1-diazo-2-heptadecanone | 51865-45-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-diazo-2-heptadecanone
• 英文别名: 1-diazoheptadecan-2-one
• CAS: 51865-45-3
• 化学式: C₁₇H₃₂N₂O
• 分子量: 280.454
• InChiKey: JMTKDBURRARGBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  20
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  19.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-diazo-2-heptadecanone 在 氢溴酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 0.08h， 以92%的产率得到1-bromo-heptadecan-2-one
  参考文献：
  名称：

  (+)-Hemipalmitoylcarnitinium strongly inhibits carnitine palmitoyltransferase-I in intact mitochondria

  摘要：

  The reaction of the methyl ester of (R)-norcarnitine with 1-bromo-2-heptadecanone produces (+)-6-[(methoxycarbonyl)methyl]-2-pentadecyl-4,4-dimethylmorpholinium bromide, 3, which hydrolyzes to (+)-6-(carboxylatomethyl)-2-pentadecyl-4,4-dimethylmorpholinium (hemipalmitoylcarnitinium, HPC) upon treatment with aqueous sodium hydroxide. Single-crystal X-ray analyses have confirmed the structures of (+)-HPC and 3. (+)-HPC inhibits carnitine palmitoyltransferase (CPT-I) activity for the forward reaction (palmitoyl-CoA + carnitine -->) in intact mitochondria from rat heart and rat liver. (+)-HPC competitively (versus carnitine) inhibits CPT-I activity in both rat heart and liver mitochondria with K(i) = 2.8 +/- 0.5 and 4.2 +/- 0.7 muM, respectively. As one of the strongest specific inhibitors of CPT-I, HPC is a potential therapeutic agent in myocardial ischemia and Type II diabetes.

  DOI：

  10.1021/jm00054a007
• 作为产物：
  描述：

  重氮甲烷 、 棕榈酰氯 以 乙醚 为溶剂， 反应 1.5h， 以93%的产率得到1-diazo-2-heptadecanone
  参考文献：
  名称：

  Sigmatropic重排作为氨基酸和肽修饰的工具：烯丙基硫醚重排在制备新糖缀合物和其他缀合物中的应用

  摘要：

  由硒代半胱氨酸连接产生的S-烯丙基半胱氨酸衍生物与稳定和不稳定的铑类胡萝卜素的反应，可使各种功能附着于半胱氨酸残基上。该反应成功地用于引入脂质样残基，氟代烷基链以及单糖和二糖。

  DOI：

  10.1021/jo061439y

文献信息

• Homologation of carboxylic acids by arndt-eistert reaction under ultrasonic waves
  作者：Jean-Yves Winum、Merhnaz Kamal、Alain Leydet、Jean-Pierre Roque、Jean-Louis Montero

  DOI：10.1016/0040-4039(96)00130-x

  日期：1996.3

  The use of ultrasonic activation in the Arndt-Eistert reaction leads rapidly, in good yields, to the expected compounds at room temperature.

  在Arndt-Eistert反应中使用超声活化，可以快速，高收率地在室温下产生预期的化合物。
• An efficient PEG-400 mediated catalyst free green synthesis of 2-amino-thiazoles from α-diazoketones and thiourea
  作者：B HARI BABU、K VIJAY、K BALA MURALI KRISHNA、N SHARMILA、M BABY RAMANA

  DOI：10.1007/s12039-016-1130-0

  日期：2016.9

  A simple and efficient method has been developed for the synthesis of 2-aminothiazoles from α-diazoketones using PEG-400 solvent system. This novel synthetic approach involves the reaction between thiourea and α-diazoketones in PEG-400 at 100 °C to yield the corresponding 2-aminothiazoles in good yields. The method is simple, rapid and generates thiazole derivatives in excellent yields without the

  已经开发出一种简单有效的方法，可以使用PEG-400溶剂系统从α-重氮酮合成2-氨基噻唑。这种新颖的合成方法涉及硫脲与PEG-400中的α-重氮酮在100°C下反应，以高收率产生相应的2-氨基噻唑。该方法简单，快速并且无需使用任何催化剂即可以优异的产率生成噻唑衍生物。该绿色方案可用于以良好收率快速合成各种2-氨基噻唑。 据报道由PEG-400介导，无催化剂，由α-重氮酮和硫脲合成绿色的2-氨基噻唑。
• First Example of Cu(OTf)₂-catalyzed Synthesis of Quinoxalines from α-Diazoketones and Aryl 1,2-Diamines
  作者：J. S. Yadav、B. V. Subba Reddy、Y. Gopala Rao、A. V. Narsaiah

  DOI：10.1246/cl.2008.348

  日期：2008.3.5

  α-Diazoketones undergo smooth coupling with aryl 1,2-diamines in the presence of 10 mol % of copper(II) triflate to provide the corresponding 2-alkyl- or 2-aryl-quinoxalines in excellent yields wit...

  α-重氮酮在 10 mol% 三氟甲磺酸铜 (II) 存在下与芳基 1,2-二胺进行平滑偶联，以优异的收率提供相应的 2-烷基-或 2-芳基-喹喔啉...
• Photochemistry of reactive surface-active compounds in adsorbed monolayers
  作者：David A. Holden、Joseph W. Taylor、Diane Clausen

  DOI：10.1016/s0040-4020(01)90279-0

  日期：1987.1

  1-diazo-2-oxoheptadecane, for example, the products of these two reactions are heptadecanoic acid and a surface-grafted long-chain ester. The latter can be removed as methyl heptadecanoate by ester exchange using methanolic HCl. Pronounced differences were observed between alumina, silica gel and fumed silica as supports, and were attributed to differences in the amount of adsorbed H2O and in the density of surface

  研究了长链重氮酮与叠氮化物在无机固体上吸附的单分子层中的反应，并将其与空气-水界面中单分子层中的相应行为进行了比较。分离出的产物表明，光化学生成的中间体与共吸附水和固体表面的羟基均发生反应。例如，在1-重氮-2-氧杂十七烷的情况下，这两个反应的产物是十七烷酸和表面接枝的长链酯。后者可以通过使用甲醇的HCl进行酯交换而以十六烷酸甲酯的形式除去。在氧化铝，硅胶和气相二氧化硅作为载体之间观察到明显的差异，这归因于H 2吸附量的差异并在表面形成羟基密度的羟基。
• Generation and Rearrangements of Ylides from Tertiary Amines and α-Diazo Ketones − Very High Catalytic Activity of [RuCl(η5-C5H5)(PPh3)2]
  作者：Alessandro Del Zotto、Walter Baratta、Francesca Miani、Giancarlo Verardo、Pierluigi Rigo

  DOI：10.1002/1099-0690(200011)2000:22<3731::aid-ejoc3731>3.0.co;2-9

  日期：2000.11

  The reaction of N,N-dimethyl-2-propen-1-amine, N,N-dimethylbenzylamine and N,N-dimethyl-2-propyn-1-amine with the alpha -diazo ketones N2CHCOR [R = Me (2a), Et (2b), nPr (2c), iPr (2d), (CH2)(10)Me (2e), (CH2)(14)Me (2f) or Ph (2g)] in a 1:1 molar ratio, catalysed by the complex [RuCl(eta (5)-C5H5)(PPh3)(2)] (1) (1% mel), have been investigated. Noticeably, the corresponding alpha -amino ketones 3a-g, 4a-g and 5a-g are readily and quantitatively formed by rearrangement of transient nitrogen ylides. Compounds 3-5, most of which have not yet been reported, have been isolated and fully characterised by IR, H-1 and C-13 NMR spectroscopy and GC-MS. It has been proved that complex 1 is an excellent and specific catalyst for the generation of nitrogen ylides from diazo carbonyls.