pentadeca-6,9-diyn-8-one | 138999-14-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: pentadeca-6,9-diyn-8-one
• 英文别名: Di-heptin-(1)-yl-keton；Pentadeca-6,9-diin-8-on
• CAS: 138999-14-1
• 化学式: C₁₅H₂₂O
• 分子量: 218.339
• InChiKey: MFQDRNUADVEWSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  pentadeca-6,9-diyn-8-one 在 palladium diacetate 、 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 29.0h， 以78%的产率得到(4E,6E,9E,11E)-pentadeca-4,6,9,11-tetraen-8-one
  参考文献：
  名称：

  Stereoselective synthesis of conjugated polyenones from diynones

  摘要：

  (E,E,E,E) - 四烯酮通过钯或钯-铱复合物催化的烯化反应实现立体选择性合成。 (E,E,Z) - 三烯酮通过 ruthenium 复合物催化的烯化反应制备后，随后经 Lindlar 还原法得到。

  DOI：

  10.1016/0040-4039(91)80531-a
• 作为产物：
  描述：

  6,9-pentadecadiyn-8-ol 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 生成 pentadeca-6,9-diyn-8-one
  参考文献：
  名称：

  布朗斯台德酸催化和NIS促进的二炔酮环化：4-吡喃酮，4-吡啶酮和3-吡咯烷酮衍生物的选择性合成

  摘要：

  发现布朗斯台德酸催化的串联环化对于从二炔酮制备一系列多取代的4-吡喃酮非常有效（收率高达99％）。还通过使用NIS和/或布朗斯台德酸选择性地合成了4-吡啶酮和3-吡咯烷酮衍生物。NIS作为亲电子试剂可以在非常温和的反应条件下有效而迅速地促进这些反应。

  DOI：

  10.1021/jo402055a

文献信息

• A Straightforward Synthesis of Ynones by Reaction of Dimethylalkynylaluminum Reagents with Acid Chlorides
  作者：Baomin Wang、Martine Bonin、Laurent Micouin

  DOI：10.1021/jo050760y

  日期：2005.7.1

  Alkynyldimethylaluminum reagents react with various aromatic and aliphatic acid chlorides in a fast and efficient way. This reaction provides a simple entry to numerous ynones, using readily available, inexpensive, and nontoxic metalating agent, and does not require any transition metal as a catalyst.

  炔基二甲基铝试剂可以快速有效地与各种芳香族和脂肪族酰氯反应。该反应使用容易获得，廉价且无毒的金属化剂，可以轻松地进入众多的炔酮，并且不需要任何过渡金属作为催化剂。
• Synthesis of γ-Pyrones and <i>N</i>-Methyl-4-pyridones via the Au Nanoparticle-Catalyzed Cyclization of Skipped Diynones in the Presence of Water or Aqueous Methylamine
  作者：Elisavet-Maria Zantioti-Chatzouda、Vasiliki Kotzabasaki、Manolis Stratakis

  DOI：10.1021/acs.joc.2c00627

  日期：2022.7.1

  were not seen. The reaction does not proceed via the initial 1,3-transposition of the skipped diynones to their corresponding conjugated 1,3-diynone isomers. If aqueous methylamine is added, N-methyl-4-pyridones are exclusively formed in 69–79% yields via an analogous hydroamination/Au-catalyzed 6-endo cyclization pathway.

  负载在 TiO 2上的 Au 纳米颗粒通过三键活化催化跳过的二炔酮在含水二恶烷中水合/6-内环化为 γ-吡喃酮。没有看到可以使用均相离子 Au(I) 催化剂通过竞争且通常占主导地位的 5-外环化途径形成的异构 3(2 H )-呋喃酮。该反应不会通过跳过的二炔酮的初始 1,3-转位为其相应的共轭 1,3-二炔酮异构体进行。如果加入甲胺水溶液，则通过类似的加氢胺化/Au 催化的 6-内环化途径仅以 69-79% 的产率形成N-甲基-4-吡啶酮。
• Forest change monitoring of a remote biosphere reserve
  作者：S. A. Sader、D. J. Hayes、J. A. Hepinstall、M. Coan、C. Soza

  DOI：10.1080/01431160117141

  日期：2001.1

  A forest monitoring framework using Universal Transverse Mercator (UTM) grid cells to report forest change estimates derived from time-series satellite imagery was established for the Maya Biosphere Reserve (MBR) in northern Guatemala. Five dates of Landsat Thematic Mapper imagery were acquired and digitally processed to quantify forest change for four lime periods: 1986 to 1990, 1990 to 1993, 1993 to 1995, and 1995 to 1997. Time-series change estimates are reported for 215 UTM grid cells approximately 100 km(2) each. For the period 1990 to 1997, after the designation of the MBR, the percentage of grid cells with detectable annual forest clearing increased from 38% (1990-93) to 41% (1993-95) and 45% (1995-97). Prior to the establishment of the MBR (1986-90), none of the grid cells exhibited greater than 4.0% annual forest clearing. However in the next three time periods, 7.0%, 8.8% and 9.3% of the grid cells had clearing rates exceeding 4.0% per year. The accuracy of detecting forest clearing was 86.5% over all time periods (Kappa 0.82). Estimates of forest change and user's and producer's accuracy are reported for each time period between 1990 and 1997. The time-series forest change and spatial arrangement of grid locations indicate hot spots where rates and trends of agricultural expansion can be monitored. The baseline survey and the establishment of the UTM grid network to localize forest change estimates provides a framework for future satellite estimates of forest and land cover conversion to be monitored through time. The UTM grid is proposed as the first level in a multi-level ecological monitoring system for the Maya Biosphere Reserve where there are few permanent landmarks in the remote forest region.
• Brønsted Acid Catalyzed and NIS-Promoted Cyclization of Diynones: Selective Synthesis of 4-Pyrone, 4-Pyridone, and 3-Pyrrolone Derivatives
  作者：Yi-Feng Qiu、Fang Yang、Zi-Hang Qiu、Mei-Jin Zhong、Li-Jing Wang、Yu-Ying Ye、Bo Song、Yong-Min Liang

  DOI：10.1021/jo402055a

  日期：2013.12.6

  Brønsted acid catalyzed tandem cyclization was found to be highly effective for the preparation of a series of polysubstituted 4-pyrones from diynones (yield up to 99%). 4-Pyridone and 3-pyrrolone derivatives were also selectively synthesized by employing NIS and/or Brønsted acid. NIS as an electrophilic reagent could promote these reactions efficiently and rapidly under very mild reaction conditions

  发现布朗斯台德酸催化的串联环化对于从二炔酮制备一系列多取代的4-吡喃酮非常有效（收率高达99％）。还通过使用NIS和/或布朗斯台德酸选择性地合成了4-吡啶酮和3-吡咯烷酮衍生物。NIS作为亲电子试剂可以在非常温和的反应条件下有效而迅速地促进这些反应。
• Stereoselective synthesis of conjugated polyenones from diynones
  作者：Cheng Guo、Xiyan Lu

  DOI：10.1016/0040-4039(91)80531-a

  日期：1991.12

  (E,E,E,E) -Tetraenones were stereoselectively synthesized via isomerization of diynones catalyzed by palladium or iridium complexes. (E,E,Z) -Trienones were stereoselectively prepared via isomerization of diynones catalyzed by ruthenium complexes followed by Lindlar hydrogenation.

  (E,E,E,E) - 四烯酮通过钯或钯-铱复合物催化的烯化反应实现立体选择性合成。 (E,E,Z) - 三烯酮通过 ruthenium 复合物催化的烯化反应制备后，随后经 Lindlar 还原法得到。