1,3-dihydro-4,7-di(naphthalen-1-yl)-5,6-bis(hydroxymethyl)-2-tosylindoline

• 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: 1,3-dihydro-4,7-di(naphthalen-1-yl)-5,6-bis(hydroxymethyl)-2-tosylindoline
• 英文别名: [6-(Hydroxymethyl)-2-(4-methylphenyl)sulfonyl-4,7-dinaphthalen-1-yl-1,3-dihydroisoindol-5-yl]methanol
• 化学式: C₃₇H₃₁NO₄S
• 分子量: 585.723
• InChiKey: APMVXJMMJMCKLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  43
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  86.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4,7-Di-naphthalen-1-yl-5,6-bis-(tetrahydro-pyran-2-yloxymethyl)-2-(toluene-4-sulfonyl)-2,3-dihydro-1H-isoindole 在 4-甲基苯磺酸吡啶 作用下， 以 乙醇 为溶剂， 生成 1,3-dihydro-4,7-di(naphthalen-1-yl)-5,6-bis(hydroxymethyl)-2-tosylindoline
  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

文献信息

• Iridium-Catalyzed Enantioselective [2+2+2] Cycloaddition of Diynes and Monoalkynes for the Generation of Axial Chiralities
  作者：Takanori Shibata、Yoshikazu Arai、Kyoko Takami、Kyoji Tsuchikama、Takayoshi Fujimoto、Satoshi Takebayashi、Kentaro Takagi

  DOI：10.1002/adsc.200600317

  日期：2006.11

  A highly enantioselective intermolecular [2+2+2] cycloaddition of alkynes was catalyzed by a chiral iridium complex. Symmetrical and unsymmetrical diynes, and monoalkynes possessing functional group(s) were subjected to the reaction and various types of axially chiral compounds possessing biaryl skeletons were obtained in good to excellent enantiomeric excesses.

  炔烃的高度对映选择性分子间[2 + 2 + 2]环加成反应被手性铱配合物催化。使对称和不对称的二炔和具有一个或多个官能团的单炔进行反应，并以良好至优异的对映体过量获得了各种类型的具有联芳基骨架的轴向手性化合物。
• Iridium Complex-Catalyzed Highly Enantio- and Diastereoselective [2+2+2] Cycloaddition for the Synthesis of Axially Chiral Teraryl Compounds
  作者：Takanori Shibata、Takayoshi Fujimoto、Kazuhisa Yokota、Kentaro Takagi

  DOI：10.1021/ja048131d

  日期：2004.7.14

  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.