tert-butyl(diphenyl)(2-propynyloxy)silane | 110824-26-5

• 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(diphenyl)(2-propynyloxy)silane
• 英文别名: (t-butyldiphenyl)silyloxypropyne lithium
• CAS: 110824-26-5
• 化学式: C₁₉H₂₁LiOSi
• 分子量: 300.402
• InChiKey: SEOHZHKKOMBANE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.77
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 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：

  tert-butyl(diphenyl)(2-propynyloxy)silane 在 3 A molecular sieve 、 Celite 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 生成 8-[tert-butyl(diphenyl)silyl]oxy-5-oxooct-6-ynal
  参考文献：
  名称：

  通过乙烯基硅烷封端的阳离子环化反应合成（+）-二氢compactin和（+）-compactin

  摘要：

  描述了对八醇二醇1的两种对映选择性路线，其特征在于由乙烯基硅烷末端基团和苯二甲醇缩醛引发剂介导的阳离子多烯环化。还报道了进一步的转化，分别导致（+）-compactin和（+）-dihydrocompactin的形式和全部合成。

  DOI：

  10.1016/s0040-4039(00)92272-x

文献信息

• A stereoselective synthesis of medium-sized cyclic ethers by the intramolecular cyclization of linear hydroxyalkyl-propargylic alcohols assisted by Co2(CO)8
  作者：JoséM Palazón、Victor S Martín

  DOI：10.1016/0040-4039(95)00555-q

  日期：1995.5

  A highly efficient, mild and general cyclization reaction of hydroxy exo-(propargyl)Co2(CO)6 cations leading to medium-sized (6 to 9 membered) cyclic ethers is described. The reaction is highly stereoselective when defined stereocenters are encountered in the linear precursor, providing a way to obtain fused cyclic ethers in their enantiomeric forms.

  描述了羟基外-（炔丙基）Co 2（CO）6阳离子的高效，温和且通用的环化反应，导致中等大小（6至9元）的环状醚。当在线性前体中遇到确定的立体中心时，该反应是高度立体选择性的，从而提供了一种以对映体形式获得稠合环状醚的方法。
• Kondo, Kazuhiro; Kazuta, Kumiko; Saitoh, Atsushi, Heterocycles, 2003, vol. 59, # 1, p. 97 - 100
  作者：Kondo, Kazuhiro、Kazuta, Kumiko、Saitoh, Atsushi、Murakami, Yasuoki

  DOI：——

  日期：——
• Boron trifluoride–tetrahydrofuran complex: a superior trigger for the Yamaguchi–Hirao alkylation of lithio-acetylides by epoxides
  作者：Ann B Evans、David W Knight

  DOI：10.1016/s0040-4039(01)01414-9

  日期：2001.9

  Use of (BF3THF)-T-. complex in place of the usual (BF3OEt2)-O-. analogue in the Yamaguchi-Hirao alkylation of lithio- acetylides 2 by monosubstituted epoxides 3 gives consistently superior isolated yields (ca. 90%) of homopropargylic alcohols 1. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Practical alternatives for the synthesis of β-iodofurans by 5-endo-dig cyclisations of 3-alkyne-1,2-diols
  作者：Gamila M.M. El-Taeb、Ann B. Evans、Simon Jones、David W. Knight

  DOI：10.1016/s0040-4039(01)01112-1

  日期：2001.8

  Iodocyclisations of 3-alkyne-1,2-diols, obtained from acetylides and a-hydroxy-ketones or esters, give generally excellent yields of beta -iodofurans by 5-endo-dig cyclisation followed by dehydration. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Montmorillonite K-10 as a mild acid for the Nicholas reaction
  作者：Fernando R. Pinacho Crisóstomo、Romen Carrillo、Tomás Martín、Víctor S. Martín

  DOI：10.1016/j.tetlet.2005.02.118

  日期：2005.4

  The use of Montmorillonite K-10 as a convenient acid component in the Nicholas reaction is described. Its use permits functional selectivity, inter- and intramolecular reactions and convenience in the experimental conditions. A four-step one-pot [CO2(CO)(6)-acetylene complex formation, THP-removal, cyclization and complex cleavage] process permits the direct synthesis of 2-ethynyl-tetrahydrofuraii from 6-(tetrahydro-2H-pyran-2-yloxy)hex-1-yn-3-ol. (c) 2005 Elsevier Ltd. All rights reserved.