出发，我们通过替换/修改苯基合成了16个新的类似物。其中，我们的化合物P11表现出最佳的抑制能力，Ki约为75 nM。此外，在1 µM以下，P11对2-APB的另外两个主要细胞靶点，即IP3受体和SERCA泵，均没有任何抑制活性。有趣的是，Jurkat T细胞在植物血凝素刺激下分泌白细胞介素-2，但在存在逐渐增加的P11浓度的刺激下，会发生细胞死亡并停止IL-2的合成。因此，P11可能代表了一类新的、强效的免疫抑制剂家族的第一成员。
• Development of a Telescoped Process for Preparation of N,O-Chelated Diarylborinates
  作者：Changwei Guan、Lingyun Huang、Chao Ren、Gang Zou

  DOI：10.1021/acs.oprd.8b00109

  日期：2018.7.20

  telescoped process has been developed for practical preparation of N,O-chelated four-coordinate diarylborinates via direct reaction of N,O-chelate ligands with a diarylborinate solution prepared by removal of magnesium via precipitation from a one-pot reaction of aryl bromides, magnesium, and tributylborate. Ten N,O-chelated diarylborinates of representative N,O-chelate ligands of 2-picolinic acid, quinolin-8-ol

  已经开发出一种望远镜方法，用于通过N，O-螯合物的配体与二芳基硼酸酯溶液的直接反应实际制备N，O-螯合的四配位二芳基硼酸酯，该溶液是通过一锅法从芳基溴化物的沉淀中除去镁而制得的，镁和硼酸三丁酯。可以容易地以高收率容易地获得2-个吡啶甲酸，喹啉-8-醇，N-二甲基甘氨酸和氨基醇的代表性N，O-螯合物的十个N，O-螯合的二芳基硼酸酯。伸缩过程不仅减少了化学废物，避免了对二芳基硼酸的繁琐纯化，而且消除了格氏试剂的处理，并提高了与酸敏感基团的相容性。
• The reactions of diborane with aryl-organotin compounds
  作者：G.M. Pickles、T. Spencer、F.G. Thorpe、A.B. Chopa、J.C. Podesta

  DOI：10.1016/s0022-328x(00)98667-4

  日期：1984.1

  A number of tetraaryltin compounds, Ar4Sn (where Ar = phenyl, o- and p-tolyl, and p-chlorophenyl) and triphenyltin compounds, Ph3SnX (where X = Cl, H, OH, OCOCH3, and OCOCF3) have been treated with diborane in tetrahydrofuran. Transmetallation occurs in which one or more aryl groups are transferred to boron. The organoboron intermediates give phenols upon oxidation and boronic and borinic acids upon

  许多四芳基锡化合物Ar 4 Sn（其中Ar =苯基，邻甲苯基和对甲苯基，以及对氯苯基）和三苯基锡化合物Ph 3 SnX（其中X = Cl，H，OH，OCOCH 3和OCOCF 3）已在四氢呋喃中用乙硼烷处理过。发生金属转移，其中一个或多个芳基转移到硼上。有机硼中间体在氧化时生成苯酚，在水解时生成硼酸和硼酸。还已经分离出有机硼烷的吡啶配合物。
• Design, synthesis and pharmacological characterization of analogs of 2-aminoethyl diphenylborinate (2-APB), a known store-operated calcium channel blocker, for inhibition of TRPV6-mediated calcium transport
  作者：Alexandre Hofer、Gergely Kovacs、Anna Zappatini、Michele Leuenberger、Matthias A. Hediger、Martin Lochner

  DOI：10.1016/j.bmc.2013.03.037

  日期：2013.6

  2-Aminoethyl diphenylborinate (2-APB) is a known modulator of the IP3 receptor, the calcium ATPase SERCA, the calcium release-activated calcium channel Orai and TRP channels. More recently, it was shown that 2-APB is an efficient inhibitor of the epithelial calcium channel TRPV6 which is overexpressed in prostate cancer. We have conducted a structure-activity relationship study of 2-APB congeners to understand their inhibitory mode of action on TRPV6. Whereas modifying the aminoethyl moiety did not significantly change TRPV6 inhibition, substitution of the phenyl rings of 2-APB did. Our data show that the diaryl borinate moiety is required for biological activity and that the substitution pattern of the aryl rings can influence TRPV6 versus SOCE inhibition. We have also discovered that 2-APB is hydrolyzed and transesterified within minutes in solution. (C) 2013 Elsevier Ltd. All rights reserved.