9-hexadecyn-8-one | 89319-68-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 9-hexadecyn-8-one
• 英文别名: hexadec-9-yn-8-one
• CAS: 89319-68-6
• 化学式: C₁₆H₂₈O
• 分子量: 236.398
• InChiKey: ICHWPPJIXHKMNF-UHFFFAOYSA-N

物化性质

• 沸点：
  100-102 °C(Press: 0.01 Torr)
• 密度：
  0.865±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  17
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 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：

  9-hexadecyn-8-one 在 一水合肼 作用下， 以 甲醇 为溶剂， 以2.56 g的产率得到5-heptyl-3-hexyl-1H-pyrazole
  参考文献：
  名称：

  Olefin epoxidation in solventless conditions and apolar media catalysed by specialised oxodiperoxomolybdenum complexes

  摘要：

  The epoxidation of olefin substrates, in both apolar organic media and under solventless conditions, with aqueous hydrogen peroxide and catalysed by molybdenum complexes has been investigated. The catalysts compounds employed were the oxodiperoxomolybdenum complexes of several pyridine, 2,2'-bipyridine and pyrazole ligands with apolar functions (alkyl chains, alkyl-trimethylsilyl groups and polydimethylsiloxanyl polymer), which showed enhanced solubility in relatively apolar organic media. Both the isolated complexes and in situ preparations were catalytically active. The solubility of the new catalyst complexes appears to facilitate the catalytic activity in these systems, since activity was not observed for the analogous, insoluble complexes of unfunctionalised ligands. In these systems, the oxidant, aqueous hydrogen peroxide, forms a separate phase and the catalyst resides in the organic phase. From a green chemistry and economic perspective the elimination of organic solvents and co-catalysts from a reaction system would present advantages and, consequently, the epoxidation reaction was also investigated under solventless conditions. The 3-hexyl-5-methylpyrazole and 3-hexyl-5-heptylpyrazole complexes were found to show heightened activities, the latter being particularly efficient in these conditions, whilst bipyridines apparently inhibit the epoxidation. In addition, the mechanism of the epoxidation reaction was studied through DFT calculations for the model olefin substrate ethylene with the oxodiperoxomolybdenum complex of 3-hexyl-5-heptylpyrazole. The oxo-transfer reaction occurred by interaction of the ethylene with the peroxo ligand via the spirocyclic transition state proposed by Sharpless. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2011.02.004
• 作为产物：
  描述：

  9-hexadecyn-8-ol 在 vanadium oxyhexafluoroacetylacetonate 六氟乙酰丙酮 、 3 A molecular sieve 、 氧气 作用下， 以 乙腈 为溶剂， 80.0 ℃ 、101.33 kPa 条件下， 反应 12.0h， 以57%的产率得到9-hexadecyn-8-one
  参考文献：
  名称：

  氧钒络合物催化的炔丙醇的好氧氧化。

  摘要：

  乙腈中由氧乙酰丙酮钒[VO（acac）（2）]和3 A分子筛（MS3A）组成的催化体系可有效地进行丙醇的需氧氧化[R（1）CH（OH）Ctbd1; CR（2）在分子氧的大气压下将其转化为相应的羰基化合物。尽管与R（1）=芳基，烯基和炔基的醇相比，α-炔属烷醇（R（1）=烷基）的反应性较低，但使用VO（hfac）（2）作为催化剂在这些情况下，添加六氟乙酰丙酮可提高产品收率。对于这种氧化，已经提出了涉及钒（V）醇化物和从中消除β-氢的催化循环。

  DOI：

  10.1021/jo025918i

文献信息

• InBr₃-Catalyzed Alkynylation and Allylation of Acid Chlorides: A Facile Synthesis of Alkynyl and Allyl Ketones
  作者：J. S. Yadav、B. V. Reddy、M. Sridhar Reddy、G. Parimala

  DOI：10.1055/s-2003-42438

  日期：——

  Alkynylsilanes and allyltrimethylsilane undergo smooth coupling with acid chlorides in the presence of 5 mol% of indium tribromide under mild conditions to afford the corresponding α,β-acetylenic ketones and β,γ-unsaturated ketones in excellent yields in a short reaction time with high selectivity.

  炔基硅烷和烯丙基三甲基硅烷在温和条件下在 5 mol% 三溴化铟存在下与酰氯平滑偶联，在较短的反应时间内以优异的收率和高选择性得到相应的 α,β-乙炔酮和 β,γ-不饱和酮.
• NOVEL DEORDORISING COMPOSITIONS AND DEODORISING PRODUCTS CONTAINING SAME
  申请人：Casazza André

  公开号：US20120201778A1

  公开（公告）日：2012-08-09

  The invention relates to novel deodorant compositions containing at least one compound of the family of acetylenic ketones and the deodorant products containing them. A particularly preferred composition according to the invention comprises at least one compound of the family of the α-acetylenic ketones and a mixture of aldehydes chosen from two different families.

  本发明涉及一种新型除臭剂组合物，其含有至少一种乙炔酮家族化合物和含有它们的除臭产品。根据本发明，特别优选的组合物包括至少一种α-乙炔酮家族化合物和来自两个不同家族的醛混合物。
• A Simple Synthesis of Alkynyl Ketones via Thexylchloroborane
  作者：Herbert C. Brown、N. G. Bhat、D. Basavaiah

  DOI：10.1055/s-1983-30548

  日期：——
• BROWN, H. C.;BHAT, N. G.;BASAVAIAH, D., SYNTHESIS, BRD, 1983, N 11, 885-886
  作者：BROWN, H. C.、BHAT, N. G.、BASAVAIAH, D.

  DOI：——

  日期：——
• BROWN, H. C.;BHAT, N. G.;BASAVAIAH, D., ISRAEL J. CHEM., 1984, 24, N 2, 72-75
  作者：BROWN, H. C.、BHAT, N. G.、BASAVAIAH, D.

  DOI：——

  日期：——