5-butoxy-3-phenyl-4,5-dihydroisoxazole | 50899-19-9

• 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-butoxy-3-phenyl-4,5-dihydroisoxazole
• 英文别名: 5-Butoxy-3-phenyl-4,5-dihydro-1,2-oxazole
• CAS: 50899-19-9
• 化学式: C₁₃H₁₇NO₂
• 分子量: 219.283
• InChiKey: SJLYLYHLAZHQGA-UHFFFAOYSA-N

物化性质

• 沸点：
  125-127 °C(Press: 1 Torr)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  30.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯甲醛 在 三乙烯二胺 、 亚硝酸特丁酯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 5-butoxy-3-phenyl-4,5-dihydroisoxazole
  参考文献：
  名称：

  可见光介导的三组分合成异恶唑啉和异恶唑的策略

  摘要：

  异恶唑啉和异恶唑通常用作许多治疗剂和天然产物的核心结构。然而，在室温下合成这些特殊基序的无金属和无催化策略仍然是一项具有挑战性的任务。在此，我们报告了一种三组分策略，通过在可见光照射下原位形成的硝基化合物和烯烃/炔烃的[3 + 2]环加成提供不同的异恶唑啉和异恶唑。

  DOI：

  10.1021/acs.orglett.4c00671

文献信息

• A Convenient Preparative Method of Nitrile Oxides by the Dehydration of Primary Nitro Compounds with Ethyl Chloroformate or Benzenesulfonyl Chloride in the Presence of Triethylamine
  作者：Tomio Shimizu、Yoshiyuki Hayashi、Hiroshi Shibafuchi、Kazuhiro Teramura

  DOI：10.1246/bcsj.59.2827

  日期：1986.9

  nitrile oxides (MeOCOC≡N→O, PhC≡N→O, and EtC≡N→O) were effectively generated in situ by dehydration of the corresponding primary nitro compounds (RCH2NO2) with PhSO2Cl or ClCOOEt in the presence of triethylamine. Various cycloadducts were prepared by the reaction of them with dipolarophiles. Some advantages of these methods are described in comparison with other known methods.

  在三乙胺的存在下，通过用 PhSO2Cl 或 ClCOOEt 使相应的初级硝基化合物 (RCH2NO2) 脱水，原位有效地生成了三种腈氧化物（MeOCOC≡N→O、PhC≡N→O 和 EtC≡N→O）。各种环加合物是通过它们与偶极试剂反应制备的。与其他已知方法相比，描述了这些方法的一些优点。
• <i>O</i>-Ethoxycarbonyl Hydroximoyl Chloride as Nitrile Oxide Precursor
  作者：Tomio Shimizu、Yoshiyuki Hayashi、Nobuhiro Furukawa、Kazuhiro Teramura

  DOI：10.1246/bcsj.64.318

  日期：1991.1

  O-Ethoxycarbonyl hydroximoyl chloride serves as a stable precursor for nitrile oxide and is converted into the 1,3-dipole when heated under reflux in pyridine.

  O-乙氧羰基羟肟酰氯作为腈氧化物的稳定前体，在吡啶中回流加热时转化为 1,3-偶极子。
• Nitrile Oxide 1,3-Dipolar Cycloaddition by Dehydration of Nitromethane Derivatives Under Continuous Flow Conditions
  作者：Malte Brasholz、Simon Saubern、G. Paul Savage

  DOI：10.1071/ch11079

  日期：——

  Aliphatic nitrile oxides were generated in situ, by dehydration of terminal nitro compounds, and reacted with dipolarophiles using continuous flow techniques to afford substituted isoxazolines. The yields of cycloadducts were comparable with traditional flask-based reactions but reaction times were much shorter. In-line scavenger cartridges conveniently removed by-products and unreacted reagents to give almost pure crude products. The process was demonstrated up to gram scale.

  通过末端硝基化合物的脱水，在原位生成脂肪族腈氧化物，并利用连续流技术与二极性化合物反应，生成取代的异噁唑类化合物。环加载产物的产量与传统的烧瓶反应相当，但反应时间更短。在线清除剂滤筒可方便地清除副产物和未反应试剂，从而得到几乎纯净的粗产品。该工艺已在克级规模上得到验证。
• Generation of nitrite oxides via O-tributylstannyl aldoximes; application to the synthesis of isoxazolines and isoxazoles
  作者：Osamu Moriya、Hideo Takenaka、Masaichi Iyoda、Yoshikiyo Urata、Takeshi Endo

  DOI：10.1039/p19940000413

  日期：——

  hypochlorite and bis(tributyltin) oxide. The reaction proceeded efficiently under mild conditions, in which O-stannylated aldoximes 2 are thought to be key intermediates. This reaction system was applicable to the one-pot syntheses of isoxazole derivatives 4 and 5 in the presence of dipolarophiles via a [3 + 2] cycloaddition.

  亚硝酸盐氧化物易于通过醛肟1与次氯酸叔丁酯和双（三丁基锡）氧化物反应而生成。该反应在温和的条件下有效地进行，在该条件下，O-锡烷基化的醛肟2被认为是关键的中间体。该反应体系适用于在偶极亲和性存在下通过[3 + 2]环加成反应的一锅合成异恶唑衍生物4和5。
• Synthesis of isoxazolines and isoxazoles via generation of nitrile oxides from O-stannyl aldoximes
  作者：Osamu Moriya、Hideo Takenaka、Yoshikiyo Urata、Takeshi Endo

  DOI：10.1039/c39910001671

  日期：——

  The reactions of O-tributylstannyl aldoximes and active halogen compounds such as tert-butyl hypochlorite or N-bromosuccinimide, whereby nitrile oxides are generated effectively, are applied to the preparations of isoxazolines and isoxazoles via[3 + 2] dipolar cycloaddition.

  O-tributylstannyl aldoximes 与活性卤素化合物（如次氯酸叔丁酯或 N-溴琥珀酰亚胺）的反应可有效生成腈氧化物，该反应可用于通过[3 + 2]二极环加成法制备异噁唑和异噁唑。