1-bromo-2-dodecanone | 66130-89-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-bromo-2-dodecanone
• 英文别名: 1-bromododecan-2-one；1-bromododecon-2-one；1-bromo-dodecan-2-one
• CAS: 66130-89-0
• 化学式: C₁₂H₂₃BrO
• 分子量: 263.218
• InChiKey: LPADEKXIYBZPDC-UHFFFAOYSA-N

物化性质

• 熔点：
  42 °C(Solv: methanol (67-56-1))
• 沸点：
  305.3±15.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  14
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 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-2-dodecanone 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-dodecyloxy)-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：

  1-十二烯十二碳烯α-十二碳烯α-十二碳烯 在 氢溴酸 、 氧气 作用下， 以 水 、 乙酸乙酯 为溶剂， 反应 10.0h， 以28%的产率得到1-bromo-2-dodecanone
  参考文献：
  名称：

  使用 I2 或 HBr 水溶液从苯乙烯中轻松有氧光氧化合成苯甲酰碘和溴化物

  摘要：

  我们报告了一种有用的方法，可在水存在下使用 I 2 或 48% HBr 水溶液，通过有氧光氧化从苯乙烯衍生物中轻松合成苯甲酰碘和溴化物。

  DOI：

  10.1055/s-0030-1258022

文献信息

• First Catalyzed Hydration of Halo­alkynes by a Recyclable Catalytic ­System
  作者：Huaxu Zou、Weibao He、Qizhi Dong、Ruijia Wang、Niannian Yi、Jun Jiang、Dongming Pen、Weimin He

  DOI：10.1002/ejoc.201501198

  日期：2016.1

  The hydration of haloalkynes to give α-halomethyl ketones was achieved based on a combination of a Cu(OAc)2 catalyst and a TFA (trifluoroacetic acid) promoter. This is the first synthesis of chloro/bromo/iodo methyl ketones through a hydration reaction catalyzed by a recyclable catalytic system. The catalytic system has a wide substrate scope and excellent chemoselectivity, and the procedure can also

  基于 Cu(OAc)2 催化剂和 TFA（三氟乙酸）促进剂的组合，卤代炔烃水合生成 α-卤代甲基酮。这是首次通过可回收催化系统催化的水合反应合成氯/溴/碘甲基酮。该催化体系具有广泛的底物范围和优异的化学选择性，并且该程序还可以按比例放大。
• Facile Aerobic Photo-Oxidative Synthesis of Phenacyl Iodides and Bromides from Styrenes Using I2 or Aqueous HBr
  作者：Akichika Itoh、Tomoya Nobuta、Shin-ichi Hirashima、Norihiro Tada、Tsuyoshi Miura

  DOI：10.1055/s-0030-1258022

  日期：2010.9

  We report a useful method for facile synthesis of phenacyl iodides and bromides from styrene derivatives by aerobic photo-oxidation using I 2 or 48% aqueous HBr in the presence of water.

  我们报告了一种有用的方法，可在水存在下使用 I 2 或 48% HBr 水溶液，通过有氧光氧化从苯乙烯衍生物中轻松合成苯甲酰碘和溴化物。
• Highly Efficient Synthesis of<i>α</i>-Halomethylketones via Ce(SO₄)₂/Acid Co-Catalyzed Hydration of Alkynes
  作者：Huaxu Zou、Jun Jiang、Niannian Yi、Wenqiang Fu、Wei Deng、Jiannan Xiang

  DOI：10.1002/cjoc.201600417

  日期：2016.12

  A general atom‐economical approach for the synthesis of α‐halomethyl ketones is demonstrated through Ce(SO4)2/acid co‐catalyzed hydration of a wide range of haloalkynes. The reactions are conducted under convenient conditions and provide products with excellent regioselectivity in good to excellent yields, with broad substrate scope. This protocol is an alternative to conventional α‐halogenation of

  通过广泛的卤代炔烃的Ce（SO 4）2 /酸共催化水合作用，证明了一种合成α-卤代甲基酮的一般原子经济方法。反应在便利的条件下进行，并提供具有优异的区域选择性的产物，具有良好的产率至优异的产率，并具有广泛的底物范围。该协议是传统的酮α-卤代反应的替代方法。
• In(OTf) 3 /acid co-catalyzed hydration of 1-haloalkynes to α-halomethyl ketones
  作者：Ming Zeng、Rui-Xue Huang、Wen-Yi Li、Xiao-Wen Liu、Fu-Ling He、Yi-Yuan Zhang、Fang Xiao

  DOI：10.1016/j.tet.2016.04.049

  日期：2016.7

  described. This method provides ready access to α-chloromethyl ketones, α-bromomethyl ketones and α-iodomethyl ketones in moderate to high yields from simple, inexpensive starting materials. A broad substrate scope is achieved, and the reaction is compatible with various functional groups, including alkoxy, trifluoromethyl, halide, hydroxyl, cyclohexyl, and heterocyclic groups.

  描述了新型和有效的In（OTf）3和HOAc协同催化1-卤代炔烃的水合反应。该方法可通过简单，廉价的起始原料以中等到高收率容易地获得α-氯甲基酮，α-溴甲基酮和α-碘甲基酮。获得了广泛的底物范围，并且该反应与各种官能团相容，包括烷氧基，三氟甲基，卤化物，羟基，环己基和杂环基团。
• Electrophilicity of α-oxo gold carbene intermediates: halogen abstractions from halogenated solvents leading to the formation of chloro/bromomethyl ketones
  作者：Weimin He、Longyong Xie、Yingying Xu、Jiannan Xiang、Liming Zhang

  DOI：10.1039/c2ob25235j

  日期：——

  α-Oxo gold carbenes generated via intermolecular oxidation of terminal alkynes are shown to be highly electrophilic and can effectively abstract halogen from halogenated solvents such as 1,2-dichloroethane or 1,2-dibromoethane. Chloro/bromomethyl ketones are prepared in moderate efficiencies in one step using Ph3PAuNTf2 as the catalyst and 8-methylquinoline N-oxide as the oxidant.

  通过端炔的分子间氧化生成的α-氧代金卡宾被证明具有高度的亲电性，并能有效地从卤化溶剂如1,2-二氯乙烷或1,2-二溴乙烷中提取卤素。使用Ph3PAuNTf2作为催化剂和8-甲基喹啉N-氧化物作为氧化剂，一步法中度效率地合成了氯/溴甲基酮。