1,9-bis(tert-butyldimethylsilyl)nona-1,8-diyn-5-ol | 1207670-14-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,9-bis(tert-butyldimethylsilyl)nona-1,8-diyn-5-ol
• CAS: 1207670-14-1
• 化学式: C₂₁H₄₀OSi₂
• 分子量: 364.719
• InChiKey: LGBKAQGVESTLCB-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  1,9-bis(tert-butyldimethylsilyl)nona-1,8-diyn-5-ol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以93%的产率得到1,9-bis(tert-butyldimethylsilyl)nona-1,8-diyn-5-one
  参考文献：
  名称：

  Mild and Efficient Desymmetrization of Diynes via Hydroamination: Application to the Synthesis of (±)-Monomorine I

  摘要：

  An efficient silver-catalyzed desymmetrization of amino diynes via hydroamination is reported. A variety of functionalized I-pyrroline derivatives were synthesized in 73% to 88% isolated yields (>98% by H-1 NMR in some cases). The usefulness of this mild hydroamination method was further shown by the desymmetrization of unprotected tert-hydroxy diynes. Structures of two transition states have been studied computationally. An application of this method was demonstrated by a short and efficient synthesis of (+/-)-monomorine I.

  DOI：

  10.1021/jo902674j
• 作为产物：
  描述：

  (4-bromobut-1-ynyl)(tert-butyl)dimethylsilane 、 甲酸乙酯 在 碘 、 magnesium 、 水 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以74%的产率得到1,9-bis(tert-butyldimethylsilyl)nona-1,8-diyn-5-ol
  参考文献：
  名称：

  Mild and Efficient Desymmetrization of Diynes via Hydroamination: Application to the Synthesis of (±)-Monomorine I

  摘要：

  An efficient silver-catalyzed desymmetrization of amino diynes via hydroamination is reported. A variety of functionalized I-pyrroline derivatives were synthesized in 73% to 88% isolated yields (>98% by H-1 NMR in some cases). The usefulness of this mild hydroamination method was further shown by the desymmetrization of unprotected tert-hydroxy diynes. Structures of two transition states have been studied computationally. An application of this method was demonstrated by a short and efficient synthesis of (+/-)-monomorine I.

  DOI：

  10.1021/jo902674j