p-cresol-3,5-d2-OH | 2213-77-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: p-cresol-3,5-d2-OH
• 英文别名: 3,5-d₂-p-cresol；2,6-Dideutero-4-hydroxytoluol；3,5-Dideuterio-p-kresol；3,5-dideuterio-4-methyl-phenol
• CAS: 2213-77-6
• 化学式: C₇H₈O
• 分子量: 110.124
• InChiKey: IWDCLRJOBJJRNH-PBNXXWCMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  8.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  p-cresol-3,5-d2-OH 、 2-丙炔-1-醇 在 phenyliodine(III) diacetate 作用下， 以37%的产率得到4-methyl-4-(prop-2-yn-1-yloxy)cyclohexa-2,5-dien-1-one-3,5-d₂
  参考文献：
  名称：

  Tunable Arylative Cyclization of 1,6-Enynes Triggered by Rhodium(III)-Catalyzed C–H Activation

  摘要：

  Two tunable arylative cyclizations of cyclohexadienone-containing 1,6-enynes are reported via rhodium(III)-catalyzed C-H activation of O-substituted N-hydroxybenzamides. The use of different O substituents, i.e. O-Piv and O-Me, on the directing group allows the formation of either tetracyclic isoquinolones through an (c)-Michael addition process or hydrobenzofurans through a (N)Michael addition process. Mechanistic investigations of these two cascade reactions clearly indicated that the C-H bond cleavage process was involved in the turnover-limiting step. Furthermore, the cyclization products could be subjected to various transformations for elaborating the pharmaceutically and synthetically valuable potential. This is the first example of a rhodium(III)-catalyzed arylative cyclization reaction of 1,6-enynes, and the results extend the application realm of Cp*Rh-III-catalyzed C-H activation cascade reactions.

  DOI：

  10.1021/ja5072702
• 作为产物：
  描述：

  2,3,5,6-d4-p-cresol 在 硫酸 、 水 作用下， 反应 20.0h， 以49%的产率得到p-cresol-3,5-d2-OH
  参考文献：
  名称：

  Tunable Arylative Cyclization of 1,6-Enynes Triggered by Rhodium(III)-Catalyzed C–H Activation

  摘要：

  Two tunable arylative cyclizations of cyclohexadienone-containing 1,6-enynes are reported via rhodium(III)-catalyzed C-H activation of O-substituted N-hydroxybenzamides. The use of different O substituents, i.e. O-Piv and O-Me, on the directing group allows the formation of either tetracyclic isoquinolones through an (c)-Michael addition process or hydrobenzofurans through a (N)Michael addition process. Mechanistic investigations of these two cascade reactions clearly indicated that the C-H bond cleavage process was involved in the turnover-limiting step. Furthermore, the cyclization products could be subjected to various transformations for elaborating the pharmaceutically and synthetically valuable potential. This is the first example of a rhodium(III)-catalyzed arylative cyclization reaction of 1,6-enynes, and the results extend the application realm of Cp*Rh-III-catalyzed C-H activation cascade reactions.

  DOI：

  10.1021/ja5072702

文献信息

• Aromatic hydroxylation by oxygen (3P) atoms
  作者：Setsuo Takamuku、Hiroyuki Matsumoto、Akira Hori、Hiroshi Sakurai

  DOI：10.1021/ja00524a047

  日期：1980.2
• Vibrational spectra and normal coordinate analysis of p-cresol and its deuterated analogs
  作者：Hideo Takeuchi、Noriko Watanabe、Issei Harada

  DOI：10.1016/0584-8539(88)80138-7

  日期：1988.1