1-bromo-heptadecan-2-one | 119293-61-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-bromo-heptadecan-2-one
• 英文别名: 1-bromo-2-heptadecanone；1-Bromoheptadecan-2-one
• CAS: 119293-61-7
• 化学式: C₁₇H₃₃BrO
• 分子量: 333.352
• InChiKey: BSNVQNSCLVHCKO-UHFFFAOYSA-N

物化性质

• 熔点：
  66.3-66.7 °C
• 沸点：
  384.1±15.0 °C(Predicted)
• 密度：
  1.043±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  19
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.94
• 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：

  1-bromo-heptadecan-2-one 在 sodium hydroxide 作用下， 以 硝基甲烷 为溶剂， 反应 17.0h， 生成 Z 15
  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：

  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

文献信息

• Synthesis and Antibiofilm Activity of a Second-Generation Reverse-Amide Oroidin Library: A Structure-Activity Relationship Study
  作者：T. Eric Ballard、Justin J. Richards、Amanda L. Wolfe、Christian Melander

  DOI：10.1002/chem.200801419

  日期：——

  A second-generation library of 2-aminoimidazole-based derivatives incorporating a "reversed amide" (RA) motif in comparison to the marine natural product oroidin were synthesized and subsequently assayed for antibiofilm activity against the medically relevant Gram-negative proteobacteria P. aeruginosa and A. baumannii. Most notably, an in-depth activity profile is reported for the most active subclass

  合成了第二代基于2-氨基咪唑的衍生物，与海洋天然产物oroidin相比，该衍生物结合了“反向酰胺”（RA）主题，随后针对医学上相关的革兰氏阴性菌铜绿假单胞菌和铜绿假单胞菌鲍曼不动杆菌 最值得注意的是，据报道，活性最高的衍生物亚类具有更深的活性，这些亚类的酰胺键上带有线性脂族链。另外，核心模板的进一步结构修饰，例如酰胺键的去除或三唑等排物的取代，导致发现了具有抗生物膜活性的类似物，其对铜绿假单胞菌和铜绿假单胞菌的抑制和分散特性各不相同。鲍曼生物膜。
• ZHAO, CHEN;CHEN, SHAO-LIN;WU, PEI-QIANG;WEN, ZHONG, XUASYUEH SYUEHBAO, 46,(1988) N 8, S. 784-790
  作者：ZHAO, CHEN、CHEN, SHAO-LIN、WU, PEI-QIANG、WEN, ZHONG

  DOI：——

  日期：——
• Acylcarnitine analogues as topical, microbicidal spermicides.
  作者：Prashant S. Savle、Gustavo F. Doncel、Stephen D. Bryant、M. Patricia Hubieki、R. Graham Robinette、Richard D. Gandour

  DOI：10.1016/s0960-894x(99)00423-0

  日期：1999.9

  Acylcarnitine analogues, (+)-6-Carboxylatomethyl-2-alkyl-4,4-dimethylmorpholinium (Z-n, where n = the number of carbons in the alkyl chain), synthesized in multi-gram quantities show in vitro activities as spermicides, anti-HIV agents, and inhibitors of the growth of Candida albicans. Activity improves with increasing chain length. Compound Z-15 is a candidate for further study as a topical, microbicidal spermicide. (C) 1999 Elsevier Science Ltd. All rights reserved.
• (+)-Hemipalmitoylcarnitinium strongly inhibits carnitine palmitoyltransferase-I in intact mitochondria
  作者：Richard D. Gandour、On Tai Leung、Anthony T. Greway、Rona R. Ramsay、Noirin Nic A Bhaird、Frank R. Fronczek、Bret M. Bellard、G. Kumaravel

  DOI：10.1021/jm00054a007

  日期：1993.1

  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.