(3S)-3-[(E)-5-bromo-3-methylpent-3-enyl]-2,2-dimethyloxirane | 153541-25-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: (3S)-3-[(E)-5-bromo-3-methylpent-3-enyl]-2,2-dimethyloxirane
• CAS: 153541-25-4
• 化学式: C₁₀H₁₇BrO
• 分子量: 233.148
• InChiKey: QSIYEVLJDXOHMD-ORZBULNSSA-N

物化性质

• 沸点：
  253.1±13.0 °C(Predicted)
• 密度：
  1.208±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (3S)-3-[(E)-5-bromo-3-methylpent-3-enyl]-2,2-dimethyloxirane 在 正丁基锂 、 碘 、 calcium carbonate 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 5.0h， 生成 (2E,6E)-9-((S)-3,3-dimethyloxiran-2-yl)-1-(4-methoxy-2,3-dimethylphenyl)-3,7-dimethylnona-2,6-dien-4-one
  参考文献：
  名称：

  Enantioselective Total Synthesis of (−)-Walsucochin B

  摘要：

  The first enantioselective total synthesis of the structurally unique nortriterpenoid (-)-walsucochin B has been accomplished through the cationic polyolefin cyclization initiated by chiral epoxide. The core framework and the stereocenters in the natural product were all constructed in this step. A site-selective, late-stage free-radical halogenation and Seyferth-Gilbert homologation was adopted to install the acetylene moiety to synthesize the phenylacetylene. The absolute configuration of walsucochin B was confirmed through enantioselective total synthesis.

  DOI：

  10.1021/ol500553x
• 作为产物：
  描述：

  (6S)-6,7-epoxygeraniol 在 三乙胺 、 lithium bromide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 (3S)-3-[(E)-5-bromo-3-methylpent-3-enyl]-2,2-dimethyloxirane
  参考文献：
  名称：

  （3S）-2,3-氧化角鲨烯的短而收敛的对映选择性合成

  摘要：

  描述了由香叶醇，法尼醇和E-1-溴-4-氯-3-甲基-2-丁烯非常有用的（3S）-2,3-氧化角鲨烯的合成方法，该方法利用了乙酸香叶酯和由E-异戊烯基钡试剂介导的两个E-立体特异性烯丙基偶联反应。

  DOI：

  10.1016/s0040-4039(00)61710-0

文献信息

• A short and convergent enantioselective synthesis of (3S)-2,3-oxidosqualene
  作者：E.J. Corey、Mark C. Noe、Shieh Wen-Chung

  DOI：10.1016/s0040-4039(00)61710-0

  日期：1993.9

  A very useful synthesis of (3S)-2,3-oxidosqualene from geraniol, farnesol and E-1-bromo-4-chloro-3-methyl-2-butene is described which makes use of enantioselective and catalytic dihydroxylation of geranyl acetate and two E-stereospecific allylic coupling reactions mediated by E-prenylbarium reagents.

  描述了由香叶醇，法尼醇和E-1-溴-4-氯-3-甲基-2-丁烯非常有用的（3S）-2,3-氧化角鲨烯的合成方法，该方法利用了乙酸香叶酯和由E-异戊烯基钡试剂介导的两个E-立体特异性烯丙基偶联反应。
• Total Synthesis of Antiproliferative Parvifloron F
  作者：Yohei Saito、Masuo Goto、Kyoko Nakagawa-Goto

  DOI：10.1021/acs.orglett.7b03763

  日期：2018.2.2

  first total synthesis of parvifloron F, a bioactive highly oxidized abietane diterpene, was achieved. The abietane skeleton was constructed by Lewis acid promoted cyclization. Preliminary structure–activity relationship correlations were established for the synthetic intermediates against human tumor cell lines. Certain compounds showed unique selective antiproliferative activity against triple-negative

  Parvifloron F是一种具有生物活性的高度氧化的枞树碱二萜，它是第一个完全合成的化合物。通过路易斯酸促进的环化作用构建了abinetane骨架。建立了针对人类肿瘤细胞系的合成中间体的初步构效关系。某些化合物对三阴性乳腺癌显示出独特的选择性抗增殖活性。松果烷环的氧化水平影响选择性。
• Synthesis of a Dicyano Abietane, a Key Intermediate for the Anti-inflammatory Agent TBE-31
  作者：Evans O. Onyango、Liangfeng Fu、Gordon W. Gribble

  DOI：10.1021/ol403289y

  日期：2014.1.3

  The synthesis of dicyano abietane 11, a potential precursor to the biologically active tricyclic bis-cyano enone 6 (TBE-31), was accomplished in eight steps from epoxide 13. The synthesis features a Lewis acid promoted stereoselective cyclization of epoxide 13 to generate the tricyclic ring system 12 in one step.

  从环氧化物13的八个步骤中完成了对生物活性三环双氰基烯酮6（TBE-31）的潜在前体双氰基abietane 11的合成。该合成具有路易斯酸促进的环氧化物13的立体选择性环化以一步生成三环系统12的特征。
• A New Strategy for Stereocontrol of Cation−Olefin Cyclization. The First Chemical Emulation of the A/B-<i>trans</i>-9,10-<i>syn</i>-Folding Pathway of Steroid Biosynthesis from 2,3-Oxidosqualene
  作者：E. J. Corey、Harold B. Wood

  DOI：10.1021/ja9632926

  日期：1996.1.1
• Enantioselective Total Synthesis of (−)-Walsucochin B
  作者：Shiyan Xu、Jixiang Gu、Huilin Li、Donghui Ma、Xingang Xie、Xuegong She

  DOI：10.1021/ol500553x

  日期：2014.4.4

  The first enantioselective total synthesis of the structurally unique nortriterpenoid (-)-walsucochin B has been accomplished through the cationic polyolefin cyclization initiated by chiral epoxide. The core framework and the stereocenters in the natural product were all constructed in this step. A site-selective, late-stage free-radical halogenation and Seyferth-Gilbert homologation was adopted to install the acetylene moiety to synthesize the phenylacetylene. The absolute configuration of walsucochin B was confirmed through enantioselective total synthesis.