12-bromododecan-3-ol | 216753-21-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 12-bromododecan-3-ol
• 英文别名: 12-Bromo-3-dodecanol
• CAS: 216753-21-8
• 化学式: C₁₂H₂₅BrO
• 分子量: 265.234
• InChiKey: QMRIZCCTRUEVGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 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

反应信息

• 作为反应物：
  描述：

  12-bromododecan-3-ol 在 Celite 、 对甲苯磺酸 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 3.0h， 生成 2-(9-bromononyl)-2-ethyl-1,3-dioxolane
  参考文献：
  名称：

  Rhodium-Catalyzed Cyclohydrocarbonylation:  Application to the Synthesis of (+)-Prosopinine and (−)-Deoxoprosophylline

  摘要：

  Efficient convergent total syntheses of (+)-prosopinine (1) and (-)-deoxoprosophylline (4) were accomplished using Rh-BIPHEPHOS complex-catalyzed cyclohydrocarbonylation as the key step. The Rh-BIPHEPHOS complex-catalyzed cyclohydrocarbonylation of I, derived from (R)-serine, at 65 degrees C and 4 atm of CO and H-2 (1:1) in ethanol afforded 6-ethoxypiperidine II, which was transformed to enantiopure (+)-prosopinine (1) in 3 steps. In a similar manner, (-)-deoxoprosophylline was synthesized through cyclohydrocarbonylation of IV derived from (S)-serine, giving 6-ethoxypiperidine V. The key intermediate V was transformed to enantiopure (-)-deoxoprosophylline (4) in 4 steps. These two short total syntheses clearly demonstrate the usefulness of the extremely regioselective cyclohydrocarbonylation process developed in these laboratories for the concise syntheses of piperidine alkaloids and related compounds.

  DOI：

  10.1021/jo9815608
• 作为产物：
  描述：

  10-溴癸醛 、 乙基溴化镁 以 四氢呋喃 为溶剂， 反应 0.5h， 以90%的产率得到12-bromododecan-3-ol
  参考文献：
  名称：

  Rhodium-Catalyzed Cyclohydrocarbonylation:  Application to the Synthesis of (+)-Prosopinine and (−)-Deoxoprosophylline

  摘要：

  Efficient convergent total syntheses of (+)-prosopinine (1) and (-)-deoxoprosophylline (4) were accomplished using Rh-BIPHEPHOS complex-catalyzed cyclohydrocarbonylation as the key step. The Rh-BIPHEPHOS complex-catalyzed cyclohydrocarbonylation of I, derived from (R)-serine, at 65 degrees C and 4 atm of CO and H-2 (1:1) in ethanol afforded 6-ethoxypiperidine II, which was transformed to enantiopure (+)-prosopinine (1) in 3 steps. In a similar manner, (-)-deoxoprosophylline was synthesized through cyclohydrocarbonylation of IV derived from (S)-serine, giving 6-ethoxypiperidine V. The key intermediate V was transformed to enantiopure (-)-deoxoprosophylline (4) in 4 steps. These two short total syntheses clearly demonstrate the usefulness of the extremely regioselective cyclohydrocarbonylation process developed in these laboratories for the concise syntheses of piperidine alkaloids and related compounds.

  DOI：

  10.1021/jo9815608

文献信息

• F18-labeled thia fatty acids and methods of making and using the same
  申请人：Duke University

  公开号：US06362352B1

  公开（公告）日：2002-03-26

  Sulfur heteroatom substitution at the C4 position of 18F-labeled fatty acids yields a tracer that is retained in proportion to the beta-oxidation rates in mammalian tissue, particularly hypoxic myocardium. Most preferably, the invention is embodied in an [18F]fluoro-4-thia-fatty acid having a chain length of between 8 to 20 carbon atoms. The 18F-labeled 4-thia fatty acids of this invention find particular utility the radiolabelling of tissue sites (e.g., myocardium) for purposes of positron emission tomography.

  在18F标记的脂肪酸的C4位置进行硫杂原子替换，可以得到一种示踪剂，其保留与哺乳动物组织中的β-氧化速率成比例，特别是在低氧心肌中。最好的情况下，该发明体现在具有8到20个碳原子链长的[18F]氟-4-硫-脂肪酸中。本发明的18F标记的4-硫脂肪酸在正电子发射断层扫描的组织部位（例如心肌）的放射性标记中具有特殊的实用价值。
• US6362352B1
  申请人：——

  公开号：US6362352B1

  公开（公告）日：2002-03-26
• [EN] F-18-LABELED THIA FATTY ACIDS AND METHODS OF MAKING AND USING THE SAME<br/>[FR] ACIDES GRAS THIA ETIQUETES AU F-18 ET PROCEDES DE FABRICATION ET D'UTILISATION CORRESPONDANTS
  申请人：UNIV DUKE

  公开号：WO2000063216A1

  公开（公告）日：2000-10-26

  Sulfur heteroatom substitution at the C4 position of 18F-labeled fatty acids yields a tracer that is retained in proportion to the beta-oxidation rates in mammalian tissue, particularly hypoxic myocardium. Most preferably, the invention is embodied in an [18F]fluoro-4-thia-fatty acid having a chain length of between 8 to 20 carbon atoms. The 18F-labeled 4-thia fatty acids of this invention find particular utility the radiolabelling of tissue sites (e.g., myocardium) for purposes of positron emission tomography.
• Rhodium-Catalyzed Cyclohydrocarbonylation:  Application to the Synthesis of (+)-Prosopinine and (−)-Deoxoprosophylline
  作者：Iwao Ojima、Ephraim S. Vidal

  DOI：10.1021/jo9815608

  日期：1998.10.1

  Efficient convergent total syntheses of (+)-prosopinine (1) and (-)-deoxoprosophylline (4) were accomplished using Rh-BIPHEPHOS complex-catalyzed cyclohydrocarbonylation as the key step. The Rh-BIPHEPHOS complex-catalyzed cyclohydrocarbonylation of I, derived from (R)-serine, at 65 degrees C and 4 atm of CO and H-2 (1:1) in ethanol afforded 6-ethoxypiperidine II, which was transformed to enantiopure (+)-prosopinine (1) in 3 steps. In a similar manner, (-)-deoxoprosophylline was synthesized through cyclohydrocarbonylation of IV derived from (S)-serine, giving 6-ethoxypiperidine V. The key intermediate V was transformed to enantiopure (-)-deoxoprosophylline (4) in 4 steps. These two short total syntheses clearly demonstrate the usefulness of the extremely regioselective cyclohydrocarbonylation process developed in these laboratories for the concise syntheses of piperidine alkaloids and related compounds.