3-(tert-butyldimethylsiloxy)propynyldiethylalane | 89731-32-8

• 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: 3-(tert-butyldimethylsiloxy)propynyldiethylalane
• CAS: 89731-32-8
• 化学式: C₁₃H₂₇AlOSi
• 分子量: 254.424
• InChiKey: PBHDPNOZBMLBBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.09
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 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：

  3-(tert-butyldimethylsiloxy)propynyldiethylalane 在 喹啉 、 Lindlar's catalyst 氢气 作用下， 以 甲苯 、 苯 为溶剂， -78.0~5.0 ℃ 、101.33 kPa 条件下， 反应 3.0h， 生成 methyl (2S)-2-((E)-3-((tert-butyldimethylsilyl)oxy)prop-1-en-1-yl)-5-oxocyclopentane-1-carboxylate
  参考文献：
  名称：

  一种新型的碘化锂促进的乙烯基环丙烷-环戊烯重排：高效合成双环[3.3.0] oct-6-en-2-one通用构建基多环戊烷天然产物

  摘要：

  双环[3.3.0] oct-6-en-2-one，一种多环戊烷天然产物的通用结构单元，已通过钯催化的环丙烷化和碘化锂促进的乙烯基环丙烷重排反应，由2-甲氧基羰基-2-环戊烯酮有效地合成。

  DOI：

  10.1016/s0040-4039(00)84670-5
• 作为产物：
  描述：

  3-(t-butyldimethylsilyloxy)prop-1-ynyllithium 生成 3-(tert-butyldimethylsiloxy)propynyldiethylalane
  参考文献：
  名称：

  MAGDZINSKI, LEON;FRASER-REID, BERT, CAN. J. CHEM., 66,(1988) N1, C. 2819-2825

  摘要：

  DOI：

文献信息

• Vicinal alkynylation-alkylation via a tandem michael addition - transition metal catalyzed alkylation reaction
  作者：Barry M. Trost、Chao-Jun Li

  DOI：10.1016/s0040-4039(00)77591-5

  日期：1993.4

  A protocol whereby addition of alkynylalanes to alkylidenemalonates is followed by palladium catalyzed allylation permits vicinal β-alkynylation α-allylation in a single operation

  一种方案，其中在炔属丙二酸烷基酯中添加炔基丙氨酸，然后进行钯催化的烯丙基化，可在一次操作中实现邻位β-炔基α-烯丙基化
• Magdzinski, Leon; Fraser-Reid, Bert, Canadian Journal of Chemistry, 1988, vol. 66, p. 2819 - 2825
  作者：Magdzinski, Leon、Fraser-Reid, Bert

  DOI：——

  日期：——
• Regiocontrolled Ring Opening of Monoprotected 2,3-Epoxy-1,4-diols by Using Alkynyl Aluminum Reagents: Synthesis of Differentially Monoprotected Alkynyl Triol Derivatives
  作者：José Prieto、Jaileen Torres、Raul Rodríguez-Berrios

  DOI：10.1055/s-0033-1340332

  日期：——

  The regioselectivity of the epoxide ring-opening reaction of cis and trans TIPS-monoprotected 2,3-epoxy-1,4-diols with diethylalkynyl aluminum reagents was studied. Alane and alanate conditions in toluene or dichloromethane were explored. Alkynyl attack at the C2 epoxide carbon was favored under both the alane and alanate conditions in toluene, whereas C3 attack was preferred in dichloromethane. The best regioselectivities were obtained by using the alanate conditions in toluene. This methodology provides access to differentially monoprotected alkynyl triols with high diastereoselectivity. These compounds are useful building blocks for polypropionate synthesis and are precursors for the introduction of the hydroxymethyl moiety found in some polyketide systems.
• Highly efficient synthesis of 13-dehydroprostaglandins by 1,4-addition reaction of alkynyl .omega. side-chain unit onto a cyclopentenone framework
  作者：Toshiharu Yoshino、Sentaro Okamoto、Fumie Sato

  DOI：10.1021/jo00010a004

  日期：1991.5

  Optically active 2-((diethylamino)methyl)-4-siloxy-2-cyclopentenone (2) reacts with a diethyl(3-(tert-butyldimethylsiloxy)-1-alkynyl) aluminum compound via 1,4-addition pathway to afford the enone 5, useful intermediate for synthesis of PGs via two-component coupling process, in excellent yield, thus making it easy to synthesize 13-dehydro-PGs.
• YOSHINO, TOSHIHARU;OKAMOTO, SENTARO;SATO, FUMIE, J. ORG. CHEM., 56,(1991) N0, C. 3205-3207
  作者：YOSHINO, TOSHIHARU、OKAMOTO, SENTARO、SATO, FUMIE

  DOI：——

  日期：——