2-(2,3-Dimethylbut-2-enyl)-4-methylphenol | 55630-85-8

• 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: 2-(2,3-Dimethylbut-2-enyl)-4-methylphenol
• CAS: 55630-85-8
• 化学式: C₁₃H₁₈O
• 分子量: 190.285
• InChiKey: OZGBWTQDHPAHHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(2,3-Dimethylbut-2-enyl)-4-methylphenol 生成 2,2,3,6-tetramethyl-chroman
  参考文献：
  名称：

  ROSSINSKIJ A. P.; BUNINA-KRIVORUKOVA L. I.; BALYAN X. V., ZH. ORGAN. XIMII , 1975, 11, HO 11, 2364-2369

  摘要：

  DOI：
• 作为产物：
  描述：

  对甲酚 、 1-氯-2,3-二甲基丁-2-烯 生成 2-(2,3-Dimethylbut-2-enyl)-4-methylphenol
  参考文献：
  名称：

  Rossinskii,A.P. et al., Journal of Organic Chemistry USSR (English Translation), 1975, vol. 11, p. 2409 - 2414

  摘要：

  DOI：

文献信息

• Atropisomeric bisoxazoline ligands with a bridge across the 5,5′-position of biphenyl for asymmetric catalysis
  作者：Feijun Wang、Yong Jian Zhang、Hao Wei、Jiaming Zhang、Wanbin Zhang

  DOI：10.1016/j.tetlet.2007.04.007

  日期：2007.6

  be retained by macro-ring strain produced by 5,5′-linkage of biphenyls even without 6,6′-substituents on biphenyls. The Pd(II)-2d complex as catalyst showed high catalytic activity and enantioselectivity for asymmetric Wacker-type cyclization of allylphenols.

  已经开发了新的阻转异构的双恶唑啉配体2家族，其具有跨联苯的5,5'-位的桥。即使在联苯上没有6,6'-取代基，也可以通过由联苯的5,5'-连接产生的大环应变来保持此类配体的轴向手性。Pd（II）-2d配合物作为催化剂，对烯丙基酚的不对称Wacker型环化反应具有很高的催化活性和对映选择性。
• Chelation-Induced Axially Chiral Palladium Complex System with Tetraoxazoline Ligands for Highly Enantioselective Wacker-Type Cyclization
  作者：Yong Jian Zhang、Feijun Wang、Wanbin Zhang

  DOI：10.1021/jo701469y

  日期：2007.11.1

  A new family of chelation-induced axially chiral palladium complexes by using biphenyl ligands 2 with four identical chiral oxazoline groups at four ortho positions has been developed. Although there is no axial chirality in ligands 2 due to the molecular symmetry, when they chelated with one or two palladium ions, the axial chirality could be induced by destroying the molecular symmetry. Significantly

  通过使用在四个邻位具有四个相同的手性恶唑啉基团的联苯配体2，开发了一个新的螯合诱导的轴向手性钯络合物家族。尽管由于分子对称性而在配体2中没有轴向手性，但是当它们与一个或两个钯离子螯合时，可以通过破坏分子对称性来诱导轴向手性。重要的是，在螯合诱导过程中仅产生一种具有（S）轴构型的非对映体金属配合物。螯合诱导的轴向手性催化体系2c -Pd（CF 3 COO）2 （摩尔比为1：1），在高达99％ee的烯丙基苯酚的Wacker型环化反应中显示出优异的催化活性和对映选择性。
• Highly enantioselective Pd(II)-catalyzed Wacker-type cyclization of 2-allylphenols by use of bisoxazoline ligands with axis-unfixed biphenyl backbone
  作者：Feijun Wang、Yong Jian Zhang、Guoqiang Yang、Wanbin Zhang

  DOI：10.1016/j.tetlet.2007.04.064

  日期：2007.6

  A series of axis-unfixed bisoxazoline ligands with different steric and electronic properties has been synthesized. Due to the different steric interactions, the ligands afforded only one of the two possible diastereomeric Pd(II)-complexes upon metal coordination. The palladium complex (S,aS)-8c showed excellent catalytic activities and enantioselectivities in Wacker-type cyclization of allylphenols with up to 98% ee. (c) 2007 Elsevier Ltd. All rights reserved.
• Cationic Palladium/Boxax Complexes for Catalytic Asymmetric Wacker-Type Cyclization
  作者：Yasuhiro Uozumi、Kazuhiko Kato、Tamio Hayashi

  DOI：10.1021/jo980245i

  日期：1998.7.1

  Catalyticasymmetric Wacker-type cyclization of 2-(2,3-dimethyl-2-butenyl)phenol (la) was efficiently catalyzed by 1 or 2 mol % of a cationic palladium-boxax complex generated in situ by mi;ring Pd(CH3CN)(4)(BF4)(2) with (S,S)-ip-boxax (3a) in the presence of p-benzoquinone to give (S)-(-)-2-isopropenyl-2-methyl-2,3-dihydrobenzofuran (2a) in 94-96% ee and 45-85% yield. An X-ray diffraction study of the crystal structure of Pd(OCOCF3)(2)(S,S)-ip-boxax} (6) revealed that the orientation of alkyl substituents on the borax ligand is perpendicular to the plane of the square planar complex.
• Catalytic Asymmetric Wacker-Type Cyclization
  作者：Yasuhiro Uozumi、Kazuhiko Kato、Tamio Hayashi

  DOI：10.1021/ja9701366

  日期：1997.5.1