1,7,8-triaza-3,3,6,6-tetramethyl-5-oxa-2-oxo-1-phenylspiro<3,4>oct-7-ene | 134209-90-8

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 1,7,8-triaza-3,3,6,6-tetramethyl-5-oxa-2-oxo-1-phenylspiro<3,4>oct-7-ene
• 英文别名: 1,7,8-triaza-3,3,6,6-tetramethyl-5-oxa-2-oxo-1-phenylspiro[3,4]oct-7-ene；3,3,7,7-tetramethyl-1-phenyl-8-oxa-1,5,6-triazaspiro[3.4]oct-5-en-2-one；3,3,6,6-Tetramethyl-1-phenyl-5-oxa-1,7,8-triazaspiro[3.4]oct-7-en-2-one
• CAS: 134209-90-8
• 化学式: C₁₄H₁₇N₃O₂
• 分子量: 259.308
• InChiKey: ZKCFNTCBRWZZDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  54.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,7,8-triaza-3,3,6,6-tetramethyl-5-oxa-2-oxo-1-phenylspiro<3,4>oct-7-ene 在 对甲苯磺酸 作用下， 以 1,4-二氧六环 、 1,1,2-三氯乙烷 为溶剂， 反应 14.0h， 生成 8-chloro-1-(p-chlorophenyl)-3,3-dimethyl-δ-carboline-2,4-dione
  参考文献：
  名称：

  Interaction of β-Lactam Carbenes with Aryl Isonitriles:  An Unprecedented Rearrangement of 2-Azetidinonylidene Indoles to δ-Carbolinones

  摘要：

  The reaction of, beta-lactam carbenes with aryl isonitriles proceeded in a novel [2 + 2] fashion to give high yields of 2-azetidinonylidene indoles 4, which underwent an unprecedented rearrangement to furnish 4-arylimino-delta-carbolin-2-ones 5 in almost quantitative yields. Acid catalyzed rearrangement and the subsequent hydrolysis of 2-azetidinonylidene indoles 4 produced two types of delta-carbolin-2,4-diones 10 and 11, respectively, in good to excellent yields. The photophysical study showed that both delta-carbolin-2,4-diones 10 and 11 are highly fluorescent with the fluorescent quantum yields being up to 0.43.

  DOI：

  10.1021/jo0700631
• 作为产物：
  描述：

  acetone 4-phenylsemicarbazone 在 lead(IV) acetate 、 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 1,7,8-triaza-3,3,6,6-tetramethyl-5-oxa-2-oxo-1-phenylspiro<3,4>oct-7-ene
  参考文献：
  名称：

  Zoghbi, Michel; Warkentin, John, Canadian Journal of Chemistry, 1993, vol. 71, # 6, p. 912 - 918

  摘要：

  DOI：

文献信息

• The Nucleophilic Addition of β-Lactam Carbenes to Alkylphenylketenes for a Ready Approach to Spiro[β-lactam-2,1′-indene] Derivatives
  作者：Yong-Jia Li、Cai-Xia Yan、Zhong-Xin Sun、Ying Cheng

  DOI：10.1071/ch12046

  日期：——

  The nucleophilic reaction of ambident β-lactam carbenes with alkylphenylketenes is studied, which produces two types of spiro[β-lactam-2,1′-indene] derivatives in total yields of 55–89 %. This work not only provides the first example that ambident carbenes behave with high activity towards ketenes, but also developes the application of β-lactam carbenes in the construction of spiro-β-lactam compounds.

  研究了 Ambident β-内酰胺碳烯与烷基苯甲烯的亲核反应，该反应生成了两种类型的螺[β-内酰胺-2,1′-茚]衍生物，总产率为 55-89%。这项工作不仅首次证明了羰基烯类化合物对酮类化合物具有高活性，而且还开发了β-内酰胺羰基烯类化合物在构建螺-β-内酰胺化合物中的应用。
• The reaction of β-lactam carbenes with 3,6-di(2-pyrimidinyl)tetrazine: regulating products by reaction conditions
  作者：Cai-Xia Yan、Yuan Zhao、Xiao-Rong Wang、Ying Cheng

  DOI：10.1016/j.tet.2013.10.034

  日期：2013.12

  which produced good yields of novel 5-(3-[1,2,3]triazolo[1,5-a]pyrimidinyl)pyrrol-2-ones or pyrrolo[3′,2′:3,4]pyrrolo[1,2-a]pyrimidin-2-ones under heating at 100 °C or 140 °C, respectively. This work provided a highly efficient strategy for the construction of both [1,2,3]triazolo[1,5-a]pyrimidine and pyrrolo[3′,2′:3,4]pyrrolo[1,2-a]pyrimidine ring systems from the same reactants, and extended the

  β内酰胺卡宾与3,6-二（2-嘧啶基）四嗪反应进行了研究，它生产的新颖的良好产率的5-（3- [1,2,3]三唑并[1,5一]嘧啶基）吡咯-2-酮或吡咯并[3'，2'：3,4]吡咯并[1,2一]在，分别为100℃或140℃加热下嘧啶-2-酮。这项工作两者的结构[1,2,3]三唑并[1,5提供一种高效的策略一个吡咯并[1,2：]嘧啶和吡咯并[3,4 3'，2']一个]嘧啶环由相同的反应物组成的环系统，并扩展了β-内酰胺碳烯在复杂杂环的合成中的应用。
• The reaction of β-lactam carbenes with 3,6-dipyridyltetrazines: switch of reaction pathways by 2-pyridyl and 4-pyridyl substituents of tetrazines
  作者：Xiao-Rong Wang、Juan Xing、Cai-Xia Yan、Ying Cheng

  DOI：10.1039/c1ob06595e

  日期：——

  The reactions of β-lactam carbenes with both 3,6-di(2-pyridyl)tetrazine and 3,6-di(4-pyridyl)tetrazine were studied. It was found that β-lactam carbenes reacted with 3,6-di(2-pyridyl)tetrazine to produce 5-triazolo[1,5-a]pyridylpyrrol-2-ones in good yields, while with 3,6-di(4-pyridyl)tetrazine, they afforded pyrido[c]cyclopenta[b]pyrrol-2-ones in moderate yields. Both reactions were proposed to follow cascade mechanisms containing a 3,6a-dipyridylpyrrolo[3,2-c]pyrazol-5-one intermediate. The different pathways of the transformation of pyrrolo[3,2-c]pyrazol-5-ones were switched by the 2- and 4-pyridyl substituents. This work not only provided a simple and efficient strategy for the construction of novel triazolo[1,5-a]pyridine and pyrido[c]cyclopenta[b]pyrrole derivatives, respectively, but also revealed two different thermal transformation patterns of 3H-pyrazole compounds.

  研究了δ-内酰胺碳化物与 3,6-二(2-吡啶基)四嗪和 3,6-二(4-吡啶基)四嗪的反应。研究发现，δ-内酰胺碳化物与 3,6-二(2-吡啶基)四嗪反应生成 5-三唑并[1,5-a]吡啶吡咯-2-酮，收率良好；而与 3,6-二(4-吡啶基)四嗪反应生成吡啶并[c]环戊并[b]吡咯-2-酮，收率中等。这两个反应都被认为遵循了含有 3,6a-二吡啶基吡咯并[3,2-c]吡唑-5-酮中间体的级联机制。吡咯并[3,2-c]吡唑-5-酮的不同转化途径由 2-和 4-吡啶基取代基切换。这项工作不仅为分别构建新型三唑并[1,5-a]吡啶和吡啶并[c]环戊并[b]吡咯衍生物提供了一种简单高效的策略，而且揭示了 3H 吡唑化合物的两种不同热转化模式。
• A Concise Synthesis of Benzo[<i>h</i>]- and Pyrido[3,2-<i>h</i>]-δ-carbolin-2,4-diones from One-Pot Reaction of β-Lactam Carbenes with Naphthyl and Quinolyl Isonitriles
  作者：Ying Cheng、Gao-Feng Shi、Zhi-Mei Kang、Xiao-Ping Jiang

  DOI：10.1055/s-2008-1067243

  日期：2008.9

  The one-pot reaction of β-lactam carbenes with 1-naphthyl or 5-quinolyl isonitriles followed by treatment with aqueous hydrochloride produced benzo[h]-δ-carbolin-2,4-diones or pyrido[3,2-h]-δ-carbolin-2,4-diones, respectively, in moderate yields. The easy availability of β-lactam carbenes and aryl isonitriles, and the simple chemical manipulations render our approach practical in the synthesis of various novel aryl fused δ-carboline derivatives, which are not easily prepared by other synthetic methods.

  β-内酰胺碳烯与1-萘基或5-喹啉基异腈的单锅反应，然后用水合盐酸处理，分别得到苯并[h]-δ-咔啉-2,4-二酮或吡啶并[3,2-h]-δ-咔啉-2,4-二酮，产率中等。β-内酰胺碳烯和芳基异腈易于获得，化学操作也很简单，这使得我们的方法在合成各种新型芳基稠合δ-咔啉衍生物时非常实用，而这些衍生物很难通过其他合成方法制备。
• Reaction of β-Lactam Carbenes with 2-Pyridyl Isonitriles: A One-Pot Synthesis of 2-Carbonyl-3-(pyridylamino)imidazo[1,2-<i>a</i>]pyridines Useful as Fluorescent Probes for Mercury Ion
  作者：Na Shao、Guang-Xian Pang、Cai-Xia Yan、Gao-Feng Shi、Ying Cheng

  DOI：10.1021/jo201273p

  日期：2011.9.16

  The one-pot reaction of beta-lactam carbenes with 2-pyridyl isonitriles followed by an acidic hydrolysis was reported, which produced 2-carbonyl-3-(pyridylamino)imidazo[1,2-a]pyridines in moderate to good yields. Among the resulting novel imidazo[1,2-a]pyridine derivatives, 1-(6-chloro-3-(5-chloropyridin-2-ylamino)imidazo [1,2-a]pyridin-2-yl)-2-ethylbutan-1-one was demonstrated to be an efficient fluorescent probe for mercury ion both in acetonitrile and in buffered aqueous solution.