naphtho[1,8-de][1,2]oxazine | 271242-85-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: naphtho[1,8-de][1,2]oxazine
• 英文别名: 4-hydroxynaphtho[1,8-de][1,2]oxazine；naphtho[1,8-de][1,2]oxazin-4-ol；naphth[1,8-de][1,2]oxazin-4-ol；2-Oxa-3-azatricyclo[7.3.1.05,13]trideca-1(12),3,5,7,9(13),10-hexaen-6-ol；2-oxa-3-azatricyclo[7.3.1.05,13]trideca-1(12),3,5,7,9(13),10-hexaen-6-ol
• CAS: 271242-85-4
• 化学式: C₁₁H₇NO₂
• 分子量: 185.182
• InChiKey: SNRZXUUNTXHVNU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  naphtho[1,8-de][1,2]oxazine 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以70%的产率得到2,8-dihydroxy-1-naphthonitrile
  参考文献：
  名称：

  一种新型一锅法合成的异构化萘并[1,2 - d ]异恶唑2-氧化物和萘并[1,8- de ] [1,2]恶嗪环系统。同时的情况下ø -和围在萘-cyclisation

  摘要：

  2-羟基-1-萘醛肟1只经历一釜ø -和围-oxidative环化铅（IV）醋酸盐，得到同分异构的萘并[1,2- d ]异恶唑-2-氧化物2和萘并[1,8 -去] [1,2]恶嗪3。两种异构体均使用常见的邻-亚硝基醌甲基化物中间体。

  DOI：

  10.1016/s0040-4039(00)00029-0
• 作为产物：
  描述：

  1-Formamido-2-naphthol 在 碘苯二乙酸 作用下， 以 叔丁醇 为溶剂， 以80%的产率得到naphtho[1,8-de][1,2]oxazine
  参考文献：
  名称：

  Novel Thermal and Microwave-Assisted Facile Route to Naphthalen-2(1H)-ones via an Oxidative Alkoxylation-Ring-Opening Protocol

  摘要：

  Several novel 1,1-disubstituted-8-hydroxynaphthalen-2(1H)-ones have been efficiently synthesized via a two-step sequence from 2-hydroxy-1-naphthaldehyde oxime. The methodology involves oxidative ring closure and alkoxylation to 3a-alkoxynaphtho[1,8-de][1,2]oxazin-4(3aH)-ones, followed by thermal ring-opening. Both thermal and microwave irradiation conditions were used. A novel one-pot reaction of oxime to 8-isopropoxynaphthalene-1,7-diol using microwave irradiation is also reported.

  DOI：

  10.1021/ol9008574

文献信息

• Oxidation of 1-acyl-2-naphthol oximes: peri - and o -cyclisation and spiro cyclodimerisation of naphthoquinone nitrosomethide intermediates
  作者：Paraskevi Supsana、Petros G Tsoungas、André Aubry、Stavroula Skoulika、George Varvounis

  DOI：10.1016/s0040-4020(01)00189-2

  日期：2001.4

  The oxidation of 2-hydroxynaphthaldehyde oxime with lead(IV) acetate (LTA) gave a mixture of naphtho[1,8-de][1,2]oxazine and a spiro dimer. LTA oxidation of 6-bromo (or nitro)-2-hydroxynaphthaldehyde oximes provided only spiro dimers. Similar treatment of (2-hydroxy-1-naphthyl)keto oximes with LTA gave naphtho[1,8-de][1,2]oxazines and benzo[cd]indol-3(1H)-ones. Low temperature oxidation of 1-(2-hy

  用乙酸铅（IV）（LTA）氧化2-羟基萘甲醛肟，得到萘并[1,8- de ] [1,2]恶嗪和螺二聚体的混合物。6-溴（或硝基）-2-羟基萘甲醛肟的LTA氧化仅提供螺二聚体。用LTA类似处理（2-羟基-1-萘基）酮肟得到萘[1,8- de ] [1,2]恶嗪和苯并[ cd ]吲哚-3（1H）-酮。1-（2-羟基-1-萘基）丙烷-1-酮肟的低温氧化制得2-乙基苯并[ cd ]吲哚-3（1 H）-一和1-乙基萘[1,2- d ]异恶唑- 2氧化物。围-和Ø -Naphthoquinone nitrosomethides被援引作为经历中间体周和邻环化和分子间环二聚。
• A novel one-pot synthesis of isomeric naphtho[1,2-d]isoxazole 2-oxide and naphtho[1,8-de][1,2]oxazine ring systems. A case of simultaneous o- and peri-cyclisation in naphthalene
  作者：Paraskevi Supsana、Petros G Tsoungas、George Varvounis

  DOI：10.1016/s0040-4039(00)00029-0

  日期：2000.3

  2-Hydroxy-1-naphthaldehyde oxime 1 undergoes a one-pot o- and peri-oxidative cyclisation with lead(IV) acetate to give the isomeric naphtho[1,2-d]isoxazole 2-oxide 2 and naphtho[1,8-de][1,2]oxazine 3. A common o-nitroso quinonemethide intermediate is invoked for both isomers.

  2-羟基-1-萘醛肟1只经历一釜ø -和围-oxidative环化铅（IV）醋酸盐，得到同分异构的萘并[1,2- d ]异恶唑-2-氧化物2和萘并[1,8 -去] [1,2]恶嗪3。两种异构体均使用常见的邻-亚硝基醌甲基化物中间体。
• The Reactions of 2,8-Dihydroxynaphthaldehyde
  作者：Roger Adams、D. E. Burney

  DOI：10.1021/ja01849a060

  日期：1941.4
• Novel Thermal and Microwave-Assisted Facile Route to Naphthalen-2(1<i>H</i>)-ones via an Oxidative Alkoxylation-Ring-Opening Protocol
  作者：Chrysanthi Dolka、Kristof Van Hecke、Luc Van Meervelt、Petros G. Tsoungas、Erik V. Van der Eycken、George Varvounis

  DOI：10.1021/ol9008574

  日期：2009.7.16

  Several novel 1,1-disubstituted-8-hydroxynaphthalen-2(1H)-ones have been efficiently synthesized via a two-step sequence from 2-hydroxy-1-naphthaldehyde oxime. The methodology involves oxidative ring closure and alkoxylation to 3a-alkoxynaphtho[1,8-de][1,2]oxazin-4(3aH)-ones, followed by thermal ring-opening. Both thermal and microwave irradiation conditions were used. A novel one-pot reaction of oxime to 8-isopropoxynaphthalene-1,7-diol using microwave irradiation is also reported.
• Naphtho[1,8-de][1,2]Oxazin-4-ol: Precursor to 1,2,8-Trisubstituted Naphthalenes and 1-Unsubstituted Naphtho[1,2-d]isoxazole 2-Oxide: A Novel Isomerization of the N-Oxide to Nitrile Oxide en Route to Isoxazol(in)es
  作者：Ioannis E. Gerontitis、Petros G. Tsoungas、George Varvounis

  DOI：10.3390/molecules29010048

  日期：——

  deuterated DMSO at room temperature, was rearranged to its isomer 2-hydroxy-8-methoxy(naphthalen-1-yl)nitrile oxide. The isomerization was detected by time-course plot 1H NMR spectroscopy and further identified from its 13C NMR and HRMS spectra. The nitrile oxide was stable in (non)deuterated DMSO for at least 18 h. A 3,4-bis(2-hydroxy-8-methoxynaphthalen-1-yl)-1,2,5-oxadiazole 2-oxide, as a dimerization product

  萘并[1,8-去][1,2]恶嗪-4-醇及其酰基或苄基衍生物对各种2,8-二羟基-1-萘腈开放，通过（去）保护方案和还原，可以提供目标(E)-2-羟基-8-甲氧基-1-萘醛。将其转化为相应的肟，再用二乙酸苯碘 (III) (PIDA) 氧化邻环化为 9-甲氧基萘并[1,2-d]异恶唑 2-氧化物。后者在室温下在氘代 DMSO 中重排为其异构体 2-羟基-8-甲氧基（萘-1-基）氧化腈。通过时程图 1H NMR 光谱检测异构化，并通过 13C NMR 和 HRMS 光谱进一步鉴定。氧化腈在（非）氘代 DMSO 中稳定至少 18 小时。排除了作为二聚产物的 3,4-双(2-羟基-8-甲氧基萘-1-基)-1,2,5-恶二唑 2-氧化物或作为重排异构体的异氰酸酯，前者通过其 HRMS 谱，后者是其与取代异恶唑的 1,3-偶极环加成反应。