1,2-dimesitylethane | 4674-23-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 1,2-dimesitylethane
• 英文别名: 1,2-Bis(2,4,6-trimethylphenyl)ethan；1,2-bis(2,4,6-trimethylphenyl)ethane；2,2',4,4',6,6'-hexamethyldibenzyl；1,2-Dimesityl-ethan；1,2-Di(2,4,6-trimethylphenyl)ethane；1,3,5-trimethyl-2-[2-(2,4,6-trimethylphenyl)ethyl]benzene
• CAS: 4674-23-1
• 化学式: C₂₀H₂₆
• 分子量: 266.426
• InChiKey: TUIQGWQRVMJCAK-UHFFFAOYSA-N

物化性质

• 熔点：
  117-117.5 °C
• 沸点：
  130-190 °C(Press: 3.5 Torr)
• 密度：
  0.949±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,2-dimesitylethane 在 sodium sulfide 、 氢溴酸 、 溴棕三甲铵 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 正庚烷 、 水 、 苯 为溶剂， 反应 72.53h， 生成 anti-4,6,8,12,14,16-hexamethyl-1-methylthio[2.2]metacyclophane
  参考文献：
  名称：

  Synthesis, Reactions, and Structural and NMR Features of [2.2]Metacyclophane Monoenes and Their Tricarbonylchromium and Cyclopentadienyliron(+) Complexes

  摘要：

  8,16-Dimethyl-, 5,8,13,16-tetramethyl, and 4,6,8,12,14,16-hexamethyl[2,2]metacyclophanene have been synthesized from the corresponding methyl-substituted 3-thia[3.2]metacyclophane precursors via a Wittig rearrangement-Hofmann elimination procedure. Simple addition of bromine or similar electrophiles to the bridge double bond of the cyclophane monoenes did not occur; rather, the methyl-substituted dihydropyrenes were formed. However, mono- and bis-tricarbonylchromium and monocyclopentadienyliron complexes were obtained using ligand-exchange reactions. Addition of bromine to the cyclophane bridge double bond of the iron complex did occur, but unusually slowly. Surprisingly, debromination rather than dehydrobromination occurred when the dibromo addition product was treated with a variety of bases. Photoisomerization of the monoenes and nucleophilic substitution of the metal complexes was also investigated. The geometries of the monoenes and their complexes were compared to the cyclophanes and the cyclophanedienes and to the monothia- and dithiacyclophanes, by comparison of X-ray and calculated structural data and NMR spectroscopic data. Introduction of double bonds into the cyclophane bridges causes the cyclophane step to be less steep but increases distortion of the internal atoms out of the plane of the benzene rings. Making the bridges nonidentical also causes a sideways twist of the step.

  DOI：

  10.1021/jo990721k
• 作为产物：
  描述：

  2,4,6-三甲基苯甲醛 在 盐酸 、 乙醚 、 镍 、 甲基环己烷 作用下， 100.0~150.0 ℃ 、13.73 MPa 条件下， 生成 1,2-dimesitylethane
  参考文献：
  名称：

  HIGHLY HINDERED STILBENES

  摘要：

  DOI：

  10.1021/jo01189a011

文献信息

• Facile reductive coupling of benzylic halides with ferrous oxalate dihydrate
  作者：Jitender M. Khurana、Sushma Chauhan、Golak C. Maikap

  DOI：10.1039/b211792d

  日期：2003.5.15

  Facile reductive coupling of benzylic halides is reported with ferrous oxalate dihydrate in DMF or HMPA under nitrogen atmosphere at 155–160 °C. The coupling is proposed to proceed by two successive oxidative additions of benzylic halides to ferrous oxalate to give an intermediate organoiron complex which undergoes concerted dimerization to give the corresponding reductively coupled dimers in high yields.

  报道称，在氮气气氛下，使用二水合草酸亚铁在DMF或HMPA中，于155-160°C的温度下，可以轻松实现苄基卤化物的还原耦合反应。该耦合反应被认为是通过苄基卤化物对草酸亚铁的两次连续氧化加成，生成一种中间体有机铁配合物，该配合物随后经历协同二聚反应，以高产率得到相应的还原耦合二聚体。
• Orthoamide, LIX. Formyl-aalen [Tris(diformylamino)methan] – ein neues Formylierungsmittel für aktivierte Aromaten/Orthoamides, LIX. Formyl-aalen [Tris(diformylamino)methane] – a New Formylating Reagent for Activated Aromatic Compounds
  作者：Willi Kantlehner、Erwin Haug、Oliver Scherr、Georg Ziegler

  DOI：10.1515/znb-2002-1116

  日期：2002.11.1

  In the presence of strong Lewis acids such as aluminum chloride or boron trichloride, formyl-aalen [tris(diformylamino)methane] (3) acts as a formylating reagent for aromatic alkane compounds and aromatic ethers. The orthoamide 3 delivers three formyl groups for the formylation process. Thus toluene, cumene, tert-butylbenzene, hexylbenzene, ο-xylene, ρ-cymene, biphenyl, anisole, diphenylether and 1

  在强路易斯酸（如氯化铝或三氯化硼）存在下，甲酰丙二烯 [三（二甲酰氨基）甲烷] (3) 作为芳烃化合物和芳醚的甲酰化试剂。orthoamide 3 为甲酰化过程提供三个甲酰基。因此，甲苯、枯烯、叔丁基苯、己基苯、邻二甲苯、对异丙基苯、联苯、苯甲醚、二苯醚和 1,3-二甲氧基苯可以在 1,2-二氯乙烷中甲酰化。在这些反应中，3 和氯化铝的使用摩尔比应为 1:6 至 1:9。
• Abnormal reduction of N-nitroso-bis-(2,4,6-trimethylbenzyl)amine with lithium aluminium hydride
  作者：Robert W. Gleason、Jules F. Paulin

  DOI：10.1039/c39730000098

  日期：——

  Reduction of the title compound with lithium aluminium hydride proceeds with evolution of nitrogen and the formation of 1,2-bis-(2,4,6-trimethylphenyl)ethane in 78% yield.

  用氢化铝锂还原标题化合物随着氮的释放和1，2-双-（2,4,6-三甲基苯基）乙烷的形成而进行，产率为78％。
• Photochemistry of .alpha.-(o-tolyl)acetone and some derivatives: triplet .alpha.-cleavage and singlet .delta.-hydrogen abstraction
  作者：Taehee Noh、Xue Gong Lei、Nicholas J. Turro

  DOI：10.1021/ja00061a008

  日期：1993.4

  this reaction reveals that the photolysis of solutions of TA does produce an indanol, albeit as a minor product. Similarly, photolysis of benzene solutions of o-tolylmethyl benzyl ketone (TBK) and o-tolylmethyl cyclohexyl ketone (TCK) results in the formation of indanols as minor products (ca. 5-10%). However, the photolysis of mesitylmethyl benzyl ketone (MBK) yields an indanol in significant yield

  据报道，α-(0-toly1) 丙酮 (TA) 在 2-丙醇中的光解不会产生预期从所得 1,5-双自由基的氢提取和环化中得到的茚满醇产物。对该反应的重新研究表明，TA 溶液的光解确实产生了茚满醇，尽管只是次要产物。类似地，邻甲苯基甲基苄基酮 (TBK) 和邻甲苯基甲基环己基酮 (TCK) 的苯溶液的光解导致形成茚满醇作为次要产物（约 5-10%）。然而，甲基苯甲基酮 (MBK) 的光解以显着的产率（约 40%）产生茚满醇。在所有情况下，由α-裂解产生的苄基自由基的自由基重组预期的二苯乙烷（DPE）作为主要产物产生。为了确定α-（0-甲苯基）丙酮光解形成茚满醇的合成限制，研究了这些光解的机理。用四甲基-1,2-二氧杂环丁烷在 70 OC 热解产生的三线态丙酮敏化、异戊二烯对酮消失的猝灭以及茚满醇形成的异戊二烯猝灭和荧光表明，α-裂解主要发生在三线态并且 b-氢提取完全发生在单线态。发现乙腈中二苄基酮
• (Tetramethylcyclobutadiene)cobalt complexes 7. Mono- and dinuclear arene complexes containing the [(C4Me4)Co]+ fragment
  作者：D. A. Loginov、A. A. Pronin、L. S. Shul’pina、E. V. Mutseneck、Z. A. Starikova、P. V. Petrovskii、A. R. Kudinov

  DOI：10.1007/s11172-008-0084-x

  日期：2008.3

  The mononuclear arene complexes [Cb*Co(arene)]+ (3a–g; Cb* = C4Me4; arene is biphenyl (a), diphenylmethane (b), 1,2-diphenylethane (c), diphenyl ether (d), p-terphenyl (e), 1,2-dimesitylethane (f), or 1,3-dimesitylpropane (g)) were synthesized by the reactions of arenes either with the benzene complex [Cb*Co(C6H6)]+ (1) under visible light irradiation or with the acetonitrile derivative [Cb*Co(MeCN)3]+

  单核芳烃配合物 [Cb*Co(芳烃)]+ (3a–g; Cb* = C4Me4; 芳烃是联苯 (a), 二苯甲烷 (b), 1,2-二苯乙烷 (c), 二苯醚 (d),对三联苯 (e)、1,2-二甲基丙烷 (f) 或 1,3-二甲基丙烷 (g)) 是通过芳烃与苯络合物 [Cb*Co(C6H6)]+ (1) 的反应合成的在可见光照射下或与乙腈衍生物 [Cb*Co(MeCN)3]+ (2) 在回流的 THF 中反应。2 与 1,2-二苯乙烷、1,3-二甲苯基丙烷和对三联苯以 2:1 的比例反应得到双核配合物 [Cb*Co(μ-η:η-芳烃)CoCb*] 2+ (4c,e,g)。双核芳烃配合物的稳定性通过 DFT 计算进行估计。复合物 [3a]PF6 和 [3e]PF6 的结构通过 X 射线衍射确定。