十一碳-4-炔-3-酮 | 81113-02-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 十一碳-4-炔-3-酮
• 英文名称: undec-4-yn-3-one
• 英文别名: 4-Undecyn-3-one
• CAS: 81113-02-2
• 化学式: C₁₁H₁₈O
• 分子量: 166.263
• InChiKey: ACWSFNKGFMESBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  十一碳-4-炔-3-酮 在 diethylzinc 、 三乙胺 作用下， 生成 tert-Butyl-dimethyl-((1S,2R)-2-methyl-1-oct-1-ynyl-cyclopropoxy)-silane
  参考文献：
  名称：

  1-（1-炔基）环丙醇通过其六羰基二钴配合物重排为 2-环戊烯酮。炔-Co2(CO)6配合物在有机合成中的新用途

  摘要：

  1-(1-炔基) 环丙醇向 2-环戊烯-1-酮的新重排是在其炔基部分与八羰基二钴 (Co2(CO8)) 络合后进行的。1-(1-炔基) 环丙醇在其炔烃末端具有广泛的取代基，以良好的产率重排为相应的 3-取代的 2-环戊烯-1-酮。In case of the reactions of 1-alkynylcyclopropanols with an alkyl substituent on the cyclopropane ring, either 4-substituted or 5-substituted 2-cyclopenten-1-ones could be selectively obtained by appropriate choice of stereochemistry and protective group of the substrates. 这种重排成功地应用于环戊烯酮环化成环烯烃的反应。根据

  DOI：

  10.1021/ja9734004
• 作为产物：
  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 十一碳-4-炔-3-酮
  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

文献信息

• Cyanotrimethylsilane as a versatile reagent for introducing cyanide functionality
  作者：Kiitiro Utimoto、Yukio Wakabayashi、Takafumi Horiie、Masaharu Inoue、Yuho Shishiyama、Michio Obayashi、Hitosi Nozaki

  DOI：10.1016/s0040-4020(01)88595-1

  日期：1983.1

  Cyanotrimethylsilane adds to some ⇌,β-unsaturated ketones in conjugate manner under the catalytic action of Lewis acids such as triethylaluminium, aluminium chloride, and SnCl2. Hydrolysis of the products gives β-cyano ketones which are identical to the hydrocyanated products of the starting enones. The title silicon reagent reacts with acetals and orthoesters under the catalytic action of SnCI2 or BF3-OEt2

  氰基三甲基硅烷在路易斯酸（如三乙基铝，氯化铝和SnCl 2）的催化作用下以共轭方式加成一些⇌，β-不饱和酮。产物的水解产生与起始烯酮的氢氰化产物相同的β-氰基酮。标题硅试剂在SnCl 2或BF 3 -OEt 2的催化作用下与乙缩醛和原酸酯反应，得到2-烷氧基-和2,2-二烷氧基烷基-腈。将反应应用于O-保护的β-D-呋喃呋喃糖酶，以优异的产率选择性地产生β-d-呋喃呋喃糖基氰化物。
• Iridium-catalyzed [2+2+2] cycloaddition of α,ω-diynes with alkynyl ketones and alkynyl esters
  作者：Toru Hashimoto、Arisa Okabe、Takeshi Mizuno、Mao Izawa、Ryo Takeuchi

  DOI：10.1016/j.tet.2014.09.038

  日期：2014.11

  We found that the combination of [Ir(cod)Cl]2 and rac-BINAP served as an efficient catalyst for the [2+2+2] cycloaddition of 2,7-nonadiyne derivatives and related compounds with alkynyl ketones and alkynyl esters. The corresponding products were obtained in high yields under mild reaction conditions.

  我们发现[Ir（cod）Cl] 2和rac -BINAP的组合可作为有效的催化剂，用于2,7-壬二炔衍生物和相关化合物与炔基酮和炔基酯的[2 + 2 + 2]环加成。在温和的反应条件下，以高收率获得了相应的产物。
• General Synthesis of α-Alkyl Ynones from Morpholine Amides and 1-Copper(I) Alkynes Promoted by Triflic Anhydride
  作者：Yunxiang Weng、Lin Min、Xiaobao Zeng、Lidong Shan、Xinyan Wang、Yuefei Hu

  DOI：10.1021/acs.orglett.0c02944

  日期：2020.11.6

  The first general method for the synthesis of α-alkyl ynones was developed based on the strategy of electrophilic activation of amides. Its distinctive advantages are attributed to the use of air-stable “bare” 1-copper(I) alkyne as a mild nucleophile without any exogeneous ligand.

  基于酰胺的亲电活化策略，开发了第一种合成α-烷基炔酮的通用方法。它的独特优势归因于使用空气稳定的“裸” 1-铜（I）炔烃作为温和的亲核试剂，没有任何外源性配体。
• Improved highly efficient synthesis of α,β-acetylenic ketones. Nature of the intermediate from the reaction of lithium acetylide with boron trifluoride etherate
  作者：Herbert C. Brown、Uday S. Racherla、Shankar M. Singh、Richard B. Wetherill

  DOI：10.1016/s0040-4039(01)81192-8

  日期：1984.1

  A wide variety of α,β-acetylenic ketones were synthesized in very high yields via an exceptionally facile intermolecular reaction of lithium alkynyltrifluoroborates and carboxylic acid anhydrides.

  多种α，β-炔酮的在非常高的产率合成了通过锂alkynyltrifluoroborates和羧酸酐的一个非常容易分子间反应。
• Palladium-catalyzed synthesis of pyrroles
  作者：Kiitiro Utimoto、Hiroshi Miwa、Hitosi Nozaki

  DOI：10.1016/s0040-4039(01)82932-4

  日期：1981.1