(2S)-10-Bromo-2-decanol | 128705-95-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S)-10-Bromo-2-decanol
• 英文别名: (2S)-10-Bromodecan-2-ol
• CAS: 128705-95-3
• 化学式: C₁₀H₂₁BrO
• 分子量: 237.18
• InChiKey: KRBQJKLKWQOLLY-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  12
• 可旋转键数：
  8
• 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

反应信息

• 作为反应物：
  描述：

  (2S)-10-Bromo-2-decanol 在 偶氮二异丁腈 、 三正丁基氢锡 、 L-Selectride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 甲苯 为溶剂， 反应 2.0h， 生成 (S)-3-羟基十四烷酸
  参考文献：
  名称：

  Synthesis, Conformational Analysis, and Stereoselective Reduction of 14-Membered Ring 3-Keto Lactones

  摘要：

  The synthesis of 3-oxo-13-tetradecanolide (5) and its 2-methyl and 2,2-dimethyl derivatives 7 and 8 have been carried out. The keto carbonyls in 5, 7, and 8 have been reduced with varying degrees of stereoselectivity. The stereoselectivity of the reduction depends on the counterion with the borohydride reducing agent, but selectivities approaching 100% have been achieved for 5 and 7. The structure of the reduced products were determined by X-ray crystallography and chemical correlation. Heavy reliance on the stereoselectivity in the Frater dianion alkylation was used. The solution conformation of the beta-keto lactones was found to be based on A both from NMR studies and molecular mechanics calculations. However, we are not able to predict the observed stereoselectivity in the hydride reduction of the ketones using this conformation. Thus we suggest the reduction proceeds through conformation B' in which the two carbonyls are chelated to the counterion. The conformations of the resulting alcohols are more complex and have both inter- and intramolecular hydrogen bonding which control the conformations. The use of polar maps to illustrate similarities and differences in conformations is demonstrated. These conformations are used to rationalize the physical and chemical properties of the beta-keto and beta-hydroxy 14-membered lactones.

  DOI：

  10.1021/jo00103a034
• 作为产物：
  描述：

  2-[(7-溴庚基)氧基]四氢-2H-吡喃 在 1,5-cis,cis-cyclooctadiene 、 四溴化碳 、 4-甲基苯磺酸吡啶 、 magnesium 、 1,2-二溴乙烷 、 三苯基膦 、 copper(l) chloride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 21.5h， 生成 (2S)-10-Bromo-2-decanol
  参考文献：
  名称：

  合成von（+）-Aspicilin mit Bausteinen aus nachwachsenden Rohstoffen † ‡ §

  摘要：

  利用可再生资源中的构件合成（+）-阿斯匹林

  DOI：

  10.1002/hlca.19890720813

文献信息

• Synthese von (+)-Aspicilin mit Bausteinen aus nachwachsenden Rohstoffen
  作者：Gerhard Quinkert、Erhard Fernholz、Peter Eckes、Doris Neumann、Gerd Dürner

  DOI：10.1002/hlca.19890720813

  日期：1989.12.13

  Synthesis of (+)-Aspicilin Using Building Blocks from Renewable Resources

  利用可再生资源中的构件合成（+）-阿斯匹林
• QUINKERT, GERHARD;FERNHOLZ, ERHARD;ECKES, PETER;NEUMANN, DORIS;DURNER, GE+, HELV. CHIM. ACTA , 72,(1989) N, C. 1753-1786
  作者：QUINKERT, GERHARD、FERNHOLZ, ERHARD、ECKES, PETER、NEUMANN, DORIS、DURNER, GE+

  DOI：——

  日期：——
• Synthesis, Conformational Analysis, and Stereoselective Reduction of 14-Membered Ring 3-Keto Lactones
  作者：Edward G. Neeland、James P. Ounsworth、Russel J. Sims、Larry Weiler

  DOI：10.1021/jo00103a034

  日期：1994.12

  The synthesis of 3-oxo-13-tetradecanolide (5) and its 2-methyl and 2,2-dimethyl derivatives 7 and 8 have been carried out. The keto carbonyls in 5, 7, and 8 have been reduced with varying degrees of stereoselectivity. The stereoselectivity of the reduction depends on the counterion with the borohydride reducing agent, but selectivities approaching 100% have been achieved for 5 and 7. The structure of the reduced products were determined by X-ray crystallography and chemical correlation. Heavy reliance on the stereoselectivity in the Frater dianion alkylation was used. The solution conformation of the beta-keto lactones was found to be based on A both from NMR studies and molecular mechanics calculations. However, we are not able to predict the observed stereoselectivity in the hydride reduction of the ketones using this conformation. Thus we suggest the reduction proceeds through conformation B' in which the two carbonyls are chelated to the counterion. The conformations of the resulting alcohols are more complex and have both inter- and intramolecular hydrogen bonding which control the conformations. The use of polar maps to illustrate similarities and differences in conformations is demonstrated. These conformations are used to rationalize the physical and chemical properties of the beta-keto and beta-hydroxy 14-membered lactones.