1-anthryl tert-butyl ketone | 109690-73-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-anthryl tert-butyl ketone
• 英文别名: 1-[1]anthryl-2,2-dimethyl-propan-1-one；1-[1]Anthryl-2,2-dimethyl-propan-1-on；1-(Anthracen-1-YL)-2,2-dimethylpropan-1-one；1-anthracen-1-yl-2,2-dimethylpropan-1-one
• CAS: 109690-73-5
• 化学式: C₁₉H₁₈O
• 分子量: 262.351
• InChiKey: VOPABCOGHFNZKP-UHFFFAOYSA-N

物化性质

• 沸点：
  425.8±14.0 °C(Predicted)
• 密度：
  1.098±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-anthryl tert-butyl ketone 在 盐酸 、 dimethyl sulfide borane 、 (S)-tetrahydro-1-butyl-3,3-diphenyl-1H,3H-pyrrolo{2,1-c}{1,3,2}oxazaborole 作用下， 生成 (S)-1-anthryl-tert-butylcarbinol
  参考文献：
  名称：

  Kinetic Resolution by Enantioselective Dihydroxylation of Secondary Allylic 4-Methoxybenzoate Esters Using a Mechanistically Designed Cinchona Alkaloid Catalyst

  摘要：

  The OsO4-cinchona alkaloid catalyzed asymmetric dihydroxylation process has been applied successfully to the kinetic resolution of 1-substituted allylic alcohols by the use of the 4-methoxybenzoyl derivatives in conjunction with the specifically designed DHQD-PYDZ(S)-anthryl catalyst (5 . OsO4). Thus, (+/-)-3-buten-2-yl 4-methoxybenzoate (4a) and (+/-)-1-phenyl-2-propen-1-yl 4-methoxybenzoate (4b) have been kinetically resolved with relative rate constants of 20 and 79, respectively. These values are among the best reported for the kinetic resolution of racemic compounds using non-enzymatic catalyst systems. The design of this resolution process was accomplished under mechanistic guidance using the transition state model proposed recently for the asymmetric dihydroxylation process. The specially selected ligand 5 possesses a deep U-shaped binding pocket with both the methoxyquinoline and the 1-anthryl walls projecting rearward of the pyridazine linker group at the floor. This catalyst not only recognizes the 4-methoxybenzoyl group of these substrates, which extends into the distant binding pocket of the catalyst, but also provides an open space adjacent to one of the allylic alpha-substituents of the substrate which allows for enantiomeric selection in the dihydroxylation. The magnitude of the kinetic resolution and the absolute stereopreference for the dihydroxylation reaction provide strong evidence for the guiding mechanistic model. The utility of this process is clearly demonstrated by the selective dihydroxylation of 1,4-pentadien-3-yl 4-methoxybenzoate (10) to give diol 11 in 70% isolated yield with >98% ee and >96% de.

  DOI：

  10.1021/ja00149a004
• 作为产物：
  描述：

  1-蒽甲酸 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 1-anthryl tert-butyl ketone
  参考文献：
  名称：

  机械设计的单金鸡纳生物碱是烯烃对映选择性二羟基化的极佳催化剂

  摘要：

  根据最近提出的关于OsO 4促进的由双金鸡纳生物碱衍生物（例如1）催化的烯烃的二羟基化中对映选择性的起源的想法，特别是有强有力的证据证明通过过渡态组装体2可以进行反应，单奎尼丁衍生物3是被选为有前途的催化配体。由3促进的高对映选择性的实验观察提供了有利于过渡态2的其他证据。

  DOI：

  10.1016/s0040-4039(00)78237-2

文献信息

• A mechanistically designed mono-cinchona alkaloid is an excellent catalyst for the enantioselective dihydroxylation of olefins
  作者：E.J. Corey、Mark C. Noe、Michael J. Grogan

  DOI：10.1016/s0040-4039(00)78237-2

  日期：1994.8

  advanced regarding the origin of enantioselectivity in the OsO4-promoted dihydroxylation of olefins catalyzed by bis-cinchona alkaloid derivatives such as 1, specifically strong evidence for reaction via transition state assembly 2, the mono-quinidine derivative 3 was selected as a promising catalytic ligand. The experimental observation of high enantioselectivity promoted by 3 provides additional

  根据最近提出的关于OsO 4促进的由双金鸡纳生物碱衍生物（例如1）催化的烯烃的二羟基化中对映选择性的起源的想法，特别是有强有力的证据证明通过过渡态组装体2可以进行反应，单奎尼丁衍生物3是被选为有前途的催化配体。由3促进的高对映选择性的实验观察提供了有利于过渡态2的其他证据。
• Martynoff, Bulletin de la Societe Chimique de France, 1958, p. 164,173
  作者：Martynoff

  DOI：——

  日期：——
• Kinetic Resolution by Enantioselective Dihydroxylation of Secondary Allylic 4-Methoxybenzoate Esters Using a Mechanistically Designed Cinchona Alkaloid Catalyst
  作者：E. J. Corey、Mark C. Noe、Angel Guzman-Perez

  DOI：10.1021/ja00149a004

  日期：1995.11

  The OsO4-cinchona alkaloid catalyzed asymmetric dihydroxylation process has been applied successfully to the kinetic resolution of 1-substituted allylic alcohols by the use of the 4-methoxybenzoyl derivatives in conjunction with the specifically designed DHQD-PYDZ(S)-anthryl catalyst (5 . OsO4). Thus, (+/-)-3-buten-2-yl 4-methoxybenzoate (4a) and (+/-)-1-phenyl-2-propen-1-yl 4-methoxybenzoate (4b) have been kinetically resolved with relative rate constants of 20 and 79, respectively. These values are among the best reported for the kinetic resolution of racemic compounds using non-enzymatic catalyst systems. The design of this resolution process was accomplished under mechanistic guidance using the transition state model proposed recently for the asymmetric dihydroxylation process. The specially selected ligand 5 possesses a deep U-shaped binding pocket with both the methoxyquinoline and the 1-anthryl walls projecting rearward of the pyridazine linker group at the floor. This catalyst not only recognizes the 4-methoxybenzoyl group of these substrates, which extends into the distant binding pocket of the catalyst, but also provides an open space adjacent to one of the allylic alpha-substituents of the substrate which allows for enantiomeric selection in the dihydroxylation. The magnitude of the kinetic resolution and the absolute stereopreference for the dihydroxylation reaction provide strong evidence for the guiding mechanistic model. The utility of this process is clearly demonstrated by the selective dihydroxylation of 1,4-pentadien-3-yl 4-methoxybenzoate (10) to give diol 11 in 70% isolated yield with >98% ee and >96% de.