1,4-bis(hexyloxy)-2,3-dimethylbenzene | 139200-76-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,4-bis(hexyloxy)-2,3-dimethylbenzene
• 英文别名: 1,4-Dihexoxy-2,3-dimethylbenzene
• CAS: 139200-76-3
• 化学式: C₂₀H₃₄O₂
• 分子量: 306.489
• InChiKey: VTLWAWYVAHLKIE-UHFFFAOYSA-N

物化性质

• 沸点：
  406.9±40.0 °C(Predicted)
• 密度：
  0.914±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  22
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,4-bis(hexyloxy)-2,3-dimethylbenzene 在 溴 作用下， 以 氯仿 为溶剂， 反应 1.25h， 以90%的产率得到1-bromo-2,5-bis-hexyloxy-3,4-dimethylbenzene
  参考文献：
  名称：

  Organic Crystal Engineering with 1,4-Piperazine-2,5-diones. 8. Synthesis, Crystal Packing, and Thermochemistry of Piperazinediones Derived from 2-Amino-4,7-dialkoxyindan-2-carboxylic Acids

  摘要：

  1,4-Piperazine-2,5-diones possessing C-2h molecular symmetry and bearing four methoxy, ethoxy, butoxy, hexyloxy, octyloxy, nonyloxy, dodecyloxy, or octadecyloxy groups were synthesized from 2-amino-4,7-dialkoxyindan-2-carboxylic acids. Where possible, the piperazinediones were crystallized from appropriate solvents and the supramolecular organizations were determined by X-ray crystallography. In each case so studied, crystal assembly via three mutually orthogonal interactions, namely, R-2(2)(8) hydrogen bonding, arene perpendicular edge-to-center interactions, and alkyl chain interdigitation, was observed. The thermochemical properties of these compounds were studied by modulated differential scanning calorimetry. In most cases, one or more reversible thermal events were observed between room temperature and melting to an isotropic liquid. In the cooling cycle, freezing point temperatures were observed to decrease with increasing hydrocarbon chain length. This may be due to greater entropic penalties for hydrogen-bond association of molecules with longer hydrocarbon chains.

  DOI：

  10.1021/cg301003p
• 作为产物：
  描述：

  1-碘己烷 、 2,3-二甲基氢醌 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 72.33h， 以71%的产率得到1,4-bis(hexyloxy)-2,3-dimethylbenzene
  参考文献：
  名称：

  Organic Crystal Engineering with 1,4-Piperazine-2,5-diones. 8. Synthesis, Crystal Packing, and Thermochemistry of Piperazinediones Derived from 2-Amino-4,7-dialkoxyindan-2-carboxylic Acids

  摘要：

  1,4-Piperazine-2,5-diones possessing C-2h molecular symmetry and bearing four methoxy, ethoxy, butoxy, hexyloxy, octyloxy, nonyloxy, dodecyloxy, or octadecyloxy groups were synthesized from 2-amino-4,7-dialkoxyindan-2-carboxylic acids. Where possible, the piperazinediones were crystallized from appropriate solvents and the supramolecular organizations were determined by X-ray crystallography. In each case so studied, crystal assembly via three mutually orthogonal interactions, namely, R-2(2)(8) hydrogen bonding, arene perpendicular edge-to-center interactions, and alkyl chain interdigitation, was observed. The thermochemical properties of these compounds were studied by modulated differential scanning calorimetry. In most cases, one or more reversible thermal events were observed between room temperature and melting to an isotropic liquid. In the cooling cycle, freezing point temperatures were observed to decrease with increasing hydrocarbon chain length. This may be due to greater entropic penalties for hydrogen-bond association of molecules with longer hydrocarbon chains.

  DOI：

  10.1021/cg301003p

文献信息

• Regioselective Cyclopolymerization of 1,7-Octadiynes
  作者：Stefan Naumann、Jörg Unold、Wolfgang Frey、Michael R. Buchmeiser

  DOI：10.1021/ma201749n

  日期：2011.11.8

  The regioselective cyclopolymerization of two structurally different 1,7-octadiynes, i.e. of 1,4-dihexyloxy-2,3-dipropargylbenzene (M1) and (R,R)/(S,S)-4,5-bis(trimethylsilyloxy)-1,7-octadiyne (M2) has been achieved with the modified Grubbs-Hoveyda-type metathesis initiator Ru(NCO)(2) (IMesH(2))(=CH-(2-(2-PrO)C6H4)) (I1, IMesH(2) = 1,3-dimesitylimidazolidin-2-ylidene) and with a series of Schrock initiators in the presence of quinuclidine, yielding conjugated polymers consisting virtually exclusively of 1,2-cyclohex-1-enylenvinylene units. In contrast to I1, Mo(N-2,6-(2-Pr)(2)C6H3) (CHCMe2Ph)(OCHMe2)(2) (I3) allows for establishing a living polymerization with M2 in the presence of quinuclidine. The structure of the polymers, which represent highly soluble and stable poly(acetylene) analogues, Was confirmed by comparing the C-13 NMR shifts of model compounds with those of the corresponding polymer. Poly(ene)s that are virtually solely based on six-membered repeat units show a bathochromic shift in UV-absorption compared to poly(ene)s based on six- and seven-membered rings.
• A donor-type cyclophane with a strongly bent tetrathiafulvalene unit
  作者：J. Roehrich、K. Muellen

  DOI：10.1021/jo00034a033

  日期：1992.4
• Organic Crystal Engineering with 1,4-Piperazine-2,5-diones. 8. Synthesis, Crystal Packing, and Thermochemistry of Piperazinediones Derived from 2-Amino-4,7-dialkoxyindan-2-carboxylic Acids
  作者：Kirk E. Wells、Robin A. Weatherhead、Francis N. Murigi、Gary S. Nichol、Michael D. Carducci、Hugh D. Selby、Eugene A. Mash

  DOI：10.1021/cg301003p

  日期：2012.10.3

  1,4-Piperazine-2,5-diones possessing C-2h molecular symmetry and bearing four methoxy, ethoxy, butoxy, hexyloxy, octyloxy, nonyloxy, dodecyloxy, or octadecyloxy groups were synthesized from 2-amino-4,7-dialkoxyindan-2-carboxylic acids. Where possible, the piperazinediones were crystallized from appropriate solvents and the supramolecular organizations were determined by X-ray crystallography. In each case so studied, crystal assembly via three mutually orthogonal interactions, namely, R-2(2)(8) hydrogen bonding, arene perpendicular edge-to-center interactions, and alkyl chain interdigitation, was observed. The thermochemical properties of these compounds were studied by modulated differential scanning calorimetry. In most cases, one or more reversible thermal events were observed between room temperature and melting to an isotropic liquid. In the cooling cycle, freezing point temperatures were observed to decrease with increasing hydrocarbon chain length. This may be due to greater entropic penalties for hydrogen-bond association of molecules with longer hydrocarbon chains.