(5-bromopent-4-ynyloxy)triisopropylsilane | 184370-66-9

• 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: (5-bromopent-4-ynyloxy)triisopropylsilane
• 英文别名: 5-Bromopent-4-ynoxy-tri(propan-2-yl)silane
• CAS: 184370-66-9
• 化学式: C₁₄H₂₇BrOSi
• 分子量: 319.357
• InChiKey: QQFOCYUKNZTBBM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.31
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  N-Boc-苯胺 、 (5-bromopent-4-ynyloxy)triisopropylsilane 在 potassium phosphate 、 1,10-菲罗啉 、 copper(ll) sulfate pentahydrate 作用下， 以 甲苯 为溶剂， 反应 45.0h， 以88%的产率得到phenyl-(5-triisopropylsilanyloxy-pent-1-ynyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of Functionalized Oxazolones by a Sequence of Cu(II)- and Au(I)-Catalyzed Transformations

  摘要：

  A study concerning a two-step sequence leading to the formation of diversely 1,5-disubstituted oxazolones is described. The mild conditions employed allow the efficient and rapid synthesis of a variety of such compounds via an initial Cu(II)-catalyzed coupling of a bromoalkyne with a secondary tert-butyloxycarbamate followed by a Au(I)-catalyzed cycloisomerization of the N-alkynyl tert-butyloxycarbamates thus obtained.

  DOI：

  10.1021/ol703077g
• 作为产物：
  描述：

  1-((triisopropylsilyl)oxy)-4-pentyne 在 N-溴代丁二酰亚胺(NBS) 、 silver nitrate 作用下， 以 丙酮 为溶剂， 生成 (5-bromopent-4-ynyloxy)triisopropylsilane
  参考文献：
  名称：

  Palladium-catalysed hydrostannylations of 1-bromoalkynes. A practical synthesis of (E)-1-stannylalk-1-enes

  摘要：

  重点介绍了一种包含多种氧和氮官能团的(E)-1-锡烷基-1-烯的实用合成方法，涉及1-溴炔的氢锡化反应，随后通过钯催化的碳-溴键断裂反应。

  DOI：

  10.1039/p19960002417

文献信息

• Enantioconvergent Reductive C(sp)−C(sp ³ ) Cross‐Coupling to Access Chiral α‐Alkynyl Phosphonates Under Dual Nickel/Photoredox Catalysis
  作者：Hepan Wang、Xiaoqiang Wu、Tao XU

  DOI：10.1002/anie.202218299

  日期：——

  carbon-carbon bond formation to forge phosphonates with an α-chiral carbon center through C(sp3)−C(sp3) and C(sp2)−C(sp3) couplings has been successful. However, the enantioselective C(sp)−C(sp3) coupling has not yet been disclosed. Reported herein is an unprecedented enantioconvergent cross-coupling of alkynyl bromides and α-bromo phosphonates to deliver chiral α-alkynyl phosphonates.

  过渡金属催化的不对称碳-碳键形成通过 C(sp 3 )−C(sp 3 ) 和 C(sp 2 )−C(sp 3 ) 偶联形成具有 α-手性碳中心的膦酸酯已取得成功。然而，尚未公开对映选择性C(sp)-C(sp 3 )偶联。本文报道了炔基溴化物和 α-溴膦酸酯前所未有的对映收敛交叉偶联，以提供手性 α-炔基膦酸酯。
• Designed Bifunctional Phosphine Ligand-Enabled Gold-Catalyzed Isomerizations of Ynamides and Allenamides: Stereoselective and Regioselective Formation of 1-Amido-1,3-dienes
  作者：Xingguang Li、Zhixun Wang、Xu Ma、Pei-nian Liu、Liming Zhang

  DOI：10.1021/acs.orglett.7b02624

  日期：2017.11.3

  By using designed biphenyl-2-ylphosphines functionalized with a remote basic groups as ligands, N-alkynyl-o-nosylamides are directly converted to (1E,3E)-1-amido-1,3-dienes with excellent diastereoselectivities under gold catalysis. With allenamides as substrates, the gold-catalyzed isomerizations are high yielding and applicable to a broad substrate scope including various nitrogen protecting groups and exhibit unprecedented (3E)-selectivities for the distal C-C double bond and good regioselectivities. Combining this gold catalysis with one-pot Diels-Alder reactions leads to rapid assembly of valuable bicyclic compounds.
• Palladium-catalysed hydrostannylations of 1-bromoalkynes. A practical synthesis of (E)-1-stannylalk-1-enes
  作者：Christopher D. J. Boden、Gerald Pattenden、Tao Ye

  DOI：10.1039/p19960002417

  日期：——

  A practical synthesis of (E)-1-stannylalk-1-enes containing a range of oxygen and nitrogen functionality is highlighted, involving hydrostannylation followed by palladium-catalysed carbon–bromine bond cleavage reactions of 1-bromoalkynes.

  重点介绍了一种包含多种氧和氮官能团的(E)-1-锡烷基-1-烯的实用合成方法，涉及1-溴炔的氢锡化反应，随后通过钯催化的碳-溴键断裂反应。
• Synthesis of Functionalized Oxazolones by a Sequence of Cu(II)- and Au(I)-Catalyzed Transformations
  作者：Florin M. Istrate、Andrea K. Buzas、Igor Dias Jurberg、Yann Odabachian、Fabien Gagosz

  DOI：10.1021/ol703077g

  日期：2008.3.1

  A study concerning a two-step sequence leading to the formation of diversely 1,5-disubstituted oxazolones is described. The mild conditions employed allow the efficient and rapid synthesis of a variety of such compounds via an initial Cu(II)-catalyzed coupling of a bromoalkyne with a secondary tert-butyloxycarbamate followed by a Au(I)-catalyzed cycloisomerization of the N-alkynyl tert-butyloxycarbamates thus obtained.