tert-butyl(hex-3-yn-2-yloxy)dimethylsilane | 1198582-40-9

• 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(hex-3-yn-2-yloxy)dimethylsilane
• 英文别名: t-butyl(hex-3-yn-2-yloxy)dimethylsilane；Tert-butyl-hex-3-yn-2-yloxy-dimethylsilane
• CAS: 1198582-40-9
• 化学式: C₁₂H₂₄OSi
• 分子量: 212.407
• InChiKey: GBXXOJCPBDZPHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.81
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  庚醛 、 三异丙基硅烷 、 tert-butyl(hex-3-yn-2-yloxy)dimethylsilane 在 bis(1,5-cyclooctadiene)nickel (0) 、 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene hydrochloride 、 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 以77%的产率得到(E)-7-hexyl-9,9-diisopropyl-2,2,3,3,5,10-hexamethyl-6-propylidene-4,8-dioxa-3,9-disilaundecane
  参考文献：
  名称：

  Cooperativity of Regiochemistry Control Strategies in Reductive Couplings of Propargyl Alcohols and Aldehydes

  摘要：

  The nickel-catalyzed reductive coupling of propargyl alcohols and alkynes proceeds with excellent regiochemical control with an underlying electronic preference that can be supplemented by ligand size effects. The products obtained may be readily converted to substructures that are not directly available by an aldehyde-alkyne reductive coupling. A simple model for how steric and electronic factors are both important in governing regiochemistry in couplings of this type is presented, along with examples of how the effects can combine in either a constructive or destructive manner.

  DOI：

  10.1021/ol902561r
• 作为产物：
  描述：

  3-己炔-2-醇 、 叔丁基二甲基氯硅烷 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以95%的产率得到tert-butyl(hex-3-yn-2-yloxy)dimethylsilane
  参考文献：
  名称：

  Regioselective Catalytic Hydroboration of Propargylic Species Using Cu(I)-NHC Complexes

  摘要：

  The catalytic regioselective hydroboration of propargylic alcohols and ethers was investigated using NHC-CuCl. We observe that different NHC-CuCl complexes catalyze hydroborations of propargylic substrates with opposite regioselectivity. A 6-NHC-CuCl complex provides alpha-selectivity whereas beta-selectivity is achieved using a 5-NHC-CuCl complex. The reaction tolerates a wide range of functional groups.

  DOI：

  10.1021/ol302086v

文献信息

• Cationic Alkynyl Heck Reaction toward Substituted Allenes Using BobCat: A New Hybrid Pd(0)-Catalyst Incorporating a Water-Soluble dba Ligand
  作者：Robynne K. Neff、Doug E. Frantz

  DOI：10.1021/jacs.8b11759

  日期：2018.12.19

  cationic alkynyl Heck reaction between aryl triflates and alkynes to give substituted allenes is described. Key to the success of this method was the discovery and development of a new hybrid Pd(0)-catalyst, BobCat, that incorporates a water-soluble dba-ligand and biaryl phosphine ligand to provide substituted allenes in good yields under mild reaction conditions.

  描述了芳基三氟甲磺酸酯和炔烃之间的阳离子炔基 Heck 反应生成取代的丙二烯。这种方法成功的关键是发现和开发了一种新的混合 Pd(0)-催化剂 BobCat，它结合了水溶性 dba-配体和联芳膦配体，在温和的反应条件下以良好的产率提供取代的丙二烯。