3-[2-(1,3-dioxan-2-yl)ethyl]cyclohex-2-en-1-one | 130520-30-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-[2-(1,3-dioxan-2-yl)ethyl]cyclohex-2-en-1-one
• 英文别名: 3-[2-(1,3-Dioxan-2-yl)ethyl]-2-cyclohexen-1-one
• CAS: 130520-30-8
• 化学式: C₁₂H₁₈O₃
• 分子量: 210.273
• InChiKey: MTGLDOJTRBOBSW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[2-(1,3-dioxan-2-yl)ethyl]cyclohex-2-en-1-one 在 N,N-二甲基丙烯基脲 、 sodium hydroxide 、 双氧水 、 potassium hydride 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 42.5h， 生成 3-<2-(1,3-Dioxan-2-yl)ethyl>-2-(phenyloxy)-2-cyclohexen-1-one
  参考文献：
  名称：

  Intramolecular addition reactions of carbonyl ylides formed during photocyclization of aryl vinyl ethers

  摘要：

  Photocyclization of aryl vinyl ethers reportedly proceeds via carbonyl ylide intermediates. The photochemical behavior of several aryl vinyl ethers, which incorporate a pendant alkene side chain, was explored. Naphthyl vinyl ethers 1c and 1d provided products that are consistent with photocyclization and subsequent intramolecular ylide-alkene addition. Product distribution is influenced by solvent and temperature effects. Thus, irradiation of 1c in toluene provides 9a in 87% yield. However, irradiation of 1c in methanol/toluene (1:1) provides 3c (45%), 11 (24%), and 12 (23%). Product 12 results from photoinitiated intramolecular [2 + 2] cycloaddition of the butenoate ester side chain to the naphthalene system.

  DOI：

  10.1021/jo00019a020
• 作为产物：
  描述：

  3-溴环己-2-烯-1-酮 、 (1,3-dioxan-2-yl)ethylmagnesium bromide 在 二甲基硫 、 copper(I) bromide 作用下， 以77%的产率得到3-[2-(1,3-dioxan-2-yl)ethyl]cyclohex-2-en-1-one
  参考文献：
  名称：

  光引发的分子内yyl-烯烃环加成反应

  摘要：

  研究了光瞬态物质的分子内烯烃加成反应。掺入丁烯酸乙酯官能团的芳基乙烯基硫醚的光解提供了类似烯的产物和/或（3 + 2）加合物。产物的形成受结构特征和反应条件的支配。

  DOI：

  10.1016/s0040-4039(00)97478-1

文献信息

• Copper-Catalyzed Asymmetric Conjugate Addition of Trialkylaluminium Reagents to Trisubstituted Enones: Construction of Chiral Quaternary Centers
  作者：Magali Vuagnoux-d'Augustin、Alexandre Alexakis

  DOI：10.1002/chem.200701001

  日期：2007.11.26

  vinylalane species undergo enantioselective conjugate addition to a wide range of 2- or 3-substituted enones (cyclopent-2-enones, cyclohex-2-enones, 3-methyl cyclohept-2-enone) in the presence of catalytic amount of copper salt (copper thiophene carboxylate, [Cu(CH3CN)4]BF4 or [CuOTf]2C6H6) and tropos-phosphoramidite-based ligand. Thus, chiral quaternary centers can be built, with up to 98% ee after rigorous

  在催化作用下，Me3Al，Et3Al和乙烯基丙烷类物质进行对映选择性共轭加成，生成各种2-或3-取代的烯酮（环戊-2-烯酮，环己-2-烯酮，3-甲基环庚-2-烯酮）铜盐（噻吩羧酸铜，[Cu（CH3CN）4] BF4或[CuOTf] 2C6H6）和基于对位亚磷酰胺的配体。因此，经过严格优化实验条件后，可以建立具有高达98％ee的手性四元中心。结果表明，主要的重要参数是试剂引入的顺序。然后，将生成的对映体富集的烯醇铝和手性共轭加合物官能化并用于随后的反应。
• Synthesis of <i>N</i>-substituted quaternary carbon centers through KO<i>t</i>-Bu-catalyzed aza-Michael addition of pyrazoles to cyclic enones
  作者：Subin Yoon、Sungbin Lee、Seung Hyun Nam、Hyejeong Lee、Yunmi Lee

  DOI：10.1039/d2ob01634f

  日期：——

  This study reports an efficient and mild method for the synthesis of cyclic β-amino ketones containing N-substituted quaternary carbon centers via the KOt-Bu-catalyzed aza-Michael addition reaction of pyrazoles to β-substituted cyclic α,β-enones. The amination was promoted by KOt-Bu (3 mol%) at ambient temperature and a wide range of new and versatile β-pyrazolyl ketones were obtained in good yields

  本研究报告了一种高效且温和的方法，通过KO t -Bu 催化的吡唑与β-取代的环状α、β-烯酮的氮杂-迈克尔加成反应，合成含有N-取代季碳中心的环状β-氨基酮。在环境温度下通过 KO t -Bu (3 mol%)促进胺化，并以良好的产率获得了范围广泛的新型多功能β-吡唑基酮。此外，KO t -Bu 催化的环状二烯酮与吡唑的一锅二聚反应通过还探索了 aza-1,6-共轭加法，然后是 aza-1,4-共轭加法。
• Enantioselective Copper-Catalyzed Conjugate Addition to Trisubstituted Cyclohexenones: Construction of Stereogenic Quaternary Centers
  作者：Magali d?Augustin、La�ticia Palais、Alexandre Alexakis

  DOI：10.1002/anie.200462137

  日期：2005.2.18
• DITTAMI, JAMES P.;NIE, XIAO-YI;BUNTEL, CHRISTOPHER J.;RIGATTI, STEVEN, TETRAHEDRON. LETT., 31,(1990) N7, C. 3821-3824
  作者：DITTAMI, JAMES P.、NIE, XIAO-YI、BUNTEL, CHRISTOPHER J.、RIGATTI, STEVEN

  DOI：——

  日期：——
• Photoinitiated intramolecular ylide-alkene cycloaddition reactions
  作者：James P. Dittami、Nie Xiao-Yi、Christopher J. Buntel、Steven Rigatti

  DOI：10.1016/s0040-4039(00)97478-1

  日期：1990.1

  The intramolecular olefin addition reactions of phototransient species were investigated. Photolysis of aryl vinyl sulfides which incorporate the ethyl butenoate functional group provide ene-like products and or (3+2) adducts. Product formation is governed by both structural features and reaction conditions.

  研究了光瞬态物质的分子内烯烃加成反应。掺入丁烯酸乙酯官能团的芳基乙烯基硫醚的光解提供了类似烯的产物和/或（3 + 2）加合物。产物的形成受结构特征和反应条件的支配。