3-(2-chlorophenyl)isoxazole | 25742-65-8

• 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: 3-(2-chlorophenyl)isoxazole
• 英文别名: 3-o-Chlorophenylisoxazol；3-(2-chlorophenyl)-1,2-oxazole
• CAS: 25742-65-8
• 化学式: C₉H₆ClNO
• 分子量: 179.606
• InChiKey: SPRITDNDMXTXIE-UHFFFAOYSA-N

物化性质

• 沸点：
  85 °C(Press: 0.3 Torr)
• 密度：
  1.258±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  1
• 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：

  3-(2-chlorophenyl)isoxazole 、 lithium diisopropyl amide 以 四氢呋喃 、 hexanes 为溶剂， 反应 1.0h， 以40%的产率得到2,6-bis(2-chlorophenyl)-3,7-diazatricyc[4.2.0.0(2,5)]octane-4,8-dione
  参考文献：
  名称：

  Effect of the aryl group substituent in the dimerization of 3-arylisoxazoles to syn 2,6-diaryl-3,7-diazatricyclo[4.2.0.02,5]octan-4,8-diones induced by LDA

  摘要：

  3-Arylisoxazoles react with LDA in THF at 0 degrees C affording syn-2,6-diaryl-3,7-diazatricyclo[4.2.0.0(2,5)]octan-4,8-diones (bis-azetidinones), via stereoselective dimerization of an azetinone anion intermediate. A fragmentation reaction affording arylnitriles may compete with electronic and steric effects of the substituent present in the aryl group being pivotal in determining the outcome of this reaction. An interesting behaviour with LDA of arylnitriles arising from the fragmentation reaction of some 3-arylisoxazoles was also observed. N,N-Diisopropylaminobenzonitriles were in fact formed (plausibly via a benzyne mechanism) from 3-(4-chlorophenyl)isoxazole and 3-(2-chlorophenyl)isoxazole, whereas 3-(2-methylphenyl)isoquinolin-1-amine was isolated starting from 3-(2-methylphenyl)isoxazole and LDA. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.09.063
• 作为产物：
  描述：

  3-(2-chlorophenyl)-5-hydroxy-2-isoxaline 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以90%的产率得到3-(2-chlorophenyl)isoxazole
  参考文献：
  名称：

  取代的苄腈氧化物与乙醛的烯醇酸根离子反应合成3-芳基-4,5-二氢-5-羟基-1,2-恶唑

  摘要：

  通过使取代的苄腈氧化物与乙醛的烯醇盐离子反应（由正丁基锂存在下已知的THF环还原定量地产生），可以生成许多3-芳基-4,5-二氢-5-羟基-1，2-高产率地分离了恶唑（以前未知，或者在两种情况下，仅通过不同的方法合成）。用一些常见的碱处理此类羟基异恶唑啉可使其以高收率转化成相应的异恶唑。

  DOI：

  10.1016/s0040-4020(01)86800-9

文献信息

• Polymer-Supported Vinyl Sulfone as an Efficient Reagent for the Synthesis of 3-Monosubstituted Isoxazoles
  作者：Guo-Jian Wu、Shou-Ri Sheng、Dan Li、Li-Fan Xu、Zhen-Zhong Huang

  DOI：10.1080/00397911.2012.762718

  日期：2013.11.17

  Abstract Polystyrene-supported vinyl sulfone reagent has been developed and used for solid-phase organic synthesis of 3-monosubstituted isoxazoles by 1,3-dipolar cycloaddition reaction with nitrile oxides and subsequent cleavage from the polymer support through an elimination reaction in the presence of potassium tert-butoxide. The advantages of this method include straightforward operation, good yield

  摘要 聚苯乙烯负载的乙烯基砜试剂已被开发并用于固相有机合成 3-单取代异恶唑，通过与腈氧化物的 1,3-偶极环加成反应，然后在钾存在下通过消除反应从聚合物载体上裂解。叔丁醇。该方法的优点是操作简单、收率好、粗品纯度高。图形概要
• Efficient and Regioselective One-Pot Synthesis of 3-Substituted and 3,5-Disubstituted Isoxazoles
  作者：Shibing Tang、Jinmei He、Yongquan Sun、Liuer He、Xuegong She

  DOI：10.1021/ol901626n

  日期：2009.9.3

  A series of 3-substituted and 3,5-disubstituted isoxazoles have been efficiently synthesized in moderate to excellent yields by the reaction of N-hydroxyl-4-toluenesulfonamide with α,β-unsaturated aldehydes/ketones. This novel strategy is associated with readily available starting materials, mild conditions, high regioselectivity, and wide scope.

  通过N-羟基-4-甲苯磺酰胺与α，β-不饱和醛/酮的反应，已经以中等至优异的产率有效地合成了一系列3-取代的和3，5-二取代的异恶唑。这种新颖的策略与容易获得的起始原料，温和的条件，较高的区域选择性和广泛的范围有关。
• Synthesis of 3-aryl-4, 5-dihydro-5-hydroxy-1,2-oxazoles by reaction of substituted benzonitrile oxides with the enolate ion of acetaldehyde
  作者：L. Di Nunno、L. Di Nunno、A. Scilimati

  DOI：10.1016/s0040-4020(01)86800-9

  日期：1987.1

  By reaction of substituted benzonitrile oxides with the enolate ion of acetaldehyde (quantitatively generated by the known cycloreversion of THF in the presence of n-butyllithium) a number of 3-aryl-4,5-dihydro-5-hydroxy-1, 2-oxazoles (previously unknown or, in two cases, only synthesized by different procedures) have been isolated in high yields. Treatment of such hydroxyisoxazolines with some common

  通过使取代的苄腈氧化物与乙醛的烯醇盐离子反应（由正丁基锂存在下已知的THF环还原定量地产生），可以生成许多3-芳基-4,5-二氢-5-羟基-1，2-高产率地分离了恶唑（以前未知，或者在两种情况下，仅通过不同的方法合成）。用一些常见的碱处理此类羟基异恶唑啉可使其以高收率转化成相应的异恶唑。
• Studies in isoxazole chemistry. II. Isoxazoles from the Δ²-isoxazolin-5-ols and their acetates
  作者：R. G. Micetich

  DOI：10.1139/v70-075

  日期：1970.2.1

  Various 3-substituted-5-acetoxy-Δ2-isoxazolines were made by the 1,3-dipolar cycloaddition of nitrile oxides to vinyl acetate or isopropenyl acetate. These compounds were readily converted in high yield to 3-substituted isoxazoles or 3-substituted-5-methylisoxazoles respectively, on heating. Treatment of the 3-substituted-5-acetoxy-Δ2-isoxazolines with sodium hydroxide in methanol gave rise to the

  通过腈氧化物与乙酸乙烯酯或乙酸异丙烯酯的 1,3-偶极环加成反应制备了各种 3-取代-5-乙酰氧基-Δ2-异恶唑啉。这些化合物在加热时很容易以高产率分别转化为 3-取代的异恶唑或 3-取代的 5-甲基异恶唑。在甲醇中用氢氧化钠处理 3-取代-5-乙酰氧基-Δ2-异恶唑啉在酸化后产生稳定的 Δ2-异恶唑啉-5-醇。这些化合物也可以通过单独加热或在亚硫酰氯的存在下更好地转化为 3-取代的异恶唑。讨论了这些化合物的核磁共振谱。
• Triazole derivatives as tachykinin receptor antagonists
  申请人：Amegadzie Kudzovi Albert

  公开号：US20050239786A1

  公开（公告）日：2005-10-27

  This application relates to a compound of Formula (I) or a pharmaceutically acceptable salt thereof, pharmaceutical compositions thereof, and its use as an inhibitor of the NK-1 subtype of tachykinin receptors, as well as a process for its preparation and intermediates therefor. (I) wherein: D is a C 1 -C 3 alkane-diyl; R 1 is phenyl, which is optionally substituted with one to three substitutents independently selected from the group consisting of halo, C 1 -C 4 alkyl, C 1 -C 4 alkoxy, cyano, difluoromethyl, trifluoromethyl, and trifluoromethoxy; R 4 is a radical selected from the group consisting of: (IA), (IB), (IC), (ID), (IE), (IF), (IG), (IH)

  本申请涉及化合物I式或其药学上可接受的盐，其药物组合物以及其作为tachykinin受体NK-1亚型的抑制剂的用途，以及其制备过程和中间体。其中：D是C1-C3烷基二亚基；R1是苯基，可选地取代为一个至三个取代基，独立地选自卤素，C1-C4烷基，C1-C4烷氧基，氰基，二氟甲基，三氟甲基和三氟甲氧基的群；R4是从群 consisting of: (IA), (IB), (IC), (ID), (IE), (IF), (IG), (IH)中选择的基团。