1-溴-2-六癸酮 | 21436-52-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-溴-2-六癸酮
• 中文别名: 1-溴-2-六癸酮,97；1-溴-2-十六酮
• 英文名称: 1-bromo-2-hexadecanone
• 英文别名: 1-bromohexadecan-2-one；1-bromo-hexadecan-2-one
• CAS: 21436-52-2
• 化学式: C₁₆H₃₁BrO
• 分子量: 319.326
• InChiKey: ICZYLTOWIBJLIK-UHFFFAOYSA-N

物化性质

• 熔点：
  54-59℃

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  18
• 可旋转键数：
  14
• 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

安全信息

• 海关编码：
  2914700090

反应信息

• 作为反应物：
  描述：

  1-溴-2-六癸酮 在 盐酸 、 碳酸氢钠 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 2.0h， 生成 (R)-5-((S)-1,2-Dihydroxy-ethyl)-3-hydroxy-4-(2-oxo-hexadecyloxy)-5H-furan-2-one
  参考文献：
  名称：

  3-O-Alkylascorbic acids as free-radical quenchers: synthesis and inhibitory effect on lipid peroxidation

  摘要：

  A novel series of 3-O-alkylascorbic acids (3-RASA, 3a-n) was synthesized to act as radical scavengers for active oxygen species and free radicals, and their redox potentials and inhibitory effects on lipid peroxidation in rat liver microsomes were evaluated. The redox potentials of the 3-RASA compounds were increased by the substituent group to 90-190 mV above the potential for ascorbic acid (i.e., 3-RASA compounds were harder to oxidize). Although 3-O-dodecylascorbic acid (3c) and 3-O-(decylcarbomethyl)ascorbic acid (3i) differed in their redox potentials, they both markedly inhibited lipid peroxidation in rat liver microsomes to a similar extent (IC50 = 3.1 and 3.3 x 10(-6) M, respectively). Structure-activity relationship studies demonstrated that the anti lipid peroxidation activity of the 3-RASA compounds was markedly dependent upon their hydrophobicity.

  DOI：

  10.1021/jm00111a034
• 作为产物：
  描述：

  十六碳烯 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-2-六癸酮
  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

• α-Trifluoromethylseleno-substituted ketones synthesis via copper-mediated trifluoromethylselenolation of α-bromoketones
  作者：Yue Yang、Xia Lin、Zhiwei Zheng、Ganglu Lin、Yunxiao Zhang、Yi You、Zhiqiang Weng

  DOI：10.1016/j.jfluchem.2017.10.001

  日期：2017.12

  the report on the synthesis of α-trifluoromethylseleno-substituted ketone derivatives via copper-mediated trifluoromethylselenolation of α-bromoketones with [(bpy)Cu(SeCF3)]2 1. A broad range of substituted 2-bromoacetophenone substrates were found to react smoothly with 1 in the presence of 3 equiv of K3PO4 to afford the corresponding α-trifluoromethylseleno-substituted ketones in good yields. A wide

  在这里，我们公开了通过[（bpy）Cu（SeCF 3）] 2 1通过铜介导的α-溴代酮的三氟甲基硒化反应合成α-三氟甲基硒代酮衍生物的报告。发现了广泛的取代2-溴苯乙酮底物在3当量的K 3 PO 4的存在下，与1平滑反应，以高收率得到相应的α-三氟甲基硒代取代的酮。各种各样的官能团被很好地耐受，并且反应条件适合扩大规模。
• An Improved Protocol for the Synthesis of α-Trifluoromethylthio-Substituted Ketones by Copper-Mediated Trifluoromethylthiolation of α-Bromo Ketones
  作者：Yangjie Huang、Xing He、Haohong Li、Zhiqiang Weng

  DOI：10.1002/ejoc.201403221

  日期：2014.11

  An efficient and practical approach to α-trifluoromethylthio-substituted ketones was developed. The trifluoromethylthiolation of (bpy)Cu(SCF3) (bpy = 2,2′-bipyridyl) with various α-bromo ketones afforded the desired α-trifluoromethylthio-substituted ketones in good yields. The reaction tolerates more functionally than previously reported methods and demonstrates efficient scalability and practicality

  开发了一种有效且实用的 α-三氟甲硫基取代酮方法。(bpy)Cu(SCF3)（bpy = 2,2'-联吡啶）与各种 α-溴酮的三氟甲硫基化以良好的产率提供了所需的 α-三氟甲硫基取代的酮。该反应比以前报道的方法在功能上具有更多的耐受性，并证明了有效的可扩展性和实用性。
• Facile one-pot synthesis of α-bromoketones from olefins using bromide/bromate couple as a nonhazardous brominating agent
  作者：Rajendra D. Patil、Girdhar Joshi、Subbarayappa Adimurthy、Brindaban C. Ranu

  DOI：10.1016/j.tetlet.2009.03.047

  日期：2009.5

  A new method for the preparation of α-bromoketones from olefins using bromide/bromate couple as a nonhazardous brominating agent has been developed. Several α-bromoketones were successfully prepared from a variety of olefins by this method. This procedure is an alternative to conventional molecular bromine.

  已开发出一种使用溴化物/溴酸盐对作为无害溴化剂，由烯烃制备α-溴代酮的新方法。通过这种方法成功地由多种烯烃制备了几种α-溴代酮。该方法是常规分子溴的替代方法。
• New Access to Trisubstituted 3-Pyrrolines under Phosphine Catalysis
  作者：Marie Schuler、Deepti Duvvuru、Pascal Retailleau、Jean-François Betzer、Angela Marinetti

  DOI：10.1021/ol901758k

  日期：2009.10.1

  properly activated by electron-withdrawing groups on both ends, are shown to be suitable substrates for phosphine-promoted organocatalytic processes. Their reactions with imines, under phosphine catalysis, afford a new and efficient synthetic approach to functionalized 3-pyrrolines.

  已显示出通过两端的吸电子基团适当活化的共轭二烯是磷化氢促进的有机催化过程的合适底物。在膦催化下，它们与亚胺的反应为功能化的3-吡咯啉提供了一种新的有效合成方法。
• Rapid and General Access to α-Haloketones Using Quaternary Ammonium Salts as Halogen Sources
  作者：Nan Wu、Mengfei Jiang、Ashley Cao、Lei Huang、Xiumei Bo、Zhou Xu

  DOI：10.1021/acs.joc.3c02195

  日期：2023.12.15

  A general, rapid, and scalable method for the preparation of α-halogenated ketones using N-alkenoxypyridinium salts as substrates and quaternary ammonium salts as halogen sources was developed, featuring mild reaction conditions, excellent functional group tolerance, short reaction times, and a wide substrate scope.

  开发了一种以N-烯氧基吡啶鎓盐为底物、季铵盐为卤素源制备α-卤代酮的通用、快速、可规模化的方法，具有反应条件温和、官能团耐受性优异、反应时间短、适用范围广等特点。底物范围。