6,6-Dimethylheptane-1,5-diol | 117856-32-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 6,6-Dimethylheptane-1,5-diol
• 英文别名: 6,6-dimethyl-1,5-heptanediol
• CAS: 117856-32-3
• 化学式: C₉H₂₀O₂
• 分子量: 160.257
• InChiKey: BHVNIZRJYXTKHH-UHFFFAOYSA-N

物化性质

• 沸点：
  244.9±8.0 °C(Predicted)
• 密度：
  0.928±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6,6-Dimethylheptane-1,5-diol 在 氯化亚砜 作用下， 反应 168.0h， 以39%的产率得到2-tert-Butyltetrahydropyran
  参考文献：
  名称：

  Ring Closure Reactions of Substituted 4-Pentenyl-1-oxy Radicals. The Stereoselective Synthesis of Functionalized Disubstituted Tetrahydrofurans

  摘要：

  N-(Alkyloxy)pyridine-2( VT)-thiones 3 and benzenesulfenic acid O-esters 5 have been synthesized from substituted 4-pentenols 1 or the derived tosylates. Compounds 3 and 5 are efficient sources of free alkoxy radicals 6 which undergo synthetically useful fast ring closure reactions 6 --> 8 [k(exo) = (2 +/- 1) x 10(8) s(-1) to (6 +/- 2) x 10(9) s(-1) (T = 30 +/- 0.2 degrees C)]. Tetrahydrofurfuryl radicals 8 can be trapped with, e.g., hydrogen or chlorine atom donors to afford either trans- or cis-disubstituted tetrahydrofurans 10 or 12 depending on the substitution pattern of the 4-pentenyloxy radical. Substituted tetrahydropyrans 11 or 13 are formed in the minor 6-endo-trig cyclization. According to the data of competition kinetics, the observed stereoselectivities in free alkoxy radical cyclizations arise from steric interactions between the substituents in the transition state of the ring closure reactions. Alkyl substituents cause small differences in the measured relative rate constants of B-exo cyclizations which are reminiscent of the data obtained from the rearrangements of alkyl-substituted 5-hexenyl radicals. Likewise, a stereochemical model for oxygen radical cyclization is proposed where the pentenyloxy chain adopts a six-membered, chairlike transition state with the alkyl substituents preferentially situated in the pseudoequatorial positions leading to 2,5-trans-, 2,4-cis-, and 2,3-trans-substituted tetrahydrofurfuryl radicals 8 as the major intermediates.

  DOI：

  10.1021/jo00126a021
• 作为产物：
  描述：

  新戊酰基乙酸甲酯 在 氢氧化钾 、 lithium aluminium tetrahydride 、 硫酸 、 sodium ethanolate 作用下， 反应 86.0h， 生成 6,6-Dimethylheptane-1,5-diol
  参考文献：
  名称：

  Ring Closure Reactions of Substituted 4-Pentenyl-1-oxy Radicals. The Stereoselective Synthesis of Functionalized Disubstituted Tetrahydrofurans

  摘要：

  N-(Alkyloxy)pyridine-2( VT)-thiones 3 and benzenesulfenic acid O-esters 5 have been synthesized from substituted 4-pentenols 1 or the derived tosylates. Compounds 3 and 5 are efficient sources of free alkoxy radicals 6 which undergo synthetically useful fast ring closure reactions 6 --> 8 [k(exo) = (2 +/- 1) x 10(8) s(-1) to (6 +/- 2) x 10(9) s(-1) (T = 30 +/- 0.2 degrees C)]. Tetrahydrofurfuryl radicals 8 can be trapped with, e.g., hydrogen or chlorine atom donors to afford either trans- or cis-disubstituted tetrahydrofurans 10 or 12 depending on the substitution pattern of the 4-pentenyloxy radical. Substituted tetrahydropyrans 11 or 13 are formed in the minor 6-endo-trig cyclization. According to the data of competition kinetics, the observed stereoselectivities in free alkoxy radical cyclizations arise from steric interactions between the substituents in the transition state of the ring closure reactions. Alkyl substituents cause small differences in the measured relative rate constants of B-exo cyclizations which are reminiscent of the data obtained from the rearrangements of alkyl-substituted 5-hexenyl radicals. Likewise, a stereochemical model for oxygen radical cyclization is proposed where the pentenyloxy chain adopts a six-membered, chairlike transition state with the alkyl substituents preferentially situated in the pseudoequatorial positions leading to 2,5-trans-, 2,4-cis-, and 2,3-trans-substituted tetrahydrofurfuryl radicals 8 as the major intermediates.

  DOI：

  10.1021/jo00126a021

文献信息

• Arene-catalysed reductive lithiation of tetrahydrofuran: improved synthesis of 1,5-diols
  作者：Diego J. Ramón、Miguel Yus

  DOI：10.1016/s0040-4020(01)88496-9

  日期：1992.1

  The reductive cleavage of tetrahydrofuran at −78°C can be easily achieved by using an excess of lithium powder in the presence of BF3·OEt2 and a catalytic amount (<8%) of an arene (naphthalene, biphenyl, 4,4′- di-tert-butylbiphenyl or anthracene), the best results being obtained with naphthalene. The dianion prepared by this method reacts with carbonyl compounds yielding 1,5-diols.

  通过在BF 3 ·OEt 2和催化量（<8％）的芳烃（萘，联苯，4,4）存在下使用过量的锂粉，可以轻松地在-78°C下四氢呋喃的还原裂解′-二叔丁基联苯或蒽），用萘可获得最佳结果。通过该方法制备的二价阴离子与羰基化合物反应，生成1，5-二醇。
• Procédé de stabilisation de polymères à base de chlorure de polyvinyle et polymères ainsi stabilisés
  申请人：RHONE-POULENC SPECIALITES CHIMIQUES

  公开号：EP0022047A1

  公开（公告）日：1981-01-07

  L'invention concerne des compositions stabilisantes pour polymères à base de chlorure de polyvinyle qui comprennent : - a) au moins un dérivé organique du zinc, - b) aumoins un dérivé organique d'un métal du groupe 2a de la classification périodique, - c) au moins un polyol, - d) au moins un ester de l'acide thioglycolique. Elle concerne également un procédé de stabilisation de polymères à base de chlorure de polyvinyle par de telles compositions stabilisantes ainsi que les polymères stabilisés obtenus. A partir des polymères ainsi stabilisés on obtient des objets conformés incolores et transparents.

  本发明涉及用于聚氯乙烯基聚合物的稳定化组合物，其中包括： - a) 至少一种有机锌衍生物、 - b) 至少一种元素周期表 2a 族金属的有机衍生物、 - c) 至少一种多元醇 - d) 至少一种巯基乙酸酯。 本发明还涉及一种使用此类稳定化组合物稳定聚氯乙烯基聚合物的工艺，以及所获得的稳定化聚合物。 用这种方法稳定的聚合物可制成无色透明的形状物体。
• Procédé de stabilisation de polymères à base de chlorure de vinyle, compositions stabilisantes pour la mise en oeuvre du procédé et polymères ainsi stabilisés
  申请人：RHONE-POULENC CHIMIE

  公开号：EP0090748A1

  公开（公告）日：1983-10-05

  L'invention concerne un procédé de stabilisation de polymères à base de chlorure de polyvinyle consistant dans l'emploi conjoint de: al au moins un dérivé organique du zinc, b) au moins un dérivé organique d'un métal du groupe Ila de la classification périodique des éléments, c) au moins un diester de l'acide thiomalique. Elle concerne également les polymères stabilisés ainsi obtenus. A partir des polymères ainsi stabilisés on obtient des objets conformés incolores et transparents.

  本发明涉及一种以聚氯乙烯为基础的聚合物的稳定化工艺，包括联合使用以下物质： a) 至少一种有机锌衍生物、 b) 至少一种元素周期表 IIa 族金属的有机衍生物、 c) 至少一种硫代苹果酸二酯。 它还涉及由此获得的稳定聚合物。 用这种方法稳定的聚合物可制成无色透明的形状物体。
• 3-Chloropropyl and 4-Chlorobutyl Phenyl Ethers as Sources of 1,3-Dilithiopropane and 1,4-Dilithiobutane:  Sequential Reaction with Carbonyl Compounds
  作者：Francisco Foubelo、Sadiq A. Saleh、Miguel Yus

  DOI：10.1021/jo000039m

  日期：2000.6.1

  The reaction of 3-chloropropyl and 4-chlorobutyl phenyl ethers (1) with lithium powder and a catalytic amount of DTBB (5% molar) in THF at -78 degrees C followed by successive treatment with a carbonyl compound [(RRCO)-R-1-C-2 = (BuCHO)-C-t, Me2CO, (CH2)(5)CO, (-)-menthone] at -78 to 20 degrees C and, after 1.5 h at this temperature, with a second one [(RRCO)-R-3-C-4 = (BuCHO)-C-t, PhCHO, Me2CO, MeCOPrn, (CH2)(5)CO, (-)-menthone] at -78 degrees C leads,after hydrolysis with water, to the corresponding 1,5- and 1,6-diols (2). Because of the competition of two different reductive cleavages, 1,4- and 1,5-diols 3 were also obtained as side-reaction products.
• Acetylation of unsymmetrical diols in the presence of Al2O3
  作者：Gary W. Breton、Melissa J. Kurtz、Sharyn L. Kurtz

  DOI：10.1016/s0040-4039(97)00756-9

  日期：1997.6

  The effect of the presence of chromatographic grade Al2O3 on the acetylation of a series of unsymmetrical 1,5-diols was investigated. For diols containing both a primary and a secondary hydroxyl group, it was observed that higher yields of the more hindered secondary acetates were formed in the presence of Al2O3 than the corresponding reactions in solution. (C) 1997 Elsevier Science Ltd.