5-methyl-3-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoxazole | 374715-24-9

• 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: 5-methyl-3-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoxazole
• 英文别名: 2-(3-Phenyl-5-methylisoxazole-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane；5-methyl-3-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-oxazole
• CAS: 374715-24-9
• 化学式: C₁₆H₂₀BNO₃
• 分子量: 285.151
• InChiKey: YFEHXVPDKIFJTG-UHFFFAOYSA-N

物化性质

• 沸点：
  424.5±45.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.95
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  44.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-溴苯磺酰胺 、 5-methyl-3-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoxazole 在 potassium phosphate 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 作用下， 以 1,4-二氧六环 为溶剂， 反应 21.0h， 以100%的产率得到伐地考昔
  参考文献：
  名称：

  Investigation of the scope of a [3+2] cycloaddition approach to isoxazole boronic esters

  摘要：

  The [3 + 2] cycloaddition reaction of nitrile oxides and alkynylboronates provides direct access to a wide variety of isoxazole boronic esters. Specifically, this technique has been employed to generate trisubstituted isoxazole 4-boronates and disubstituted isoxazoles where the boronic ester moiety can be installed at C-4 or C-5 with high levels of regiocontrol. The application of this methodology in the synthesis of non-steroidal antiinflammatory agents is also described. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.05.015
• 作为产物：
  描述：

  苯甲酰氯 在 吡啶 、 iron(III) chloride 、 [(IPr)Au](trifluoroacetate) 、 盐酸羟胺 、 sodium sulfate 、 三苯基膦 作用下， 以 甲醇 、 硝基甲烷 、 甲苯 为溶剂， 反应 33.5h， 生成 5-methyl-3-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoxazole
  参考文献：
  名称：

  Oxyboration with and without a Catalyst: Borylated Isoxazoles via B–O σ-Bond Addition

  摘要：

  Herein we report an oxyboration reaction with activated substrates that employs B-O sigma bond additions to C-C pi bonds to form borylated isoxazoles, which are potential building blocks for drug discovery. Although this reaction can be effectively catalyzed by gold, it is the first example of uncatalyzed oxyboration of C-C pi bonds by B-O sigma bonds-and only the second example that is catalyzed. This oxyboration reaction is tolerant of groups incompatible with alternative lithiation/borylation and palladium-catalyzed C-H activation/borylation technologies for the synthesis of borylated isoxazoles.

  DOI：

  10.1021/acs.orglett.5b03530

文献信息

• A regioselective cycloaddition route to isoxazoleboronic esters
  作者：Mark W. Davies、Robert A. J. Wybrow、Joseph P. A. Harrity、Christopher N. Johnson

  DOI：10.1039/b103319k

  日期：——

  Alkynylboronates participate in 1,3-dipolar cycloaddition reactions with nitrile oxides to provide isoxazoleboronic esters with excellent levels of regiocontrol; additionally, these potentially valuable synthetic intermediates have been shown to participate efficiently in Suzuki coupling reactions.

  炔基硼酸盐能够参与与腈氧化物的1,3-偶极环加成反应，提供具有优异区域控制性的异恶唑硼酸酯；此外，这些被证明具有潜在价值的合成中间体还能高效参与铃木偶联反应。
• Large conductance calcium-activated k channel opener
  申请人：Imanishi Yasuhiro

  公开号：US20070060629A1

  公开（公告）日：2007-03-15

  The present invention provides a large conductance calcium-activated K channel opener comprising a compound of the formula (I): wherein R 1 and R 3 are each sulfonamide, carbamoyl, acyl, amino, and the like, m and n are each 0 to 2, R 2 and R 4 are each cyano, nitro, hydroxyl, an alkoxy, a halogen, or an alkyl, Ring A is benzene or a heterocyclic ring, Ring B is benzene, a heterocyclic ring, a cycloalkane etc, and Ring Q is pyrazole or isoxazole, or a pharmaceutically acceptable salt thereof as an active ingredient.

  本发明提供了一种大导电性钙激活K通道开放剂，其包括以下式子（I）的化合物：其中R1和R3各自为磺酰胺基，氨基甲酰基，酰基，氨基等，m和n各自为0到2，R2和R4各自为氰基，硝基，羟基，烷氧基，卤素或烷基，环A为苯环或杂环，环B为苯环，杂环，环己烷等，环Q为吡唑环或异噁唑环，或其药学上可接受的盐作为活性成分。
• [EN] LARGE CONDUCTANCE CALCIUM-ACTIVATED K CHANNEL OPENER<br/>[FR] AGENT D'OUVERTURE DE CANAUX K ACTIVES PAR LE CALCIUM A CONDUCTANCE ELEVEE
  申请人：TANABE SEIYAKU CO

  公开号：WO2005037271A3

  公开（公告）日：2005-09-01
• Oxyboration with and without a Catalyst: Borylated Isoxazoles via B–O σ-Bond Addition
  作者：Kim N. Tu、Joshua J. Hirner、Suzanne A. Blum

  DOI：10.1021/acs.orglett.5b03530

  日期：2016.2.5

  Herein we report an oxyboration reaction with activated substrates that employs B-O sigma bond additions to C-C pi bonds to form borylated isoxazoles, which are potential building blocks for drug discovery. Although this reaction can be effectively catalyzed by gold, it is the first example of uncatalyzed oxyboration of C-C pi bonds by B-O sigma bonds-and only the second example that is catalyzed. This oxyboration reaction is tolerant of groups incompatible with alternative lithiation/borylation and palladium-catalyzed C-H activation/borylation technologies for the synthesis of borylated isoxazoles.
• Investigation of the scope of a [3+2] cycloaddition approach to isoxazole boronic esters
  作者：Jane E. Moore、Mark W. Davies、Katharine M. Goodenough、Robert A.J. Wybrow、Mark York、Christopher N. Johnson、Joseph P.A. Harrity

  DOI：10.1016/j.tet.2005.05.015

  日期：2005.7

  The [3 + 2] cycloaddition reaction of nitrile oxides and alkynylboronates provides direct access to a wide variety of isoxazole boronic esters. Specifically, this technique has been employed to generate trisubstituted isoxazole 4-boronates and disubstituted isoxazoles where the boronic ester moiety can be installed at C-4 or C-5 with high levels of regiocontrol. The application of this methodology in the synthesis of non-steroidal antiinflammatory agents is also described. (c) 2005 Elsevier Ltd. All rights reserved.