4,4-bis(ethoxycarbonyl)-1-(2-methylphenyl)octa-1,6-diyne | 722496-81-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: 4,4-bis(ethoxycarbonyl)-1-(2-methylphenyl)octa-1,6-diyne
• 英文别名: Diethyl 2-but-2-ynyl-2-[3-(2-methylphenyl)prop-2-ynyl]propanedioate
• CAS: 722496-81-3
• 化学式: C₂₁H₂₄O₄
• 分子量: 340.419
• InChiKey: NGQTZMLELFOAAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,4-二甲氧基-2-丁炔 、 4,4-bis(ethoxycarbonyl)-1-(2-methylphenyl)octa-1,6-diyne 在 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 EtDUPHOS 作用下， 以 xylene 为溶剂， 生成 (-)-2,3-dihydro-2,2-bis(ethoxycarbonyl)-5,6-bis(methoxymethyl)-4-methyl-7-(2-methylphenyl)-1H-indene 、 (+)-2,3-dihydro-2,2-bis(ethoxycarbonyl)-5,6-bis(methoxymethyl)-4-methyl-7-(2-methylphenyl)-1H-indene
  参考文献：
  名称：

  Iridium Complex-Catalyzed Highly Enantio- and Diastereoselective [2+2+2] Cycloaddition for the Synthesis of Axially Chiral Teraryl Compounds

  摘要：

  An asymmetric [2+2+2] cycloaddition of an alpha,omega-diyne, possessing ortho-substituted aryl groups on its terminus, and a monoalkyne with oxygen functionalities gave various axially chiral teraryl compounds. The coupling proceeded with extremely high enantio- (>99.5% ee) and diastereoselectivities (dl/meso = >95/5) when catalyzed by an iridium-chiral phosphine complex. As the products were readily transformed into diol compounds by deprotection without racemization, the present procedure provides access to a new chiral pool of diol compounds with C2 symmetry.

  DOI：

  10.1021/ja048131d
• 作为产物：
  描述：

  diethyl 2-(but-2-yn-1-yl)malonate 、 1-(3-bromoprop-1-yn-1-yl)-2-methylbenzene 在 sodium hydride 作用下， 生成 4,4-bis(ethoxycarbonyl)-1-(2-methylphenyl)octa-1,6-diyne
  参考文献：
  名称：

  Iridium Complex-Catalyzed Highly Enantio- and Diastereoselective [2+2+2] Cycloaddition for the Synthesis of Axially Chiral Teraryl Compounds

  摘要：

  An asymmetric [2+2+2] cycloaddition of an alpha,omega-diyne, possessing ortho-substituted aryl groups on its terminus, and a monoalkyne with oxygen functionalities gave various axially chiral teraryl compounds. The coupling proceeded with extremely high enantio- (>99.5% ee) and diastereoselectivities (dl/meso = >95/5) when catalyzed by an iridium-chiral phosphine complex. As the products were readily transformed into diol compounds by deprotection without racemization, the present procedure provides access to a new chiral pool of diol compounds with C2 symmetry.

  DOI：

  10.1021/ja048131d