rac-1-bromododecan-2-ol | 4107-57-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: rac-1-bromododecan-2-ol
• 英文别名: 1-bromo-2-dodecanol；1-bromododecan-2-ol；1-bromo-dodecan-2-ol；1-Brom-dodecanol-(2)；2-Dodecanol, 1-bromo-
• CAS: 4107-57-7
• 化学式: C₁₂H₂₅BrO
• 分子量: 265.234
• InChiKey: QOPILZDHKUVRPM-UHFFFAOYSA-N

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：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 海关编码：
  2905590090

反应信息

• 作为反应物：
  描述：

  rac-1-bromododecan-2-ol 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 以72%的产率得到2-十二烷酮
  参考文献：
  名称：

  Direct conversion of bromohydrins to ketones

  摘要：

  The direct conversion of halohydrins to ketones can be achieved by irradiation in benzene or toluene in the presence of small amounts of p-toluenesulfonic acid. A two step conversion of terminal alkenes to methylketones is thus achieved with good yields and inexpensive reagents.

  DOI：

  10.1016/s0040-4039(00)92214-7
• 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 三氟甲磺酸 、 四丁基溴化铵 、 tetrabutylammonium tetrafluoroborate 、 二甲基亚砜 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.0h， 以57%的产率得到rac-1-bromododecan-2-ol
  参考文献：
  名称：

  Switching the reaction pathways of electrochemically generated β-haloalkoxysulfonium ions – synthesis of halohydrins and epoxides

  摘要：

  β-卤代烷氧基磺鎓离子由电化学生成的Br⁺和I⁺离子与二甲基亚砜（DMSO）稳定后，与氢氧化钠和甲氧基钠反应，分别生成相应的卤水合物和环氧化物，而与三乙胺处理则生成α-卤代羰基化合物。

  DOI：

  10.3762/bjoc.11.27

文献信息

• Switching the reaction pathways of electrochemically generated β-haloalkoxysulfonium ions – synthesis of halohydrins and epoxides
  作者：Akihiro Shimizu、Ryutaro Hayashi、Yosuke Ashikari、Toshiki Nokami、Jun-ichi Yoshida

  DOI：10.3762/bjoc.11.27

  日期：——

  β-Haloalkoxysulfonium ions generated by the reaction of electrogenerated Br⁺ and I⁺ ions stabilized by dimethyl sulfoxide (DMSO) reacted with sodium hydroxide and sodium methoxide to give the corresponding halohydrins and epoxides, respectively, whereas the treatment with triethylamine gave α-halocarbonyl compounds.

  β-卤代烷氧基磺鎓离子由电化学生成的Br⁺和I⁺离子与二甲基亚砜（DMSO）稳定后，与氢氧化钠和甲氧基钠反应，分别生成相应的卤水合物和环氧化物，而与三乙胺处理则生成α-卤代羰基化合物。
• 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。
• Monobromoborane - Dimethyl Sulfide—a Highly Promising Reagent for the Regio- and Chemoselective Brominative Cleavage of Terminal Epoxides into Vicinal Bromohydrins
  作者：Chandra D. Roy、Herbert C. Brown

  DOI：10.1071/ch06408

  日期：——

  Monobromoborane–dimethyl sulfide (BH2Br–SMe2) is a highly regio- and chemoselective reagent useful for the brominative cleavage of the epoxy moiety into bromohydrins in the presence of alkenes, alkynes, ethers, acetals, ketals, and acetonides at 0°C, besides being an excellent hydroborating reagent. Several reactive functional groups, such as chloride, ketones, esters, nitriles, nitros, and thioethers, have been accommodated during such transformations. Although the reduction of acetophenone was completely suppressed at –25°C, 4-chlorobenzaldehyde still underwent 12–13% reduction of an aldehydic group.

  单溴硼烷二甲基硫醚（BH2Br-SMe2）是一种具有高度区域性和化学选择性的试剂，除了是一种出色的氢硼酸化试剂外，还可在 0°C 温度下，在烯、炔、醚、乙缩醛、酮和丙酮的存在下，将环氧分子溴化裂解成溴水酐。在这种转化过程中，可以容纳多种活性官能团，如氯化物、酮、酯、腈、亚硝基和硫醚。虽然苯乙酮的还原反应在零下 25 摄氏度时被完全抑制，但 4-氯苯甲醛仍能还原 12-13% 的醛基。
• Regio- and stereoselective hydroxybromination and dibromination of olefins using ammonium bromide and oxone®
  作者：Arun Kumar Macharla、Rohitha Chozhiyath Nappunni、Narender Nama

  DOI：10.1016/j.tetlet.2012.01.026

  日期：2012.3

  synthesis of vicinal bromohydrins and dibromides from olefins is presented. Various olefins are regio- and stereoselectively hydroxybrominated and dibrominated with anti fashion, following Markonikov’s rule, using eco-friendly, non-toxic, and stable reagents such as NH4Br and oxone® in CH3CN/H2O (1:1) and CH3CN without employing catalyst in moderate to excellent yields. Bromohydrins are formed instantaneously

  提出了从烯烃合成邻位溴代醇和二溴化物的有效方案。各种烯烃是区域选择性和立体选择性hydroxybrominated并用二溴化抗时尚，以下Markonikov的规则，使用环保的，无毒的，和稳定的试剂，例如NH 4 Br和在的冰冷CH 3 CN / H 2 O（1：1 ）和CH 3 CN，而无需使用催化剂即可获得中等至极好的收率。溴代醇立即形成。
• Transformation of Methylene Acetals to Bromoformates with a Combination of Trimethyl(phenylthio)silane and <i>N</i>-Bromosuccinimide
  作者：Tomohiro Maegawa、Misa Nogata、Yuuka Hirose、Shun Ohgami、Akira Nakamura、Yasuyoshi Miki、Hiromichi Fujioka

  DOI：10.1021/acs.joc.7b00776

  日期：2017.7.21

  A novel transformation reaction of methylene acetals, using a combination of trimethyl(phenylthio)silane (PhSTMS) and N-bromosuccinimide (NBS) under mild reaction conditions, is described. Various methylene acetals were converted to their corresponding bromoformates in good to high yields. Under the given conditions, the reaction proceeded via a radical pathway. Further transformation of bromoformates

  描述了在温和的反应条件下，结合使用三甲基（苯硫基）硅烷（PhSTMS）和N-溴代琥珀酰亚胺（NBS）进行的亚甲基缩醛的新型转化反应。将各种亚甲基乙缩醛以良好或高收率转化成其相应的溴甲酸酯。在给定条件下，反应通过自由基途径进行。通过用NaOMe处理，将溴甲酸酯进一步转化为其相应的环氧化物。