1-(tert-butyldimethylsiloxy)-4-methyl-6-phenyl-2-hexyn-3-yl methyl carbonate | 1082069-16-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(tert-butyldimethylsiloxy)-4-methyl-6-phenyl-2-hexyn-3-yl methyl carbonate
• 英文别名: 1-(tert-butyldimethylsiloxy)-4-methyl-6-phenyl-2-hexyn-4-yl methyl carbonate；PhCH2CH2CMe(OCO2Me)CCCH2OTBS
• CAS: 1082069-16-6
• 化学式: C₂₁H₃₂O₄Si
• 分子量: 376.568
• InChiKey: FKEDCPWXPGWISC-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.19
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-(tert-butyldimethylsiloxy)-4-methyl-6-phenyl-2-hexyn-3-yl methyl carbonate 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成
  参考文献：
  名称：

  α-Fluoroallenoate Synthesis via N-Heterocyclic Carbene-Catalyzed Fluorination Reaction of Alkynals

  摘要：

  The first catalytic alpha-fluoroallenoate synthesis is described. With a suitable combination of N-heterocyclic carbene precatalyst, base, and fluorine reagent, the reaction proceeded smoothly to yield a wide range of alpha-fluoroallenoates with excellent chemoselectivity. These substituted alpha-fluorinated allenoates have been synthesized for the first time, and they are versatile synthetic intermediates toward other useful fluorine-containing building blocks.

  DOI：

  10.1021/acs.orglett.5b03615
• 作为产物：
  描述：

  6-((tert-butyldimethylsilyl)oxy)-3-methyl-1-phenylhex-4-yn-3-ol 、 氯甲酸甲酯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 生成 1-(tert-butyldimethylsiloxy)-4-methyl-6-phenyl-2-hexyn-3-yl methyl carbonate
  参考文献：
  名称：

  α-Fluoroallenoate Synthesis via N-Heterocyclic Carbene-Catalyzed Fluorination Reaction of Alkynals

  摘要：

  The first catalytic alpha-fluoroallenoate synthesis is described. With a suitable combination of N-heterocyclic carbene precatalyst, base, and fluorine reagent, the reaction proceeded smoothly to yield a wide range of alpha-fluoroallenoates with excellent chemoselectivity. These substituted alpha-fluorinated allenoates have been synthesized for the first time, and they are versatile synthetic intermediates toward other useful fluorine-containing building blocks.

  DOI：

  10.1021/acs.orglett.5b03615

文献信息

• Copper(I)-Catalyzed Substitution of Propargylic Carbonates with Diboron: Selective Synthesis of Multisubstituted Allenylboronates
  作者：Hajime Ito、Yusuke Sasaki、Masaya Sawamura

  DOI：10.1021/ja806602h

  日期：2008.11.26

  A versatile synthetic method for the preparation of the allenylboronates, Cu(I)-catalyzed reaction of propargylic carbonates with a diboron, is described. A Cu(O-t-Bu)-Xantphos catalyst system was effective for the preparation of various allenylboron compounds, allenylboronates with different substitution patterns, those with functional groups, and an axially chiral one. The Lewis acid promoted stereoselective addition to aldehydes leading to homopropargylic alcohols showed the usefulness of the new allenylboronates.