cis-tert-butyldimethyl((2-phenyltetrahydrofuran-3-yl)ethynyl)silane | 1416256-46-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: cis-tert-butyldimethyl((2-phenyltetrahydrofuran-3-yl)ethynyl)silane
• 英文别名: tert-butyl-dimethyl-[2-[(2R,3R)-2-phenyloxolan-3-yl]ethynyl]silane
• CAS: 1416256-46-6
• 化学式: C₁₈H₂₆OSi
• 分子量: 286.489
• InChiKey: HWXUSYJSNCNWDJ-SJORKVTESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.82
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  cis-tert-butyldimethyl((2-phenyltetrahydrofuran-3-yl)ethynyl)silane 在 硫酸 、 四丁基氟化铵 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 mercury(II) oxide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 44.0h， 生成 1-((2R,3R)-tetrahydro-2-phenylfuran-3-yl)ethanone
  参考文献：
  名称：

  Regioselective Prins Cyclization of Allenylsilanes. Stereoselective Formation of Multisubstituted Heterocyclic Compounds

  摘要：

  The Prins cyclization of hydroxy or amino group-containing allenylsilanes with carbonyl compounds occurred at the allenic terminus in a regio- and stereoselective manner to give the di- or trisubstituted tetrahydrofurans, tetrahydropyrans, and pyrrolidines. During the reaction, the allenic axial chirality of the starting material was efficiently transferred to the newly formed carbon chiral centers of the product.

  DOI：

  10.1021/ol302669q
• 作为产物：
  描述：

  (叔丁基二甲基)乙炔 在 正丁基锂 、 乙酸乙烯酯 、 三氟甲磺酸三甲基硅酯 、 对甲苯磺酸一水合物 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 85.75h， 生成 cis-tert-butyldimethyl((2-phenyltetrahydrofuran-3-yl)ethynyl)silane 、 cis-tert-butyldimethyl((2-phenyltetrahydrofuran-3-yl)ethynyl)silane
  参考文献：
  名称：

  Regioselective Prins Cyclization of Allenylsilanes. Stereoselective Formation of Multisubstituted Heterocyclic Compounds

  摘要：

  The Prins cyclization of hydroxy or amino group-containing allenylsilanes with carbonyl compounds occurred at the allenic terminus in a regio- and stereoselective manner to give the di- or trisubstituted tetrahydrofurans, tetrahydropyrans, and pyrrolidines. During the reaction, the allenic axial chirality of the starting material was efficiently transferred to the newly formed carbon chiral centers of the product.

  DOI：

  10.1021/ol302669q

文献信息

• Regioselective Prins Cyclization of Allenylsilanes. Stereoselective Formation of Multisubstituted Heterocyclic Compounds
  作者：Takuya Okada、Airi Shimoda、Tetsuro Shinada、Kazuhiko Sakaguchi、Yasufumi Ohfune

  DOI：10.1021/ol302669q

  日期：2012.12.21

  The Prins cyclization of hydroxy or amino group-containing allenylsilanes with carbonyl compounds occurred at the allenic terminus in a regio- and stereoselective manner to give the di- or trisubstituted tetrahydrofurans, tetrahydropyrans, and pyrrolidines. During the reaction, the allenic axial chirality of the starting material was efficiently transferred to the newly formed carbon chiral centers of the product.