1-trimethylsilylsulfanyl-3-tert-butyl-6-(dimethylaminomethyl)benzene

• 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-trimethylsilylsulfanyl-3-tert-butyl-6-(dimethylaminomethyl)benzene
• 英文别名: 1-(4-tert-butyl-2-trimethylsilylsulfanylphenyl)-N,N-dimethylmethanamine
• 化学式: C₁₆H₂₉NSSi
• 分子量: 295.564
• InChiKey: OENJDOALGFFVHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.97
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 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：

  1-trimethylsilylsulfanyl-3-tert-butyl-6-(dimethylaminomethyl)benzene 、 aluminum (III) chloride 以 氘代苯 为溶剂， 反应 2.0h， 生成 [AlCl2{S(C6H3-2-CH2NMe2-5-tBu)}-κ2S,N]
  参考文献：
  名称：

  Aminoarenethiolate Aluminum Complexes: Synthesis, Characterization, and Use in l-Lactide Polymerization

  摘要：

  Reaction of AlMe3 with S(SiMe3)(C6H3-2-CH2NRR'-5-Bu-t) (RR' = C5H10 (1a), C4H8 (1b), Me-2 (1c)), at ambient temperature, affords the amino adducts [AlMe3{S(SiMe3)(C6H3-2-CH2NRR'-5-Bu-t)}-kappa N] (RR' = C5H10 (2a), C4H8 (2b), Me-2 (2c)), which undergo TMS elimination upon heating to give the monomeric aminoarenethiolate aluminum complexes [AlMe2{S(C6H3-2-CH2NRR'-5-Bu-t)-kappa S-2,N}] (RR' = C5H10 (3a), C4H8 (3b), Me-2 (3c)). Following the same procedure, treatment of AlCl2Me and AlCl3 with 1 yields analogous aminoarenethiolate aluminum complexes with different degrees of methylation, the chloro methyl and dichloro complexes [AlClMe{S(C6H3-2-CH2NRR'-5-Bu-t)-kappa S-2,N}] (RR' = C5H10 (4a), C4H8 (4b), Me-2 (4c)) and [AlCl2{S(C6H3-2-CH2NRR'-5-Bu-t)}-kappa S-2,N] (RR' = C5H10 (5a), C4H8 (5b) Me2 (5c)), respectively. These complexes have been characterized by multinuclear NMR spectroscopy and elemental analysis. Moreover, the molecular structures of 3a,b have been determined by X-ray diffraction methods. Aluminum complexes 3 have been investigated for the ring-opening polymerization (ROP) of L-lactide, achieving high conversions in relatively short periods of time. The PLAs obtained feature an aminoarenethiolate end functionality, as inferred from MALDI-TOF mass analysis.

  DOI：

  10.1021/om400111f
• 作为产物：
  描述：

  4-叔丁基苄溴 在 叔丁基锂 、 sulfur 作用下， 以 四氢呋喃 、 二氯甲烷 、 正戊烷 为溶剂， 反应 5.0h， 生成 1-trimethylsilylsulfanyl-3-tert-butyl-6-(dimethylaminomethyl)benzene
  参考文献：
  名称：

  氨基芳硫醇盐-铜（I）催化的芳基溴化物胺化。

  摘要：

  [反应，结构：见正文]已知氨基芳硫醇盐-铜（I）络合物是形成碳-碳键的有效催化剂。在这里，我们显示了这些硫醇盐-铜（I）配合物对碳-氮键形成反应也有效的第一个例子。苄胺和咪唑与溴苯的N-芳基化反应仅在2.5％（摩尔）的氨基芳硫醇盐-铜（I）络合物存在下，在无溶剂条件下或在无溶剂条件下均可实现。

  DOI：

  10.1021/ol052113z

文献信息

• Aminoarenethiolate−Copper(I)-Catalyzed Amination of Aryl Bromides
  作者：Thomas Jerphagnon、Gerard P. M. van Klink、Johannes G. de Vries、Gerard van Koten

  DOI：10.1021/ol052113z

  日期：2005.11.1

  [reaction, structure: see text] Aminoarenethiolate-copper(I) complexes are known to be efficient catalysts for carbon-carbon bond formation. Here, we show the first examples that these thiolate-copper(I) complexes are efficient for carbon-nitrogen bond formation reactions as well. N-Arylation of benzylamine and imidazole with bromobenzene was achieved either in NMP as solvent or under solvent-free

  [反应，结构：见正文]已知氨基芳硫醇盐-铜（I）络合物是形成碳-碳键的有效催化剂。在这里，我们显示了这些硫醇盐-铜（I）配合物对碳-氮键形成反应也有效的第一个例子。苄胺和咪唑与溴苯的N-芳基化反应仅在2.5％（摩尔）的氨基芳硫醇盐-铜（I）络合物存在下，在无溶剂条件下或在无溶剂条件下均可实现。
• Aminoarenethiolate Aluminum Complexes: Synthesis, Characterization, and Use in <scp>l</scp>-Lactide Polymerization
  作者：Lorena Postigo、Marı́a del Carmen Maestre、Marta E. G. Mosquera、Tomás Cuenca、Gerardo Jiménez

  DOI：10.1021/om400111f

  日期：2013.5.13

  Reaction of AlMe3 with S(SiMe3)(C6H3-2-CH2NRR'-5-Bu-t) (RR' = C5H10 (1a), C4H8 (1b), Me-2 (1c)), at ambient temperature, affords the amino adducts [AlMe3S(SiMe3)(C6H3-2-CH2NRR'-5-Bu-t)}-kappa N] (RR' = C5H10 (2a), C4H8 (2b), Me-2 (2c)), which undergo TMS elimination upon heating to give the monomeric aminoarenethiolate aluminum complexes [AlMe2S(C6H3-2-CH2NRR'-5-Bu-t)-kappa S-2,N}] (RR' = C5H10 (3a), C4H8 (3b), Me-2 (3c)). Following the same procedure, treatment of AlCl2Me and AlCl3 with 1 yields analogous aminoarenethiolate aluminum complexes with different degrees of methylation, the chloro methyl and dichloro complexes [AlClMeS(C6H3-2-CH2NRR'-5-Bu-t)-kappa S-2,N}] (RR' = C5H10 (4a), C4H8 (4b), Me-2 (4c)) and [AlCl2S(C6H3-2-CH2NRR'-5-Bu-t)}-kappa S-2,N] (RR' = C5H10 (5a), C4H8 (5b) Me2 (5c)), respectively. These complexes have been characterized by multinuclear NMR spectroscopy and elemental analysis. Moreover, the molecular structures of 3a,b have been determined by X-ray diffraction methods. Aluminum complexes 3 have been investigated for the ring-opening polymerization (ROP) of L-lactide, achieving high conversions in relatively short periods of time. The PLAs obtained feature an aminoarenethiolate end functionality, as inferred from MALDI-TOF mass analysis.