4-溴苯硼酸N-甲基二乙醇胺酯 | 115247-41-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-溴苯硼酸N-甲基二乙醇胺酯
• 英文名称: 4-bromo N-methyl-diethanolamine phenylboronate
• 英文别名: (4-bromophenyl)boronic acid N-methyl-O,O-diethanolamine ester；4-bromobenzeneboronic acid N-methyldiethanolamine cyclic ester；2-(4-bromophenyl)-6-methyl-1,3,6,2-dioxyazaborocane；2-(4-bromo-phenyl)-6-methyl-[1,3,6,2]dioxazaborocane；p-bromo-benzeneboronic acid, (methylimino)diethylene ester；4-bromobenzeneboronic acid N-methyldiethanolamine ester；2-(4-Brom-phenyl)-6-methyl-[1,3,6,2]dioxazaborocan；2-(4-Bromophenyl)-6-methyl-1,3,6,2-dioxazaborocane
• CAS: 115247-41-1
• 化学式: C₁₁H₁₅BBrNO₂
• 分子量: 283.961
• InChiKey: OSYBCIKXYVRFGE-UHFFFAOYSA-N

物化性质

• 沸点：
  364.719±37.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.368±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.12
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温，惰性气氛

反应信息

• 作为反应物：
  描述：

  4-溴苯硼酸N-甲基二乙醇胺酯 在 N-氯代丁二酰亚胺 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 2.25h， 生成 4-chlorosulfonyl-phenylboronic acid N-methyl-diethanolamine ester
  参考文献：
  名称：

  Synthesis of Sulfonyl Chlorides of Phenylboronic Acids

  摘要：

  苯基硼酸酯的磺酰氯可通过选择性锂化溴代N-甲基二乙醇胺苯基硼酸盐，生成锂亚磺酰苯基硼酸盐中间体，再通过与N-氯代琥珀酰亚胺氧化，得到目标磺酰氯。这些新的试剂在制备苯基硼酸的磺酰胺以及其他化合物中非常有用，这些化合物可用于钯(0)催化的交叉偶联反应。此外，它们还具有作为生理pKa条件下碳水化合物结合剂的潜力。

  DOI：

  10.1055/s-2004-817758
• 作为产物：
  描述：

  N-甲基二乙醇胺 、 4-溴苯硼酸 生成 4-溴苯硼酸N-甲基二乙醇胺酯
  参考文献：
  名称：

  The Synthesis of p-Vinylphenylboronic Acid and Some of its Derivatives

  摘要：

  DOI：

  10.1021/ja01512a018

文献信息

• [EN] HALO SULFONYL ARYL BORONATES<br/>[FR] HALO SULFONYL ARYL BORONATES
  申请人：NOVO NORDISK AS

  公开号：WO2004041833A1

  公开（公告）日：2004-05-21

  The present invention relates to halo sulfonyl aryl boronates of the general formula (I): wherein Arylene designates a carbocyclic or heterocyclic, aromatic ring system comprising 1-3 rings; R1, R2 and R3 are, independently, hydrogen, C1-6alkyl, C1-6alkoxy, halogen, nitro, cyano or phenyl;X is fluoro, chloro or bromo; and Y is a boroxine moiety attached via a bond from Arylene to one of the boron atoms of a boroxine ring which ring has a group of the formula -Arylene(R1)(R2)(R3)SO2X, wherein Arylene, R1, R2, R3 and X are as defined above, at each of the other two boron atoms of the boroxine ring, or Y is a boronic acid group or a boronic ester group.The invention also relates to the preparation of the compounds of formula (I) and to their use in organic synthesis.

  本发明涉及一般式(I)的卤磺酰基芳基硼酸酯，其中芳烃代表一个包含1-3个环的碳环或杂环芳香环系统；R1、R2和R3分别是氢、C1-6烷基、C1-6烷氧基、卤素、硝基、氰基或苯基；X是氟、氯或溴；Y是通过一种键连接到芳烃上的硼氧杂环部分，该硼氧杂环具有一个式为-Arylene(R1)(R2)(R3)SO2X的基团，其中Arylene、R1、R2、R3和X如上定义，在硼氧杂环的另外两个硼原子上，或Y是硼酸基团或硼酯基团。该发明还涉及一般式(I)化合物的制备以及它们在有机合成中的应用。
• Synthesis and Activity of a Novel Series of 3-Biarylquinuclidine Squalene Synthase Inhibitors
  作者：George R. Brown、David S. Clarke、Alan J. Foubister、Susan Freeman、Peter J. Harrison、Michael C. Johnson、Keith B. Mallion、John McCormick、Fergus McTaggart、Alan C. Reid、Graham J. Smith、Melvyn J. Taylor

  DOI：10.1021/jm950907l

  日期：1996.1.1

  Quinuclidines with a 3-biaryl substituent are a new class of potent, orally active squalene synthase (SQS) inhibitors. Variants around these rigid structures indicate key structural requirements for cationic SQS inhibitors. Thus the lower in vitro potency found for quinuclidines bearing 3-substituents, which did not overlay the biphenyl group of 3-(biphenyl-4-yl)-3-hydroxyquinuclidine (2) (IC50 = 16

  具有3-联芳基取代基的喹核苷是一类新的有效的，口服活性的角鲨烯合酶（SQS）抑制剂。这些刚性结构周围的变化指示出阳离子SQS抑制剂的关键结构要求。因此，暗示了带有3个取代基的喹核苷的体外效价较低，该奎尼啶没有覆盖3-（联苯基-4-基）-3-羟基喹核苷（2）的联苯基团（IC50 = 16 nM，大鼠微粒体SQS）。 3取代基的方向性要求。类似地，3-三联苯类似物6的较低效能（IC50 = 370 nM）表明该取代基的尺寸受到限制。在具有奎宁环和联苯环之间连接基团的化合物中，亲脂性较低的连接基团的耐受性较差（例如，17，CH2CH2，IC50 = 5 nM与19，NHCO，IC50 = 1.2 microM）。用更具极性的吡啶杂环取代2的远端苯环会导致体外效能降低。通常，大鼠体内的良好体内活性仅限于3-羟基类似物，其中3- [4-（吡啶-4-基）苯基]衍生物39（IC50 = 161 nM）显示出最佳的抑制作用（口服给药后）
• Synthesis and evaluation of thiazolidinedione and dioxazaborocane analogues as inhibitors of AI-2 quorum sensing in Vibrio harveyi
  作者：Gilles Brackman、Abed Al Aziz Al Quntar、Claes D. Enk、Izet Karalic、Hans J. Nelis、Serge Van Calenbergh、Morris Srebnik、Tom Coenye

  DOI：10.1016/j.bmc.2012.11.055

  日期：2013.2

  Two focused libraries based on two types of compounds, that is, thiazolidinediones and dioxazaborocanes were designed. Structural resemblances can be found between thiazolidinediones and well-known furanone type quorum sensing (QS) inhibitors such as N-acylaminofuranones, and/or acyl-homoserine lactone signaling molecules, while dioxazaborocanes structurally resemble previously reported oxazaborolidine derivatives which antagonized autoinducer 2 (AI-2) binding to its receptor. Because of this, we hypothesized that these compounds could affect AI-2 QS in Vibrio harveyi. Although all compounds blocked QS, the thiazolidinediones were the most active AI-2 QS inhibitors, with EC50 values in the low micromolar range. Their mechanism of inhibition was elucidated by measuring the effect on bioluminescence in a series of V. harveyi QS mutants and by DNA-binding assays with purified LuxR protein. The active compounds neither affected bioluminescence as such nor the production of AI-2. Instead, our results indicate that the thiazolidinediones blocked AI-2 QS in V. harveyi by decreasing the DNA-binding ability of LuxR. In addition, several dioxazaborocanes were found to block AI-2 QS by targeting LuxPQ. (C) 2012 Elsevier Ltd. All rights reserved.
• N-ARYL-SUBSTITUTED CYCLIC AMINE DERIVATIVE AND MEDICINE CONTAINING THE SAME AS ACTIVE INGREDIENT
  申请人：Eisai R&D Management Co., Ltd.

  公开号：EP1375496B1

  公开（公告）日：2007-07-04