(2R)-5-[tert-butyl(dimethyl)silyl]oxypent-3-yn-2-ol | 133910-77-7

• 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: (2R)-5-[tert-butyl(dimethyl)silyl]oxypent-3-yn-2-ol
• CAS: 133910-77-7
• 化学式: C₁₁H₂₂O₂Si
• 分子量: 214.38
• InChiKey: FODSMWMDEAMAPC-SNVBAGLBSA-N

物化性质

• 沸点：
  252.9±20.0 °C(Predicted)
• 密度：
  0.918±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.39
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R)-5-[tert-butyl(dimethyl)silyl]oxypent-3-yn-2-ol 、 甲基磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 Methanesulfonic acid (R)-4-(tert-butyl-dimethyl-silanyloxy)-1-methyl-but-2-ynyl ester
  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：

  5-<(tert-butyldimethylsilyl)oxy>-3-pentyn-2-one 在 lithium aluminium tetrahydride 作用下， 生成 (2R)-5-[tert-butyl(dimethyl)silyl]oxypent-3-yn-2-ol
  参考文献：
  名称：

  Highly diastereoselective SE' additions of enantioenriched allenylstannanes to (S)-2-(benzyloxy)propanal

  摘要：

  The BF3-promoted addition of (S)-allenylstannane (S)-6 to aldehyde 16 afforded a 68:32 mixture of diastereomeric homopropargylic alcohols 17 and 18 whereas MgBr2-promoted addition gave adduct 17 as the exclusive product. The (R)-allenylstannane (R)-6, on the other hand, yielded a 30:1 mixture of syn and anti alcohol adducts 19 and 20 with BF3.OEt2 and a 1:92 mixture favoring the anti adduct 20 under MgBr2 catalysis.

  DOI：

  10.1021/jo00010a007

文献信息

• Synthesis of enantioenriched homopropargylic alcohols through diastereoselective SE' additions of chiral allenylstannanes to aldehydes
  作者：James A. Marshall、Xiao Jun Wang

  DOI：10.1021/jo00030a036

  日期：1992.2

  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.
• Highly diastereoselective SE' additions of enantioenriched allenylstannanes to (S)-2-(benzyloxy)propanal
  作者：James A. Marshall、Xiao Jun Wang

  DOI：10.1021/jo00010a007

  日期：1991.5

  The BF3-promoted addition of (S)-allenylstannane (S)-6 to aldehyde 16 afforded a 68:32 mixture of diastereomeric homopropargylic alcohols 17 and 18 whereas MgBr2-promoted addition gave adduct 17 as the exclusive product. The (R)-allenylstannane (R)-6, on the other hand, yielded a 30:1 mixture of syn and anti alcohol adducts 19 and 20 with BF3.OEt2 and a 1:92 mixture favoring the anti adduct 20 under MgBr2 catalysis.