5,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-nona-2,7-diyne

• 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: 5,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-nona-2,7-diyne
• 英文别名: Tert-butyl-[2-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-but-2-ynylhex-4-ynoxy]-dimethylsilane；tert-butyl-[2-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-but-2-ynylhex-4-ynoxy]-dimethylsilane
• 化学式: C₂₃H₄₄O₂Si₂
• 分子量: 408.772
• InChiKey: XVLKURGXLTYPFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.84
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-nona-2,7-diyne 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以171 mg的产率得到2,2-di(2-butyn-1-yl)-1,3-propanediol
  参考文献：
  名称：

  Synthesis of spiro bis(1,2,3-triazolium) salts as chiral ionic liquids

  摘要：

  Unique chiral spiro ionic liquids based on 1,2,3-triazolium salts were synthesized via an intramolecular double Huisgen reaction. The optical resolution of the liquid precursors and subsequent dialkylations leads to chiral spiro triazolium salts on a gram scale. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.09.152
• 作为产物：
  描述：

  4,4-bis(t-butyldimethylsilyloxymethyl)-1,6-heptadiyne 、 碘甲烷 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 2.0h， 以100%的产率得到5,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-nona-2,7-diyne
  参考文献：
  名称：

  Synthesis of spiro bis(1,2,3-triazolium) salts as chiral ionic liquids

  摘要：

  Unique chiral spiro ionic liquids based on 1,2,3-triazolium salts were synthesized via an intramolecular double Huisgen reaction. The optical resolution of the liquid precursors and subsequent dialkylations leads to chiral spiro triazolium salts on a gram scale. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.09.152

文献信息

• Highly Stereo- and Regioselective Hydrocarboxylation of Diynes with Carbon Dioxide
  作者：Tao Cao、Shengming Ma

  DOI：10.1021/acs.orglett.6b00028

  日期：2016.4.1

  A nickel-catalyzed three-component hydrocarboxylation of diynes with ZnEt2 and CO2 (1 atm) is disclosed. With this method, symmetric/nonsymmetric diynes could be reacted smoothly with very high stereo- and regioselectivity, affording conjugated 2,4-alkadienoic acids incorporated with five- or six-membered rings efficiently. A stepwise non-oxidative cyclometalation mechanism was proposed based on careful

  公开了用ZnEt 2和CO 2（1atm）的二炔的镍催化的三组分加氢羧化。用这种方法，对称/不对称二炔可以以非常高的立体选择性和区域选择性平滑反应，从而有效地提供了结合有五元或六元环的共轭2,4-链二烯酸。在仔细的机理研究的基础上，提出了一种逐步的非氧化性环金属化机理。
• Atroposelective Construction of Carbon–Boron Axial Chirality through Rh-Catalyzed [2 + 2 + 2] Cycloaddition
  作者：Yifan Ping、Xiaofan Shi、Ming Lei、Jianbo Wang

  DOI：10.1021/acscatal.4c00428

  日期：2024.4.5

  Axially chiral compounds have widespread applications in many fields. While significant progress has been made for the asymmetric synthesis of atropisomers consisting of C–C bonds, an efficient approach for the construction of C–B atropisomers is still lacking. Herein, we report a practical method for atroposelective synthesis of axially chiral arylboron compounds through Rh-catalyzed [2 + 2 + 2] cycloaddition

  轴向手性化合物在许多领域具有广泛的应用。虽然由C-C键组成的阻转异构体的不对称合成已经取得了重大进展，但仍然缺乏构建C-B阻转异构体的有效方法。在此，我们报道了一种通过 Rh 催化的 [2 + 2 + 2] 环加成反应选择性合成轴向手性芳基硼化合物的实用方法。该反应表现出广泛的底物范围和良好的官能团耐受性，从而提供了一种有效的方案，以高产率和良好的对映体控制获得各种 C-B 阻转异构体。这些 C-B 阻转异构体的实用性已通过多种转化为高价值化合物（如手性膦配体和荧光分子）得到充分证明。机理实验和 DFT 计算提供了对反应机理以及对映体控制起源的见解。
• Efficient Nickel-Catalyzed [2 + 2 + 2] Cycloaddition of CO₂ and Diynes
  作者：Janis Louie、John E. Gibby、Marc V. Farnworth、Thomas N. Tekavec

  DOI：10.1021/ja027438e

  日期：2002.12.1

  A mild and general route for preparing 2-pyrones from CO2 and diynes is described. Under only 1 atm of CO2, excellent yields of pyrone are obtained using catalytic amounts of Ni(COD)2 and imidazolylidene ligand, IPr. In addition, stoichiometric reactions between the isolated complex Ni(IPr)2, diynes, and CO2 suggest that the pathway involves initial reaction with CO2 as the key step.
• Synthesis of spiro bis(1,2,3-triazolium) salts as chiral ionic liquids
  作者：Yasushi Yoshida、Shinobu Takizawa、Hiroaki Sasai

  DOI：10.1016/j.tetlet.2011.09.152

  日期：2011.12

  Unique chiral spiro ionic liquids based on 1,2,3-triazolium salts were synthesized via an intramolecular double Huisgen reaction. The optical resolution of the liquid precursors and subsequent dialkylations leads to chiral spiro triazolium salts on a gram scale. (C) 2011 Elsevier Ltd. All rights reserved.