4-methyl-N,N-bis(3-(naphthalen-1-yl)prop-2-yn-1-yl)benzenesulfonamide

• 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: 4-methyl-N,N-bis(3-(naphthalen-1-yl)prop-2-yn-1-yl)benzenesulfonamide
• 英文别名: N,N-bis[3-(naphthalen-1-yl)prop-2-yl]tosylamine；4-methyl-N,N-bis(3-naphthalen-1-ylprop-2-ynyl)benzenesulfonamide
• 化学式: C₃₃H₂₅NO₂S
• 分子量: 499.633
• InChiKey: UEZPRRCCFQWSTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  37
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-methyl-N,N-bis(3-(naphthalen-1-yl)prop-2-yn-1-yl)benzenesulfonamide 在 Iron(III) nitrate nonahydrate 、 硝酸 作用下， 以 乙腈 为溶剂， 以23%的产率得到naphthalen-1-yl(4-(naphthalen-1-yl)-5,5-dinitro-1-tosyl-1,2,5,6-tetrahydropyridin-3-yl)methanone
  参考文献：
  名称：

  Synthesis of cyclic gem-dinitro compounds via radical nitration of 1,6-diynes with Fe(NO₃)₃·9H₂O

  摘要：

  通过使用Fe(NO3)3·9H2O作为硝化剂，通过对1,6-二炔基化合物进行硝化反应，获得了环状双硝基化合物。

  DOI：

  10.1039/c9ob00431a

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。
• Thermal and Au(I)-Catalyzed Intramolecular [4+2] Cycloaddition of Aryl-Substituted 1,6-Diynes for the Synthesis of Biaryl Compounds
  作者：Takanori Shibata、Ryo Fujiwara、Daisuke Takano

  DOI：10.1055/s-2005-871959

  日期：——

  1,6-Diynes, possessing aryl groups on their termini, undergo an intramolecular [4+2] cycloaddition via strained cyclic allene intermediates to give various biaryl compounds. Under thermal conditions, isomerization of the intermediates occurs, while, in the presence of a cationic gold catalyst, skeletal rearrangement is a major pathway.

  1,6-二炔在其末端具有芳基，通过紧张的环状丙二烯中间体进行分子内[4+2]环加成，得到各种联芳基化合物。在热条件下，中间体发生异构化，而在阳离子金催化剂的存在下，骨架重排是主要途径。
• 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.
• Synthesis of cyclic <i>gem</i>-dinitro compounds <i>via</i> radical nitration of 1,6-diynes with Fe(NO₃)₃·9H₂O
  作者：Xiaofei Yi、Kai Chen、Wei Chen、Wanzhi Chen、Miaochang Liu、Huayue Wu

  DOI：10.1039/c9ob00431a

  日期：——

  Cyclic gem-dinitro compounds were obtained via nitration of 1,6-diynes using Fe(NO₃)₃·9H₂O as the nitrating agent.

  通过使用Fe(NO3)3·9H2O作为硝化剂，通过对1,6-二炔基化合物进行硝化反应，获得了环状双硝基化合物。