6-Chlorbenzisoxazol | 39835-07-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并异恶唑
• 英文名称: 6-Chlorbenzisoxazol
• 英文别名: 6-Chloro-1,2-benzisoxazole；6-chloro-1,2-benzoxazole
• CAS: 39835-07-9
• 化学式: C₇H₄ClNO
• mdl: MFCD06659633
• 分子量: 153.568
• InChiKey: WXVYFIRLSWWDBP-UHFFFAOYSA-N

物化性质

• 沸点：
  251.2±13.0 °C(Predicted)
• 密度：
  1.377±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-Chlorbenzisoxazol 在 硫酸 、 硝酸 作用下， 反应 0.5h， 以61.9%的产率得到5-nitro-6-chlorobenzisoxazole
  参考文献：
  名称：

  Toward bifunctional antibody catalysis

  摘要：

  Antibodies that catalyze the deprotonation of unactivated benzisoxazoles to give the corresponding salicylonitriles were prepared using as antigen a 2-aminobenzimidazolium derivative coupled to a carrier protein via its benzene ring. The hapten was designed to induce an antibody binding site with both a base and an acid, in position to initiate proton transfer and stabilize developing negative charge at the phenoxide leaving group, respectively. Consistent with this design, the catalysts exhibit bell-shaped pH-rate profiles, while chemical modification identified several functional groups that could participate in bifunctional catalysis. One of the antibodies, 13G5, is particularly notable in catalyzing the elimination of 6-glutaramidebenzisoxazole with a > 10(5)-fold rate acceleration over background and an effective molarity of > 10(4) M for its catalytic base. These properties compare favorably to the efficiencies achieved by the best previously characterized antibodies with substantially more reactive substrates. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.05.071
• 作为产物：
  描述：

  4-chloro-2-hydroxybenzaldehyde oxime 在 三苯基膦 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 为溶剂， 反应 0.02h， 生成 6-Chlorbenzisoxazol
  参考文献：
  名称：

  通过氮杂氧基烯丙基阳离子与1,2-苯并恶唑的级联反应有效合成恶唑啉。

  摘要：

  已经实现了在原位形成的氮杂烯丙基阳离子的C和O末端与1,2-苯并恶唑之间的正式[3 + 2]环加成反应。这种一锅法环加成法为在温和条件下以高收率合成恶唑啉提供了有效而实用的途径。标题产物表现出独特的荧光性质。

  DOI：

  10.1039/c9ob01366k

文献信息

• Gold-Catalyzed Michael-Type Reactions and [4 + 2]-Annulations between Propiolates and 1,2-Benzisoxazoles with Ester-Directed Chemoselectivity
  作者：Yashwant Bhaskar Pandit、Rajkumar Lalji Sahani、Rai-Shung Liu

  DOI：10.1021/acs.orglett.8b02663

  日期：2018.11.2

  This work reports gold-catalyzed reactions between 1,2-benzisoxazoles and propiolate derivatives with ester-controlled chemoselectivity. For ethyl propiolates 1′, their gold-catalyzed reactions afforded Michael-type products 4, whereas tert-butyl propiolates 1 preferably underwent [4 + 2]-annulations, further yielding 6H-1,3-oxazin-6-one derivatives 3.

  这项工作报告了1，2-苯并恶唑与丙酸酯衍生物之间的金催化反应，并具有酯控制的化学选择性。对于丙酸乙酯1'，其金催化的反应得到迈克尔型产物4，而丙酸叔丁酯1优选经历[4 + 2]环化，进一步产生6 H -1,3-恶嗪-6-一衍生物3。
• 一种2,3-二酰基喹啉类化合物的合成方法
  申请人：江南大学

  公开号：CN112552235A

  公开（公告）日：2021-03-26

  本发明公开了一种2,3‑二酰基喹啉类化合物的合成方法，将式Ι所示的苯并[c]异噁唑类化合物、式Ⅱ所示的铵盐类化合物溶于有机溶剂中，在铜催化剂和碱试剂的作用下进行反应，将所得反应液提纯即得到式Ⅲ所示的2,3‑二酰基喹啉类化合物。本发明使用的原料价格低廉，催化剂廉价易得且用量少，操作简单，底物适用范围较广。
• Stereoselective Synthesis of (Z)-Allyl Alcohols through Coinage-Metal-Catalyzed Nucleophilic Addition of Benzo[d]isoxazoles with Unactivated Propargyl Alcohols
  作者：Zhiyuan Chen、Wenjin Wu、Tiantian Zheng、Jie Tan、Shouzhi Pu

  DOI：10.1055/s-0037-1611828

  日期：2019.7

  The Au/Ag-cocatalyzed stereoselective addition reaction of cyanophenol anion species generated in situ with unactivated propargyl alcohols to produce functionalized (Z)-allyl alcohols in mostly good yields is reported. Benzo[d]isoxazoles were found to be excellent building blocks for the production of highly reactive cyanophenol anions from Kemp elimination reactions, thus serving as a masked benzonitrile

  据报道，Au/Ag 共催化的氰基苯酚阴离子物种与未活化的炔丙醇发生立体选择性加成反应，以大多数良好的收率生产官能化 (Z)-烯丙醇。发现苯并 [d] 异恶唑是通过 Kemp 消除反应生产高反应性氰基苯酚阴离子的极好结构单元，因此可用作制备有机腈衍生物的掩蔽苯甲腈源。发现银盐与金催化剂的结合对于这种转化的成功是必要的。
• Isoxazole derivatives for use as cerebro-active drugs and central muscle relaxants
  申请人：Sankyo Company Limited

  公开号：EP0335723B1

  公开（公告）日：1991-12-04
• Gold-Catalyzed [5+2]- and [5+1]-Annulations between Ynamides and 1,2-Benzisoxazoles with Ligand-Controlled Chemoselectivity
  作者：Prakash D. Jadhav、Xin Lu、Rai-Shung Liu

  DOI：10.1021/acscatal.8b03011

  日期：2018.10.5

  This work describes two distinct annulations between ynamides and 1,2-benzisoxazoles with chemo-selectivity controlled by ligands. With IPrAuCl/AgNTf2, aryl-substituted ynamides undergo [5+2]-annulation reactions, whereas P(t-Bu)(2)(o-biphenyl)AuCl/AgNTf2 alters the chemoselectivity of the same ynamides to implement [5+1]-annulation reactions. C-13-Labeling experiments confirm that a 1,2-sulfonamide shift is involved in the [5+1]-annulation process. A plausible mechanism is postulated to rationalize the mechanisms of the two annulations.