(6-tert-butyl-2,2-dimethyl-4H-benzo[1,3]dioxin-8-yl)-methanol | 206879-68-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: (6-tert-butyl-2,2-dimethyl-4H-benzo[1,3]dioxin-8-yl)-methanol
• 英文别名: (6-tert-butyl-2,2-dimethyl-4H-1,3-benzodioxin-8-yl)methanol
• CAS: 206879-68-7
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: VCYALDWWLONQFY-UHFFFAOYSA-N

物化性质

• 沸点：
  352.5±42.0 °C(Predicted)
• 密度：
  1.055±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (6-tert-butyl-2,2-dimethyl-4H-benzo[1,3]dioxin-8-yl)-methanol 在 高氯酸 、 四溴化碳 、 水 、 sodium hydride 、 三苯基膦 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 20.83h， 生成 p-(tert-butyl)hexahomotrioxacalix[3]arene
  参考文献：
  名称：

  Stepwise Construction of Some Hexahomooxacalix[3]arenes and Their Conformations in Solid State

  摘要：

  Hexahomooxacalix[3]arenes 1 bearing different substituents on their upper rim were synthesized from the corresponding Linear trimers 2 by the acid-catalyzed cyclization. The X-ray crystallographic analyses of 1 (R-1 = R-3 = H, R-2 = t-Bu, and R-1 = Et, R-2 = t-Bu, R-3 = i-Pr) revealed that they adopt a cone conformation, owing to an intramolecular hydrogen-bonded network in the solid state.

  DOI：

  10.1021/jo971945a
• 作为产物：
  描述：

  4-叔-丁基-2,6-二(羟基甲基)苯酚 、 2,2-二甲氧基丙烷 在 对甲苯磺酸 作用下， 以 丙酮 为溶剂， 反应 3.0h， 以86%的产率得到(6-tert-butyl-2,2-dimethyl-4H-benzo[1,3]dioxin-8-yl)-methanol
  参考文献：
  名称：

  Stepwise Construction of Some Hexahomooxacalix[3]arenes and Their Conformations in Solid State

  摘要：

  Hexahomooxacalix[3]arenes 1 bearing different substituents on their upper rim were synthesized from the corresponding Linear trimers 2 by the acid-catalyzed cyclization. The X-ray crystallographic analyses of 1 (R-1 = R-3 = H, R-2 = t-Bu, and R-1 = Et, R-2 = t-Bu, R-3 = i-Pr) revealed that they adopt a cone conformation, owing to an intramolecular hydrogen-bonded network in the solid state.

  DOI：

  10.1021/jo971945a

文献信息

• Mechanism and scope of salen bifunctional catalysts in asymmetric aldehyde and α-ketoester alkylation
  作者：Michael W. Fennie、Erin F. DiMauro、Erin M. O'Brien、Venkatachalam Annamalai、Marisa C. Kozlowski

  DOI：10.1016/j.tet.2005.03.117

  日期：2005.6

  complexes of C2-symmetric Lewis acid/Lewis base salen ligands provide bifunctional activation resulting in rapid rates in the enantioselective addition of diethylzinc to aldehydes (up to 92% ee). Further experiments probed the reactivity of the individual Lewis acid and Lewis base components of the catalyst and established that both moieties are essential for asymmetric catalysis. These catalysts are also

  C 2对称的路易斯酸/路易斯碱塞伦配体的金属配合物提供双功能激活，从而使二乙基锌对醛的对映选择性加成速率加快（最高ee为92％）。进一步的实验探查了催化剂中各个路易斯酸和路易斯碱组分的反应性，并确定这两个部分对于不对称催化都是必不可少的。这些催化剂在将二乙基锌不对称加成到α-酮酸酯中也是有效的。这一发现意义重大，因为单独的α-酮酸酯充当其自身的配体，以加速Et 2的外消旋1,2-羰基加成反应锌与外消旋羰基还原。后者通过金属茂途径进行，并且通常占主要产物。奇异的路易斯酸催化剂不能在这两个竞争路径上加速对映选择性的1，2-加成。然而，双官能氨基塞伦催化剂以优异的收率，完全的化学选择性和良好的对映选择性（高达88％ee）快速提供对映体富集的1,2-加成产物。合成了双功能氨基塞隆的文库，并在该反应中进行了评估。已经在鸦片拮抗剂的合成中证明了α-酮酸酯方法的实用性。
• Salen-Derived Catalysts Containing Secondary Basic Groups in the Addition of Diethylzinc to Aldehydes
  作者：Erin F. DiMauro、Marisa C. Kozlowski

  DOI：10.1021/ol016535u

  日期：2001.9.1

  bifunctional salen catalysts which contain Lewis acid and Lewis base activating groups is described. These groups can be altered independently to control nucleophilic and electrophilic activation of the reacting substrates. These salen-derived catalysts show enhanced reactivity in the addition of diethylzinc to aldehydes with respect to most other salen, amino alcohol, and diamine derived catalysts and reactivity

  描述了一组含有路易斯酸和路易斯碱活化基团的模块式双功能萨伦催化剂。这些基团可以独立地改变以控制反应底物的亲核和亲电子活化。与大多数其他塞伦，氨基醇和二胺衍生的催化剂相比，这些塞伦衍生的催化剂在将二乙基锌添加到醛中时显示出增强的反应性，并且其反应性可与双磺酰胺和二醇的钛配合物相比。结构：见文字。
• The '2+1' Construction of Homooxacalix[3]arenes Possessing Different Substituents on Their Upper Rims.
  作者：Kazunori TSUBAKI、Koichiro MUKOYOSHI、Tadamune OTSUBO、Kaoru FUJI

  DOI：10.1248/cpb.48.882

  日期：——

  Several homoxacalix[3]arenes possessing different substituents on their upper rims were synthesized in yields of 7-20% by a condensation reaction between the p-substituted phenol dimer and monomer under acidic high-dilution conditions.

  在酸性高稀释条件下，通过对取代苯酚二聚体和单体之间的缩合反应，合成了几种上缘具有不同取代基的均二十碳六[3]烷，收率为 7-20%。
• Modification of the Upper Rim of Homooxacalix[3]arenes and Complexation between a Nitrohomooxacalix[3]arene Derivative and <i>n</i>-Hexylamine
  作者：Kazunori Tsubaki、Tadamune Otsubo、Tatsuya Morimoto、Hiromi Maruoka、Mika Furukawa、Yashima Momose、Muhong Shang、Kaoru Fuji

  DOI：10.1021/jo026152p

  日期：2002.11.1

  Several functional groups were introduced on the upper rim of (lower rim free) homooxacalix[3]arene for the first time. The swinging nitrohomooxacalix[3]arene host 1 was fixed in the cone conformation by complexation with n-hexylamine.