(E)-6,6-dimethyl-3-oxo-1-phenyl-1-hepten-4-yne | 905946-25-0

• 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: (E)-6,6-dimethyl-3-oxo-1-phenyl-1-hepten-4-yne
• 英文别名: (E)-6,6-dimethyl-1-phenylhept-1-en-4-yn-3-one；(e)-6,6-Dimethyl-3-oxo-1-phenyl-1-hepten-4-yne
• CAS: 905946-25-0
• 化学式: C₁₅H₁₆O
• 分子量: 212.291
• InChiKey: FVFMDWNPDDGRFD-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  (E)-6,6-dimethyl-3-oxo-1-phenyl-1-hepten-4-yne 在 sodium hydrogensulfide 作用下， 以 乙二醇甲醚 为溶剂， 反应 16.0h， 以85%的产率得到6-tert-butyl-2,3-dihydro-2-phenylthiopyran-4-one
  参考文献：
  名称：

  Synthesis of 2,3-Dihydrothiopyran-4-ones from 3-Oxo-1-pentene-4-ynes

  摘要：

  3-Oxo-1-pentene-4-ynes were converted with sodium sulfide or hydrogensulfide to give 2,6-disubstituted 2,3-dihydrothiopyran-4-one derivatives. The starting materials were prepared in two steps from terminal alkynes and alpha,beta-unsaturated aldehydes.

  DOI：

  10.1007/s00706-006-0571-4
• 作为产物：
  描述：

  3,3-二甲基-1-丁炔 在 manganese(IV) oxide 、 正丁基锂 作用下， 以 四氢呋喃 、 二氯甲烷 、 正戊烷 为溶剂， 生成 (E)-6,6-dimethyl-3-oxo-1-phenyl-1-hepten-4-yne
  参考文献：
  名称：

  Synthesis of unsymmetrically 2,6-disubstituted 2,3-dihydrothiopyran-4-ones

  摘要：

  A series of 2,3-dihydrothiopyran-4-one derivatives with unequal substituents in the 2- and 6-position have been prepared by double conjugate addition of sulfide to enynones. These starting materials were accessed in two steps from terminal alkynes and alpha,beta-unsaturated aldehydes. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.05.080

文献信息

• A General Synthesis of Cross-Conjugated Enynones through Pd Catalyzed Sonogashira Coupling with Triazine Esters
  作者：Dezhi Lin、Yunfang Liu、Hongyu Yang、Xiao Zhang、Huaming Sun、Yajun Jian、Weiqiang Zhang、Jianming Yang、Ziwei Gao

  DOI：10.3390/molecules28114364

  日期：——

  susceptibility of the unsaturated C-C bonds adjacent to the carbonyl group toward Pd catalysts makes the direct conversion of α, β-unsaturated derivatives as acyl electrophiles to cross-conjugated ketones rare. This work presents a highly selective C-O activation approach to prepare cross-conjugated enynones using α, β-unsaturated triazine esters as acyl electrophiles. Under base and phosphine ligand-free

  钯催化的 α, β-不饱和酸衍生物的 Sonogashira 偶联为交叉共轭烯酮提供了一种面向多样性的合成策略。然而，与羰基相邻的不饱和CC键对Pd催化剂的敏感性使得α，β-不饱和衍生物作为酰基亲电子试剂直接转化为交叉共轭酮很少见。这项工作提出了一种高选择性的 CO 活化方法，使用 α, β-不饱和三嗪酯作为酰基亲电子试剂制备交叉共轭烯酮。在无碱和膦配体的条件下，NHC-Pd(II)-烯丙基预催化剂单独有效催化 α, β-不饱和三嗪酯与末端炔烃的交叉偶联，产生 31 个具有不同官能团的交叉共轭烯酮。
• Synthesis of unsymmetrically 2,6-disubstituted 2,3-dihydrothiopyran-4-ones
  作者：Anna Rosiak、Jens Christoffers

  DOI：10.1016/j.tetlet.2006.05.080

  日期：2006.7

  A series of 2,3-dihydrothiopyran-4-one derivatives with unequal substituents in the 2- and 6-position have been prepared by double conjugate addition of sulfide to enynones. These starting materials were accessed in two steps from terminal alkynes and alpha,beta-unsaturated aldehydes. (c) 2006 Elsevier Ltd. All rights reserved.
• Cinchona Alkaloid-Catalyzed Asymmetric Trifluoromethylation of Alkynyl Ketones with Trimethylsilyl Trifluoromethane
  作者：Hiroyuki Kawai、Kentaro Tachi、Etsuko Tokunaga、Motoo Shiro、Norio Shibata

  DOI：10.1021/ol102189c

  日期：2010.11.19

  The first catalytic enantioselective trifluoromethylation of alkynyl ketones 1 with (trifluoromethyl)trimethylsilane is disclosed by an operationally simple procedure, based on the combination of ammonium bromide of bis-cinchona alkaloids with Me4NF to afford trifluoromethyl-substituted tertiary propargyl alcohols (up to 96% ee), which are the important chiral building blocks for pharmaceuticals. Biologically attractive aryl heteroaryl trifluoromethyl carbinols were also synthesized.
• Synthesis of 2,3-Dihydrothiopyran-4-ones from 3-Oxo-1-pentene-4-ynes
  作者：Anna Rosiak、Ralf M. Müller、Jens Christoffers

  DOI：10.1007/s00706-006-0571-4

  日期：2007.1

  3-Oxo-1-pentene-4-ynes were converted with sodium sulfide or hydrogensulfide to give 2,6-disubstituted 2,3-dihydrothiopyran-4-one derivatives. The starting materials were prepared in two steps from terminal alkynes and alpha,beta-unsaturated aldehydes.