1-[2-(methylthio)-phenyl]-3-(dimethytlamino)-1-propyne | 448948-97-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-[2-(methylthio)-phenyl]-3-(dimethytlamino)-1-propyne
• 英文别名: 1-(2-methylthiophenyl)-3-(dimethylamino)-1-propyne；N,N-dimethyl-3-(2-methylsulfanylphenyl)prop-2-yn-1-amine
• CAS: 448948-97-8
• 化学式: C₁₂H₁₅NS
• 分子量: 205.324
• InChiKey: LSZOQSDDYNURBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  28.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  palladium dichloride 、 lithium chloride 、 1-[2-(methylthio)-phenyl]-3-(dimethytlamino)-1-propyne 以 甲醇 为溶剂， 以67%的产率得到Pd[κ1-C,κ1-Nκ1-SMe-C=(MeS-2-C6H4)C(Cl)CH2NMe2]Cl
  参考文献：
  名称：

  异取代炔烃的反式氯金属化：不对称钯YCY'（Y，Y'= NR 2，PPh 2，OPPh 2和SR）“ Pincer”配合物的便捷进入

  摘要：

  由杂取代炔烃的氯钯钯化已经公开了一种简单有效的制备不对称钯YCY'PdCl（Y，Y'= NR 2，Py，PPh 2，OPPh 2和SR）“钳”配合物的方法。该方法可耐受多种炔基官能团（胺，吡啶，硫醚，膦和次膦酸酯），并允许制备包含不同金属化环尺寸的palladacycles。因此，Li 2 PdCl 4与杂取代炔烃Me 2 NCH 2 C⋮CCH 2 CH 2 Y（Y = S- t- Bu，NMe 2，PPh 2和OPPh 2）1 - 4，得到“夹钳”钯化合物（ME 2 NCH 2（CL）C CCH 2 CH 2 Y型κ Ñ，κ Ç，κ ÿ）的PdCl 7 - 10，以高收率。在相同的反应条件下的chloropalladation ø -MeSC 6 ħ 4 Ç⋮CCH 2 NME 2，5，并ö -NC 5 H ^ 4 Ç⋮CCH 2 CH 2 S-吨-Bu，6，产率（C 6 H ^ 4（ø

  DOI：

  10.1021/om011002a

文献信息

• Atropisomerism in palladacycles derived from the chloropalladation of heterosubstituted alkynes
  作者：Mara L. Zanini、Mario R. Meneghetti、Günter Ebeling、Paolo R. Livotto、Frank Rominger、Jairton Dupont

  DOI：10.1016/s0020-1693(03)00011-2

  日期：2003.7

  The chloropalladation of 2-substituted phenyl N,N-propargylamines, Y-2-C6H4C=CCH2NMe2 (1a, Y = H; 2a, Y = CF3; 3a, Y = OMe: 4a. Y = SMe and 5a, Y = NH2) affords palladacycles in different ratios of isomers (geometric and atropisomers). In solution, the parent alkyne (Y = H) and the CF3 substituted derivative generate a mixture of cisoid and transoid chloro-bridged dimer palladacycles of the type Pd[kappa(1)-C, kappa(1)-N-C=(Y-2-C6H4)C(cl)CH2NMe2](mu-Cl)}(2). Moreover, in the case in the case of Y = CF3 palladacyclic derivative each of the geometric isomers comprises a mixture of two diastereoisomers due to the restricted rotation of the C(vinyl)-C(aryl) sigma bond (atropisomers). Palladacycles 1a (Y = H) and 2a (Y = CF3) crystallize as the single transoid and cisoid-anti isomer. respectively. The OMe substituted alkyne yields a similar dimeric compound that crystallizes as a single cisoid-anti isomer. In solution this dimeric compound is in fast equilibrium with a monomeric pincer compound of the type Pd[kappa(1)-C, kappa(1)-N, kappa(1)-O-C=(MeO-2-C6H4)C(Cl)CH2NMe2](Cl) assisted through the weak coordination of the OMe group. Pincer palladacycles Pd[kappa(1)-C, kappa(1)-N, kappa(1)-Y-C=(Y-2-C6H4)C(Cl)CH2NMe2](Cl) (Y = SMe and NH2) were the sole products obtained in the chloropalladation of alkynes 4a and 5a. The bridge splitting reaction of the dimeric palladacycles 1b-3b with pyridine is highly selective, affording exclusively the corresponding monomeric compounds 1c-3c. The monomeric palladacycle 2d, which comprises a mixture of two atropisomers (2:1 ratio of antilsyn) was obtained from the reaction of 2b with 2-methylpyridine. Theoretical calculations indicated that the anti isomer of 2d is 5.42 kJ mol(-1) more stable than its syn isomer. (C) 2003 Elsevier Science B.V. All rights reserved.