7-Phenyl-6-heptynal dimethyl acetal | 180572-57-0

• 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: 7-Phenyl-6-heptynal dimethyl acetal
• 英文别名: 7-phenyl-hept-6-ynal-dimethylacetal
• CAS: 180572-57-0
• 化学式: C₁₅H₂₀O₂
• 分子量: 232.323
• InChiKey: ILWZVDATFWQHOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.22
• 重原子数：
  17.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  7-Phenyl-6-heptynal dimethyl acetal 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以90%的产率得到7-phenylhept-6-ynal
  参考文献：
  名称：

  Domino imine condensation/intramolecular polar [4?+ + 2?]-cycloaddition of anilines and ?-unsaturated aldehydes: A versatile tool for the highly diastereoselective synthesis of 1,2,3,4,4a,9,9a,10-octahydroacridines

  摘要：

  The highly diastereoselective synthesis of substituted 1,2,3,4,4a,9,9a,10-octahydroacridines 7, 8 with five stereogenic centers has been achieved by domino imine condensation/intramolecular polar [4 pi(+)+2 pi]-cycloaddition of anilines 3 and omega-unsaturated aldehydes 4. The transformations which can be performed under mild reaction conditions using 0.3 eq. BF3 . Et(2)O as a Lewis acid give the cycloadducts 7, 8 with yields ranging from 63-76%. The relative configuration of 7, 8 was assigned by H-1- and C-13-NMR spectroscopy. For 7a, an X-ray crystal structure analysis was obtained. Experimental as well as semiempirical results support a polar [4 pi(+) + 2 pi]-cycloaddition under kinetic control. It is assumed that the diastereoselectivity of the process is governed by decalin-like exo-E-anti-transition state structures 24, 25 with equatorial arrangement of the bulky substituents R(2).

  DOI：

  10.1002/prac.19963380189
• 作为产物：
  描述：

  5,5-dimethoxypentan-1-ol 在 吡啶 、 正丁基锂 、 lithium bromide 作用下， 以 四氢呋喃 、 正己烷 、 二甲基亚砜 、 丙酮 为溶剂， 反应 18.5h， 生成 7-Phenyl-6-heptynal dimethyl acetal
  参考文献：
  名称：

  Domino imine condensation/intramolecular polar [4?+ + 2?]-cycloaddition of anilines and ?-unsaturated aldehydes: A versatile tool for the highly diastereoselective synthesis of 1,2,3,4,4a,9,9a,10-octahydroacridines

  摘要：

  The highly diastereoselective synthesis of substituted 1,2,3,4,4a,9,9a,10-octahydroacridines 7, 8 with five stereogenic centers has been achieved by domino imine condensation/intramolecular polar [4 pi(+)+2 pi]-cycloaddition of anilines 3 and omega-unsaturated aldehydes 4. The transformations which can be performed under mild reaction conditions using 0.3 eq. BF3 . Et(2)O as a Lewis acid give the cycloadducts 7, 8 with yields ranging from 63-76%. The relative configuration of 7, 8 was assigned by H-1- and C-13-NMR spectroscopy. For 7a, an X-ray crystal structure analysis was obtained. Experimental as well as semiempirical results support a polar [4 pi(+) + 2 pi]-cycloaddition under kinetic control. It is assumed that the diastereoselectivity of the process is governed by decalin-like exo-E-anti-transition state structures 24, 25 with equatorial arrangement of the bulky substituents R(2).

  DOI：

  10.1002/prac.19963380189

文献信息

• Iodotrimethylsilane-induced Cyclization of 6-Alkynal Acetals
  作者：Kazuaki Takami、Hideki Yorimitsu、Hiroshi Shinokubo、Seijiro Matsubara、Koichiro Oshima

  DOI：10.1055/s-2001-10792

  日期：——

  Treatment of 7-phenyl-6-heptynal dimethyl acetal with iodotrimethylsilane afforded 2-(1-iodobenzylidene)cyclohexyl methyl ether via the intramolecular nucleophilic attack of the carbon-carbon triple bond to the oxonium ion generated by the action of iodotrimethylsilane.

  将7-苯基-6-庚炔醛二甲缩醛与碘三甲基硅烷反应，通过碳-碳三键对由碘三甲基硅烷作用生成的氧鎓离子的分子内亲核进攻，得到了2-（1-碘苄叉）环己基甲醚。
• Relay Catalysis for Selective Aerobic Oxidative Esterification of Primary Alcohols with Methanol
  作者：Yibo Yu、Jie Lin、Anni Qin、Huanan Wang、Jie Wang、Weiyi Wang、Guolin Wu、Qian Zhang、Hui Qian、Shengming Ma

  DOI：10.1021/acs.orglett.4c01059

  日期：2024.4.26

  and ubiquitous in polymers, bioactive compounds, and natural products. Their traditional synthetic approach is the esterification of carboxylic acids or their activated derivatives with alcohols. Herein, a bimetallic relay catalytic protocol was developed for the aerobic esterification of one alcohol in the presence of a slowly oxidizing alcohol, which has been identified as methanol. A concise synthesis

  酯是大宗化学品和精细化学品，普遍存在于聚合物、生物活性化合物和天然产品中。他们的传统合成方法是羧酸或其活化衍生物与醇的酯化。在此，开发了一种双金属中继催化方案，用于在缓慢氧化的醇（已被鉴定为甲醇）存在下对一种醇进行有氧酯化。进行了邻苯酸的简明合成以证明该反应的实用性和潜力。