1-(1-Ethoxynon-2-ynyl)benzotriazole | 171815-70-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: 1-(1-Ethoxynon-2-ynyl)benzotriazole
• CAS: 171815-70-6
• 化学式: C₁₇H₂₃N₃O
• 分子量: 285.389
• InChiKey: VKAMRGUPCXAYNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  39.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(1-Ethoxynon-2-ynyl)benzotriazole 在 盐酸 、 正丁基锂 作用下， 以 四氢呋喃 、 环己烷 、 丙酮 为溶剂， 反应 0.4h， 生成 1-(Trimethylsilyl)-2-nonyn-1-one
  参考文献：
  名称：

  Novel and Convenient Routes to Functionalized Alkynyl Ketones from 1-(Benzotriazol-1-yl)propargyl Ethyl Ethers

  摘要：

  1-(Benzotriazol-1-yl)propargyl ethyl ethers, readily accessible from propargyl aldehyde diethyl acetals and benzotriazole, undergo smooth Lithiation at the methine carbon and subsequent reactions with alkyl halides, aldehydes, ketones, imines, esters, trialkylsilyl chlorides, dialkyl carbonates, and isocyanates to yield the corresponding substituted ethers. Hydrolysis of these intermediates under acidic conditions affords a wide variety of alkynyl ketones bearing hydroxy, amino, acyl, trimethylsilyl, alkoxycarbonyl, and (alkylamino)carbonyl substituents at the alpha-position in good to excellent overall yields.

  DOI：

  10.1021/jo00128a038
• 作为产物：
  描述：

  1-辛炔 在 乙基溴化镁 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 10.5h， 生成 1-(1-Ethoxynon-2-ynyl)benzotriazole
  参考文献：
  名称：

  N-杂环碳烯催化的炔基1,2-二酮

  摘要：

  首次通过N杂环卡宾（NHC）催化实现炔基1,2-二酮的酯化反应，从而可以在非常温和的条件下快速获得多种合成和药学上重要的α-吡喃酮。提出了一种全新的NHC催化的mpolung模式，其中包含O-酰化的烯丙基酯作为关键中间体。此外，据推测，以一系列的基团迁移和新的键形成为特征的空前反应路径证明了产物的形成。

  DOI：

  10.1002/adsc.201700700

文献信息

• Novel and Facile Syntheses of Alkenyl, Alkynyl, and Aryl 1,2-Diketones
  作者：Alan R. Katritzky、Zuoquan Wang、Hengyuan Lang、Daming Feng

  DOI：10.1021/jo970092j

  日期：1997.6.13

  Novel and facile routes to alkenyl, alkynyl, and aryl 1,2-diketones utilize treatment of benzotriazole derivatives 1, 7a,b, and 15a-d with butyllithium and subsequent reaction with esters or acid chlorides to yield the substituted intermediates 2a-d, 8a,b, and 16a-g. Reactions of the deprotonated 1 and 7 with alpha,beta-unsaturated aldehydes followed by oxidation also produces similar intermediates 5 and 11a,b. Subsequent hydrolyses of the intermediates of type 2, 5, 8, 11, and 16 afford diverse 1,2-diketones in good yields.
• α-(Benzotriazol-1-YL)Propargyl Ethyl Ethers: Novel Precursors to Enediynes, Enynes and Dienynes
  作者：Alan R. Katritzky、Zhongxing Zhang、Hengyuan Lang

  DOI：10.1080/00397919608003826

  日期：1996.11

  Deprotonated 1-(benzotriazol-1-yl)propargyl ethyl ethers react with propargyl, allyl and alkyl bromides to give the expected substituted derivatives 2, 4 and 9, respectively. Subsequent eliminations of the benzotriazolyl group upon treatment with NaH or ZnBr2, and elaboration of the acetylene group, generate ethoxy substituted enediynes 3, 6, 8, dienynes 7 and enynes 12. Grignard reagents or LiAlH4 convert 9 into a-ethoxy substituted alkynes 10 and 11.
• N-Heterocyclic Carbene-Catalyzed Umpolung of Alkynyl 1,2-Diketones
  作者：Xiangwen Kong、Guoxiang Zhang、Shuang Yang、Xiaozhi Liu、Xinqiang Fang

  DOI：10.1002/adsc.201700700

  日期：2017.8.17

  umpolung of alkynyl 1,2‐diketones via N‐heterocyclic carbene (NHC) catalysis was achieved for the first time, allowing the rapid access to a large variety of synthetically and pharmaceutically important α‐pyrones under very mild conditions. A completely new NHC‐catalyzed umpolung pattern involving an O‐acylated allenolate as the key intermediate was proposed. Moreover, an unprecedented reaction pathway

  首次通过N杂环卡宾（NHC）催化实现炔基1,2-二酮的酯化反应，从而可以在非常温和的条件下快速获得多种合成和药学上重要的α-吡喃酮。提出了一种全新的NHC催化的mpolung模式，其中包含O-酰化的烯丙基酯作为关键中间体。此外，据推测，以一系列的基团迁移和新的键形成为特征的空前反应路径证明了产物的形成。
• Novel and Convenient Routes to Functionalized Alkynyl Ketones from 1-(Benzotriazol-1-yl)propargyl Ethyl Ethers
  作者：Alan R. Katritzky、Hengyuan Lang

  DOI：10.1021/jo00128a038

  日期：1995.11

  1-(Benzotriazol-1-yl)propargyl ethyl ethers, readily accessible from propargyl aldehyde diethyl acetals and benzotriazole, undergo smooth Lithiation at the methine carbon and subsequent reactions with alkyl halides, aldehydes, ketones, imines, esters, trialkylsilyl chlorides, dialkyl carbonates, and isocyanates to yield the corresponding substituted ethers. Hydrolysis of these intermediates under acidic conditions affords a wide variety of alkynyl ketones bearing hydroxy, amino, acyl, trimethylsilyl, alkoxycarbonyl, and (alkylamino)carbonyl substituents at the alpha-position in good to excellent overall yields.