6-溴-6-庚烯-1-基乙酸酯 | 731773-23-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 6-溴-6-庚烯-1-基乙酸酯
• 英文名称: 6-bromohept-6-enyl acetate
• 英文别名: 7-Acetoxy-2-bromo-heptene
• CAS: 731773-23-2
• 化学式: C₉H₁₅BrO₂
• 分子量: 235.121
• InChiKey: WQVKOTNCLVXWSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2915390090

反应信息

• 作为反应物：
  描述：

  6-溴-6-庚烯-1-基乙酸酯 在 咪唑 、 4-二甲氨基吡啶 、 正丁基锂 、 三氧化硫吡啶 、 potassium carbonate 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 8.75h， 生成 ((2-bromo-14-(dimethylsilyl)tetradeca-1-en-8,13-diyn-7-yl)oxy)(tert-butyl)dimethylsilane
  参考文献：
  名称：

  Metal-Catalyzed Syntheses of Abridged CDE Rings of Rubriflordilactones A and B

  摘要：

  The development of complementary palladium- and cobalt-catalyzed approaches to tricyclic arylsilanes suitable for elaboration into the CDE ring systems of rubriflordilactones A and B is reported. Microwave conditions are required to effect a cobalt-catalyzed triyne cyclotrimerization, which critically depends on the substitution pattern of the triyne termini. Mild conditions to elaborate these arylsilanes to the CDE cores of the natural products are described.

  DOI：

  10.1021/ol303041j
• 作为产物：
  描述：

  3-庚炔-1-醇 在 4-二甲氨基吡啶 、 三溴化硼 、 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 23.0h， 生成 6-溴-6-庚烯-1-基乙酸酯
  参考文献：
  名称：

  Metal-Catalyzed Syntheses of Abridged CDE Rings of Rubriflordilactones A and B

  摘要：

  The development of complementary palladium- and cobalt-catalyzed approaches to tricyclic arylsilanes suitable for elaboration into the CDE ring systems of rubriflordilactones A and B is reported. Microwave conditions are required to effect a cobalt-catalyzed triyne cyclotrimerization, which critically depends on the substitution pattern of the triyne termini. Mild conditions to elaborate these arylsilanes to the CDE cores of the natural products are described.

  DOI：

  10.1021/ol303041j

文献信息

• Total Synthesis of the <i>Schisandraceae</i> Nortriterpenoid Rubriflordilactone A
  作者：Guilhem Chaubet、Shermin S. Goh、Mujahid Mohammad、Birgit Gockel、Marie-Caroline A. Cordonnier、Hannah Baars、Andrew W. Phillips、Edward A. Anderson

  DOI：10.1002/chem.201703229

  日期：2017.10.9

  Full details of the total synthesis of the Schisandraceae nortriterpenoid natural product rubriflordilactone A are reported. Palladium- and cobalt-catalyzed polycyclizations were employed as key strategies to construct the central pentasubstituted arene from bromoendiyne and triyne precursors. This required the independent assembly of two AB ring aldehydes for combination with a common diyne component

  报道了五味子科降三萜类天然产物 rubriflordilactone A 的全合成细节。钯和钴催化的多环化被用作从溴戊二炔和三炔前体构建中心五取代芳烃的关键策略。这需要独立组装两个AB环醛以与共同的二炔组分结合。人们探索了许多模型系统来研究这两种方法，并建立了具有挑战性的苯并吡喃和丁烯内酯环的安装路线。
• Hypervalent iodine-mediated gem-difluorination of vinyl halides enabled by exclusive 1,2-halo migration
  作者：Chenglong Li、Yangzhen Liao、Xuemei Tan、Xiaozu Liu、Peijun Liu、Wen-Xin Lv、Honggen Wang

  DOI：10.1007/s11426-021-9965-9

  日期：2021.6

  β-Difluorinated alkyl halides are of significant value in the modular synthesis of gem-difluorinated molecules. An exclusive 1,2-halo migratory gem-difluorination of vinyl halides with in situ-generated PhIF2·HF is described. This protocol provides a general and practical approach towards a wide variety of β-difluorinated alkyl bromides. Both α- and β-bromoalkyl alkenes are suitable substrates, leading

  β-二氟化烷基卤化物在宝石-二氟化分子的模块合成中具有重要价值。描述了卤化乙烯基卤化物与原位生成的PhIF 2 ·HF的排他性1,2-卤代宝石-二氟化。该协议为各种β-二氟代烷基溴提供了一种通用而实用的方法。α-和β-溴代烷基烯烃都是合适的底物，导致两种不同类型的产物。将该方案扩展至氯乙烯和碘化物也是可行的。该方法的合成多功能性已通过复杂小分子的后期修饰以及β-二氟烷基卤化物进一步转化为有价值的CF 2的方法得到了强调。含化合物。
• Metal-Catalyzed Syntheses of Abridged CDE Rings of Rubriflordilactones A and B
  作者：Shermin S. Goh、Hannah Baars、Birgit Gockel、Edward A. Anderson

  DOI：10.1021/ol303041j

  日期：2012.12.21

  The development of complementary palladium- and cobalt-catalyzed approaches to tricyclic arylsilanes suitable for elaboration into the CDE ring systems of rubriflordilactones A and B is reported. Microwave conditions are required to effect a cobalt-catalyzed triyne cyclotrimerization, which critically depends on the substitution pattern of the triyne termini. Mild conditions to elaborate these arylsilanes to the CDE cores of the natural products are described.