cis-2-butyl-3-(trimethylsilylethynyl)oxirane

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: cis-2-butyl-3-(trimethylsilylethynyl)oxirane
• 英文别名: 2-[(2S,3R)-3-butyloxiran-2-yl]ethynyl-trimethylsilane
• 化学式: C₁₁H₂₀OSi
• 分子量: 196.365
• InChiKey: UZYNOXXLZWEHOJ-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.82
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  cis-2-butyl-3-(trimethylsilylethynyl)oxirane 在 三氟化硼乙醚 、 叔丁基氯化镁 作用下， 以 乙醚 为溶剂， 生成 (3RS,4RS)-3-chloro-1-(trimethylsilyl)oct-1-yn-4-ol
  参考文献：
  名称：

  路易斯酸介导的炔丙基环氧化物的开环：1,2-二取代的均炔丙基醇的立体有择合成。

  摘要：

  在BF 3 Et 2 O形环介导的由有机金属亲核试剂开环氧化物炔的给出了在以良好至优异的产率完全区域选择性和立体有择的方式1,2-二取代homopropargylic醇。

  DOI：

  10.1016/s0040-4039(98)01433-6
• 作为产物：
  描述：

  3-溴-1-三甲基硅基-1-丙炔 在 2,2,6,6-tetramethylpiperidinyl-lithium 作用下， 反应 4.0h， 生成 cis-2-butyl-3-(trimethylsilylethynyl)oxirane
  参考文献：
  名称：

  Application of elementoorganic compounds of 15th and 16th Groups in organic synthesis. 100. Reactions of carbonyl compounds with [(trimethylsilyl)propargyl]diisobutyltelluronium bromide mediated by different strong bases: highly regioselective synthesis of (trimethylsilyl)propargyl alcohols and highly stereoselective synthesis of cis-(trimethylsilyl)alkynyl epoxides

  摘要：

  [(Trimethylsilyl)propargyl)]diisobutyltelluronium bromide (1), after being treated with alkyl- or aryllithium reagent, undergoes a lithium-tellurium exchange reaction via an unstable transient tetraorganyltellurium intermediate, and the in situ generated lithium species reacts with carbonyl compounds to give (trimethylsilyl)propargyl alcohols 2 in high yields with high regioselectivity. However, when the telluronium salt 1 was treated with nonnucleophilic bases such as LDA or lithium 2,2,6,6-tetramethylpiperidide, the moderately stabilized silylated telluronium ylide formed. The silylated telluronium ylide reacted with carbonyl compounds to afford (trimethylsilyl) alkynyl epoxides 11 in good to excellent yields with high cis stereoselectivity.

  DOI：

  10.1021/jo00050a042

文献信息

• A New Diastereodivergent Synthesis of 1,2-Disubstituted Homopropargylic Alcohols
  作者：Fabrice Chemla、Nicolas Bernard、Jean Normant

  DOI：10.1002/(sici)1099-0690(199909)1999:9<2067::aid-ejoc2067>3.0.co;2-r

  日期：1999.9

  These Some other syntheses of homopropargylic alcohols havetypes of compounds are generally prepared by two main been also described: the classical homoaldol reaction ofpathways, the corresponding retrosynthetic analyses of chlorocrotylboronates with aldehydes furnishes homoallylicwhich are depicted on Scheme 1. alcohols bearing a chlorine atom on the double bond; thistype of molecule can undergo an

  这些高丙炔醇的一些其他合成通常通过两种主要的化合物制备：途径的经典高醛醇反应，氯代巴豆基硼酸酯与醛的相应逆合成分析提供高烯丙醇，其在方案1中描述。在双链上带有氯原子的醇键; 这种类型的分子可以通过消除盐酸得到高丙炔醇。
• Total Synthesis of the 7,10-Epimer of the Proposed Structure of Amphidinolide N, Part II: Synthesis of C17-C29 Subunit and Completion of the Synthesis
  作者：Koji Ochiai、Sankar Kuppusamy、Yusuke Yasui、Kenji Harada、Nishant R. Gupta、Yohei Takahashi、Takaaki Kubota、Jun'ichi Kobayashi、Yujiro Hayashi

  DOI：10.1002/chem.201504675

  日期：2016.3.1

  The total synthesis of 7,10‐epimer of the proposed structure of amphidinolide N was accomplished. The requisite chiral C17–C29 subunit was assembled stereoselectively via Keck allylation, Shi epoxidation, diastereoselective 1,3‐reduction, and a later oxidative synthesis of the THF framework. The C1–C13 and C17–C29 subunits were successfully coupled using a Enders RAMP “linchpin” as the C14–C16 three

  完成了所提出的两性霉素N结构的7,10-受体的全合成。必需的手性C17–C29亚基通过Keck烯丙基化，Shi环氧化，非对映选择性1,3-还原和后来的THF骨架氧化合成进行立体选择性组装。使用Enders RAMP“ linchpin”作为C14-C16三碳单元成功地偶联了C1-C13和C17-C29亚基，从而控制了C14和C16的手性。在合成的最后阶段，通过Grieco-Nishizawa烯烃反应成功构建了不稳定的烯丙基环氧部分。
• Facile and highly stereoselective synthesis of cis-trimethylsilylethynyl epoxides via a silylated telluronium ylide
  作者：Zhang-Lin Zhou、Yao-Zeng Huang、Li-Lan Shi

  DOI：10.1039/c39920000986

  日期：——

  Diisobutyltelluronium trimethylsilylpropynyl ylide, generated from 3-trimethylsilylprop-2-ynyldiisobutyltelluronium bromide with lithium 2,2,6,6-tetramethylpiperidide (LiTMP), reacts with carbonyl compounds to afford predominately cis-trimethylsilylethynyl epoxides in good to excellent yields.

  由3-三甲基甲硅烷基丙-2-炔基二异丁基碲化溴化锂与2,2,6,6-四甲基哌啶锂（LiTMP）生成的二异丁基碲铝三甲基甲硅烷基丙炔基内酯与羰基化合物反应生成主要为顺式-三甲基甲硅烷基乙炔基环氧化物，收率良好。