1-bromo-2-octadecanone | 133794-62-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-bromo-2-octadecanone
• 英文别名: 1-bromoactadecan-2-one；1-bromooctadecan-2-one
• CAS: 133794-62-4
• 化学式: C₁₈H₃₅BrO
• 分子量: 347.379
• InChiKey: ZFZKDGXAVCNASB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  20
• 可旋转键数：
  16
• 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-2-octadecanone 在 盐酸 、 potassium carbonate 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 17.0h， 生成 (R)-5-((R)-1,2-Dihydroxy-ethyl)-4-hydroxy-3-(2-oxo-octadecyloxy)-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：

  十八碳烯 在 sodium bromite 、 溶剂黄146 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以24%的产率得到1-bromo-2-octadecanone
  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

文献信息

• 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。
• Total synthesis of (2S,3S,4R)-plakoridine A
  作者：Dawei Ma、Haiying Sun

  DOI：10.1016/s0040-4039(00)00096-4

  日期：2000.3

  from amine 5 to methyl (E)-2-hexenoate. This ester is converted to the pyrrolidinone 8 via an aldol condensation/deprotection/cyclization. Transformation of the lactam 8 into thiolactam 11 followed by Eschenmoser sulfide contraction provides (2S,3S,4R)-plakoridine A.

  β-氨基酯6是通过将来自胺5的酰胺化锂的非对映选择性迈克尔加成到（E）-2-己酸甲酯而合成的。该酯经由醛醇缩合/脱保护/环化而转化为吡咯烷酮8。将内酰胺8转化为硫内酰胺11，然后进行Eschenmoser硫化物收缩，得到（2 S，3 S，4 R）-哌咯烷A。
• Thermotropic properties of hemicholinium and related lipids
  作者：G. Kumaravel、Ioan I. Negulescu、Richard D. Gandour

  DOI：10.1039/c39930000905

  日期：——

  Cationic morpholine lipids 1 and 6 undergo complex phase transition patterns and exhibit metastable phases; lipids 1,2 and 6 become thermotropic liquid crystals through the first phase transition temperatures, whereas 5 and 7 lose birefringence and become opaque solids.

  阳离子吗啉脂质1和6经历复杂的相变模式并表现出亚稳态；脂质1、2和6在经历第一阶段相变温度后成为热致液晶，而脂质5和7则失去双折射性并变成不透明的固体。
• COMPOUND FOR TREATING CARTILAGE DISORDERS
  申请人：ONO Pharmaceutical Co., Ltd.

  公开号：EP2740724B1

  公开（公告）日：2016-12-28
• NIHRO, YASUNORI;MIYATAKA, HIDEKI;SUDO, TADAMITSU;MATSUMOTO, HITOSHI;SATOH+, J. MED. CHEM., 34,(1991) N, C. 2152-2157
  作者：NIHRO, YASUNORI、MIYATAKA, HIDEKI、SUDO, TADAMITSU、MATSUMOTO, HITOSHI、SATOH+

  DOI：——

  日期：——