1-溴-2-十五烷酮 | 70243-14-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-溴-2-十五烷酮
• 英文名称: 1-bromo-pentadecan-2-one
• 英文别名: 1-Bromo-2-pentadecanone；1-bromopentadecan-2-one
• CAS: 70243-14-0
• 化学式: C₁₅H₂₉BrO
• 分子量: 305.299
• InChiKey: VQSBLCYXZVPAIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  17
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 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-溴-2-十五烷酮 在 sodium hydroxide 作用下， 以 四氢呋喃 、 硝基甲烷 为溶剂， 生成 2-[(2R,6S)-6-hydroxy-4,4-dimethyl-6-tridecyl-morpholin-4-ium-2-yl]acetic acid
  参考文献：
  名称：

  Acylcarnitine analogues as topical, microbicidal spermicides.

  摘要：

  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.

  DOI：

  10.1016/s0960-894x(99)00423-0
• 作为产物：
  描述：

  1-十五碳烯 在 chromium(VI) oxide 、 N-溴代丁二酰亚胺(NBS) 、 硫酸 、 三氯化铁 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 1-溴-2-十五烷酮
  参考文献：
  名称：

  Acylcarnitine analogues as topical, microbicidal spermicides.

  摘要：

  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.

  DOI：

  10.1016/s0960-894x(99)00423-0

文献信息

• PYROLYSIS OF β-HYDROXY-α-BROMOSULFOXIDES: A SIMPLE SYNTHESIS OF BROMOMETHYL KETONES
  作者：Vichai Reutrakul、Angkana Tiensripojamarn、Kosan Kusamran、Surachai Nimgirawath

  DOI：10.1246/cl.1979.209

  日期：1979.3.5

  The reaction of lithio bromomethyl phenyl sulfoxide with aldehydes gave the corresponding β-hydroxy-α-bromosulfoxides. Pyrolysis of these hydroxysulfoxides yielded the expected bromemethyl ketones in excellent yields.

  硫代溴甲基苯基亚砜与醛反应得到相应的β-羟基-α-溴亚砜。这些羟基亚砜的热解以极好的收率产生了预期的溴甲基酮。
• 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。
• Synthesis of α-halomethyl ketones: Oxidative hydrolysis of vinyl halides
  作者：Howard E. Morton、M.Robert Leanna

  DOI：10.1016/0040-4039(93)88064-p

  日期：1993.7

  Oxidative hydrolysis (e.g. aqueous NBS) of various vinyl halides affords the corresponding alpha-halomethyl ketones in good yield and purity.
• Synthesis and inhibitory activity of difluoroketone substrate analogs of N-myristoyltransferase.
  作者：Karen M. Neder、Stephanie A. French、Stephen P.F. Miller

  DOI：10.1016/s0040-4020(01)89601-0

  日期：1994.1

  Two fluorinated nonhydrolyzable analogs of myristoyl-coenzyme A were synthesized and tested for inhibitory activity against N-myristoyltransferase (NMT). S-(2,2-Difluoro-3-oxohexadecyl)-coenzyme A (3) and S-(3,3-difluoro-2-oxopentadecyl)-coenzyme A (2) were prepared by alkylation of coenzyme A and were purified by reverse phase chromatography. Inhibition of NMT was observed with 3 and 2, with IC50's of 110 nM and 80 nM, respectively, in an in vitro assay developed in our laboratory. The known unfluorinated analog S-(2-oxopentadecyl)-coenzyme A (1) was found to have an IC50 of 7 nM. At 100 mu M in D2O, 3 was 59% hydrated and 2 was 88% hydrated.
• REUTRAKUL VICHAI; TIENSRIPOJAMARN ANGKANA; KUSAMRAN KOSAN; NIMGIRAWATH SU+, CHEM. LETT., 1979, NO 3, 209-212
  作者：REUTRAKUL VICHAI、 TIENSRIPOJAMARN ANGKANA、 KUSAMRAN KOSAN、 NIMGIRAWATH SU+

  DOI：——

  日期：——