tert-Butyl-((R)-1-ethynyl-heptyloxy)-dimethyl-silane | 137920-11-7

• 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: tert-Butyl-((R)-1-ethynyl-heptyloxy)-dimethyl-silane
• CAS: 137920-11-7
• 化学式: C₁₅H₃₀OSi
• 分子量: 254.488
• InChiKey: YXBGQHKLSTUEDB-AWEZNQCLSA-N

物化性质

• 沸点：
  273.9±13.0 °C(Predicted)
• 密度：
  0.841±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.98
• 重原子数：
  17.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  tert-Butyl-((R)-1-ethynyl-heptyloxy)-dimethyl-silane 在 正丁基锂 、 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (5R)-undec-3-yn-5-ol
  参考文献：
  名称：

  Synthesis of enantioenriched homopropargylic alcohols through diastereoselective SE' additions of chiral allenylstannanes to aldehydes

  摘要：

  Allenylstannanes (S)-4 and (R)-4, available in ca. 90% ee from alkynones 1 through reduction with the LiAlH4-Darvon alcohol or -ent-Darvon alcohol complex, followed by S(N)2' displacement on the derived mesylates (R)-3 or (S)-3 with Bu3SnLi.CuBr.Me2S, readily add to various aldehydes under Lewis acid catalysis to afford optically active homopropargylic alcohols with good to excellent syn diastereoselectivity. With 2-(benzyloxy)propanal (48), MgBr2-catalyzed reactions are highly stereoselective, affording the syn adduct 49 from the (S)-stannane (S)-4 and the anti adduct 52 from the (R)-stannane (R)-4. BF3-promoted additions give mainly or exclusively the syn adducts 49 and 51. Additions of (S)- and (R)-4 to (R)-3-(benzyloxy)-2-methylpropanal (61) yield the syn adducts 62 and 64 as major or exclusive products.

  DOI：

  10.1021/jo00030a036
• 作为产物：
  描述：

  1-(trimethylsilyl)-1-nonyn-3-one 在 咪唑 、 lithium aluminium tetrahydride 、 (R)-Chirald 、 potassium carbonate 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 tert-Butyl-((R)-1-ethynyl-heptyloxy)-dimethyl-silane
  参考文献：
  名称：

  Synthesis of enantioenriched homopropargylic alcohols through diastereoselective SE' additions of chiral allenylstannanes to aldehydes

  摘要：

  Allenylstannanes (S)-4 and (R)-4, available in ca. 90% ee from alkynones 1 through reduction with the LiAlH4-Darvon alcohol or -ent-Darvon alcohol complex, followed by S(N)2' displacement on the derived mesylates (R)-3 or (S)-3 with Bu3SnLi.CuBr.Me2S, readily add to various aldehydes under Lewis acid catalysis to afford optically active homopropargylic alcohols with good to excellent syn diastereoselectivity. With 2-(benzyloxy)propanal (48), MgBr2-catalyzed reactions are highly stereoselective, affording the syn adduct 49 from the (S)-stannane (S)-4 and the anti adduct 52 from the (R)-stannane (R)-4. BF3-promoted additions give mainly or exclusively the syn adducts 49 and 51. Additions of (S)- and (R)-4 to (R)-3-(benzyloxy)-2-methylpropanal (61) yield the syn adducts 62 and 64 as major or exclusive products.

  DOI：

  10.1021/jo00030a036