6-phenyl-2,3,4,5-tetrahydrofuranyl<3,4-c>isoxazole | 120783-57-5

• 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: 6-phenyl-2,3,4,5-tetrahydrofuranyl<3,4-c>isoxazole
• 英文别名: (+/-)-6-Phenyl-4H,6H-furo<3,4-c>isoxazole；6-phenyl-4H,6H-furo[3,4-c]isoxazole；6-Phenyl-4,6-dihydrofuro[3,4-c][1,2]oxazole
• CAS: 120783-57-5
• 化学式: C₁₁H₉NO₂
• 分子量: 187.198
• InChiKey: XAALMDNPDNDAGU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  35.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯乙醛肟 在 sodium hypochlorite 、 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 四氯化碳 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 6-phenyl-2,3,4,5-tetrahydrofuranyl<3,4-c>isoxazole
  参考文献：
  名称：

  Cycloadditions. 41. Conversion of unsaturated alcohols into functionalized tetrahydrofurans and tetrahydropyrans via nitrile oxide dipolar cycloadditions

  摘要：

  DOI：

  10.1021/jo00283a021

文献信息

• Formation of functionalized cyclic ethers by intramolecular nitrile oxide cycloadditions
  作者：Albert Padwa、Ugo Chiacchio、Dennis C. Dean、Allen M. Schoffstall、Alfred Hassner、K.S.K. Murthy

  DOI：10.1016/s0040-4039(00)80447-5

  日期：1988.1

  The reaction of O-trimethylsilyl α-bromo aldoximes with unsaturated alcohols produces oximino ethers which can be readily oxidized with sodium hypochlorite. The transient nitrile oxide intermediate formed undergoes spontaneous cyclization affording fused isoxazolines. MM2 calculations help rationalize the observed stereoselectivity.

  O-三甲基甲硅烷基的α-溴代醛肟与不饱和醇的反应产生了肟基醚，其易于被次氯酸钠氧化。形成的瞬态一氧化二氮中间体经过自发环化，生成稠合的异恶唑啉。MM2计算有助于合理化观察到的立体选择性。
• One-pot synthesis of the hydroximoyl chlorides and [3.3.0] bicyclic compounds from the reactions of β-nitrostyrenes with stabilized nucleophiles
  作者：Kuo-Hsi Kao、Cherng-Shi Yang、Ju-Tsung Liu、Wen-Wei Lin、Hui-Yu Fang、Ching-Fa Yao、Kwunmin Chen

  DOI：10.1016/s0040-4020(98)00883-7

  日期：1998.11

  beta-Nitrostyrenes 1 react with various stabilized nucleophiles to generate hydroximoyl chlorides and nitroalkanes after workup with ice cold concentrated hydrochloric acid One-pot synthesis of bicyclic products from the Michael addition of different nucleophiles with beta-nitrostyrenes 1 is reported (C) 1998 Elsevier Science Ltd. Ail rights reserved.
• Duffy Jeffy L., Kurth Mark J., J. Org. Chem, 59 (1994) N 14, S 3783-3785
  作者：Duffy Jeffy L., Kurth Mark J.

  DOI：——

  日期：——
• PADWA, ALBERT;CHIACCHIO, UGO;DEAN, DENNIS C.;SCHOFFSTALL, ALLEN M.;HASSNE+, TETRAHEDRON LETT., 29,(1988) N 33, C. 4169-4172
  作者：PADWA, ALBERT、CHIACCHIO, UGO、DEAN, DENNIS C.、SCHOFFSTALL, ALLEN M.、HASSNE+

  DOI：——

  日期：——
• A Novel Intramolecular Silyl Nitronate Cycloaddition Route to Dihydrofuraldehydes and Dihydropyranaldehydes
  作者：Jetty L. Duffy、Mark J. Kurth

  DOI：10.1021/jo00093a009

  日期：1994.7

  The novel transformation (1 --> 3) of propargylic or homopropargylic nitroethers to dihydrofuraldehydes (n = 0) or dihydropyranaldehydes (n = 1) is reported. The transformation proceeds by a silyl nitronate olefin cycloaddition to an N-[(trimethylsilyl)oxy]isoxazolidine intermediate which, upon acid workup, undergoes desilylation with subsequent elimination of hyponitrous acid to 3.