3H-[1]Benzopyrano[4,3-c]isoxazole, 1,3a,4,9b-tetrahydro- | 120779-81-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3H-[1]Benzopyrano[4,3-c]isoxazole, 1,3a,4,9b-tetrahydro-
• 英文别名: 3,3a,4,9b-tetrahydro-1H-chromeno[4,3-c][1,2]oxazole
• CAS: 120779-81-9
• 化学式: C₁₀H₁₁NO₂
• 分子量: 177.203
• InChiKey: ZXMFDPAQTCFAEQ-UHFFFAOYSA-N

物化性质

• 熔点：
  178-180 °C
• 沸点：
  268.7±50.0 °C(Predicted)
• 密度：
  1.192±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  30.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3H-[1]Benzopyrano[4,3-c]isoxazole, 1,3a,4,9b-tetrahydro- 、 邻甲苯异氰酸酯 以 四氢呋喃 为溶剂， 生成 N-o-tolyl-3,3a,4,9b-tetrahydro-1H-chromeno[4,3-c]isoxazole-1-carboxamide
  参考文献：
  名称：

  N-Tetrahydrothiochromenoisoxazole-1-carboxamides as selective antagonists of cloned human 5-HT2B

  摘要：

  The serendipitous discovery of N-cyclohexyl-8-fluoro-3,3a,4,9b-tetrahydro-1H-thiochromeno[4,3-c]isoxazole-1-carboxamide as a selective human serotonin 5-HT2B antagonist with K-i of 42 +/- 5 nM is reported herein. A subsequent functional assay indicated little agonist activity compared to 5-HT itself. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.07.074
• 作为产物：
  描述：

  N-[(2-prop-2-enoxyphenyl)methylidene]hydroxylamine 以20%的产率得到3H-[1]Benzopyrano[4,3-c]isoxazole, 1,3a,4,9b-tetrahydro-
  参考文献：
  名称：

  分子内肟烯烃环加成。立体形成官能化的吡咯烷。

  摘要：

  具有适当位置的醛肟或酮肟链的烯丙胺经历热诱导的偶极环加成反应形成双环异恶唑烷，并立体定向引入三个立体中心。这提供了进入立体特异性官能化的吡咯烷的入口。

  DOI：

  10.1016/s0040-4039(00)80746-7

文献信息

• Synthesis of Functionalized Benzopyrans via Intramolecular 1,3-Dipolar Cycloaddition of Nitrile Oxides
  作者：Vipraja V. Vaidya、Karuna S. Wankhede、Manikrao M. Salunkhe、Girish K. Trivedi

  DOI：10.1080/00397910802138744

  日期：2008.6.27

  Abstract Various functionalized benzopyran derivatives have been synthesized in good yields by a sequence of reactions viz. intramolecular cyclization of nitrile oxides, reductive cleavage, and acetylation.

  摘要 通过一系列反应合成了各种功能化的苯并吡喃衍生物，收率良好。腈氧化物的分子内环化、还原裂解和乙酰化。
• [EN] TRICYCLIC COMPOUNDS AS INHIBITORS FOR THE PRODUCTION OF BETA-AMYLOID<br/>[FR] COMPOSÉS TRICYCLIQUES EN TANT QU'INHIBITEURS POUR LA PRODUCTION DE BÊTA-AMYLOÏDE
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2012162330A1

  公开（公告）日：2012-11-29

  Compounds of formula (I), including pharmaceutically acceptable salts thereof, are set forth herein: formula (I), wherein X is selected from the group of CH2, O, and NR2; m = 0 or 1; R1 at each instance is selected from the group of halogen, hydroxy, amino, C1-4alkylamino, C1-4dialkylamino, haloC1-4 alkyl, CN, C1-C6 alkyl or cycloalkyl, C1-C6 alkoxy, and C2-C4 alkynyl; L is a bond, -NHCO-, -NH-, or L and Z together can be absent; Z is a C6-C10- aryl group or a 5-10 membered heterocyclic group which can be further substituted with from 0-3 substituents selected from the group of halogen, haloC1-4 alkoxy, 4-methoxyphenyl, hydroxy, amino, C1-4alkylamino, C1-4dialkylamino, haloC1-4 alkyl, CN, C1-C6 alkyl or cycloalkyl, C1-C6 alkoxy, and C2-C4 alkynyl; R2 is selected from the group of hydrogen, benzyl, C1-C6 alkyl or cycloalkyl, C1-C6 alkoxy, acetyl, and methanesulfonyl; and R3, R4 and R5 are independently selected from hydrogen or C1-4alkyl.

  化合物的结构式（I），包括其药用盐，如下所示：结构式（I），其中X选自CH2、O和NR2的组中；m = 0或1；每个R1实例选自卤素、羟基、氨基、C1-4烷基氨基、C1-4二烷基氨基、卤代C1-4烷基、氰基、C1-C6烷基或环烷基、C1-C6烷氧基和C2-C4炔基的组中；L是键，-NHCO-，-NH-，或L和Z一起可以不存在；Z是C6-C10芳基或一个5-10成员杂环基，该基可以进一步取代，取代基选自卤素、卤代C1-4烷氧基、4-甲氧基苯基、羟基、氨基、C1-4烷基氨基、C1-4二烷基氨基、卤代C1-4烷基、氰基、C1-C6烷基或环烷基、C1-C6烷氧基和C2-C4炔基；R2选自氢、苄基、C1-C6烷基或环烷基、C1-C6烷氧基、乙酰基和甲磺酰基的组中；R3、R4和R5独立地选自氢或C1-4烷基。
• HASSNER, ALFRED;MAURYA, RAKESH;MESKO, ESZTER, TETRAHEDRON LETT., 29,(1988) N 41, C. 5313-5316
  作者：HASSNER, ALFRED、MAURYA, RAKESH、MESKO, ESZTER

  DOI：——

  日期：——
• N-Tetrahydrothiochromenoisoxazole-1-carboxamides as selective antagonists of cloned human 5-HT2B
  作者：Yoon Jin Kwon、Simon Saubern、James M. Macdonald、Xi-Ping Huang、Vincent Setola、Bryan L. Roth

  DOI：10.1016/j.bmcl.2010.07.074

  日期：2010.9

  The serendipitous discovery of N-cyclohexyl-8-fluoro-3,3a,4,9b-tetrahydro-1H-thiochromeno[4,3-c]isoxazole-1-carboxamide as a selective human serotonin 5-HT2B antagonist with K-i of 42 +/- 5 nM is reported herein. A subsequent functional assay indicated little agonist activity compared to 5-HT itself. (c) 2010 Elsevier Ltd. All rights reserved.
• Intramolecular oxime olefin cycloadditions. Stereospecific formation of functionalized pyrrolidines.
  作者：Alfred Hassner、Rakesh Maurya、Eszter Mesko

  DOI：10.1016/s0040-4039(00)80746-7

  日期：1988.1

  Allylamines possessing a properly positioned aldoxime or ketoxime chain undergo thermally induced dipolar cycloaddition to bicylic isoxazolidines, with stereospecific introduction of three stereo centers. This provides an entry into stereospecifically functionalized pyrrolidines.

  具有适当位置的醛肟或酮肟链的烯丙胺经历热诱导的偶极环加成反应形成双环异恶唑烷，并立体定向引入三个立体中心。这提供了进入立体特异性官能化的吡咯烷的入口。