(S)-2-methyl-1-(2-methyl-5-pyrimidyl)propan-1-ol | 173068-92-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: (S)-2-methyl-1-(2-methyl-5-pyrimidyl)propan-1-ol
• 英文别名: (1S)-2-methyl-1-(2-methylpyrimidin-5-yl)propan-1-ol
• CAS: 173068-92-3
• 化学式: C₉H₁₄N₂O
• 分子量: 166.223
• InChiKey: KDDKUGKMCOOGIH-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  46
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (S)-2-methyl-1-(2-methyl-5-pyrimidyl)propan-1-ol 以 吡啶 为溶剂， 反应 24.0h， 生成 (S)-(-)-2-methyl-1-(2-methyl-5-pyrimidyl)-1-propyl acetate
  参考文献：
  名称：

  Tanji, Shigehisa; Kodaka, Yasutaka; Shibata, Takanori, Heterocycles, 2000, vol. 52, # 1, p. 151 - 158

  摘要：

  DOI：
• 作为产物：
  描述：

  二异丙基锌 、 2-甲基-5-嘧啶甲醛 在 (S)-2-methyl-1-(2-methyl-5-pyrimidyl)propan-1-ol 作用下， 以 甲苯 为溶剂， 反应 108.0h， 以38%的产率得到(S)-2-methyl-1-(2-methyl-5-pyrimidyl)propan-1-ol
  参考文献：
  名称：

  Highly Enantioselective Catalytic Asymmetric Automultiplication of Chiral Pyrimidyl Alcohol

  摘要：

  DOI：

  10.1021/ja953066g
• 作为试剂：
  描述：

  二异丙基锌 、 2-甲基-5-嘧啶甲醛 在 (S)-2-methyl-1-(2-methyl-5-pyrimidyl)propan-1-ol 作用下， 以 甲苯 为溶剂， 反应 108.0h， 以38%的产率得到(S)-2-methyl-1-(2-methyl-5-pyrimidyl)propan-1-ol
  参考文献：
  名称：

  Highly Enantioselective Catalytic Asymmetric Automultiplication of Chiral Pyrimidyl Alcohol

  摘要：

  DOI：

  10.1021/ja953066g

文献信息

• One-pot asymmetric autocatalytic reaction with remarkable amplification of enantiomeric excess
  作者：Takanori Shibata、Tadakatsu Hayase、Jun Yamamoto、Kenso Soai

  DOI：10.1016/s0957-4166(97)00183-3

  日期：1997.6

  A trace amount (ca. 3 mg) of 2-methylpyrimidyl alkanol with only a slight enantiomeric excess (0.2 – 0.3% e.e.) was auto-multiplied with dramatic amplification of enantiomeric excess (up to ca. 90% e.e.) in one-pot asymmetric autocatalytic reaction using diisopropylzinc and 2-methylpyrimidine-5-carbaldehyde.

  一锅中仅微量（2-约0.3％ee）的痕量（约3 mg）2-甲基嘧啶基烷烃自动倍增，对映体过量（高达约90％ee）急剧扩增二异丙基锌和2-甲基嘧啶-5-甲醛的不对称自催化反应。
• Physical and Chemical Rationalization for Asymmetric Amplification in Autocatalytic Reactions
  作者：Frederic G. Buono、Hiroshi Iwamura、Donna G. Blackmond

  DOI：10.1002/anie.200353086

  日期：2004.4.13
• Amplification of a Slight Enantiomeric Imbalance in Molecules Based on Asymmetric Autocatalysis:  The First Correlation between High Enantiomeric Enrichment in a Chiral Molecule and Circularly Polarized Light
  作者：Takanori Shibata、Jun Yamamoto、Naoko Matsumoto、Shigeru Yonekubo、Shunji Osanai、Kenso Soai

  DOI：10.1021/ja980815w

  日期：1998.11.1
• A Few Molecules Can Control the Enantiomeric Outcome. Evidence Supporting Absolute Asymmetric Synthesis Using the Soai Asymmetric Autocatalysis
  作者：Daniel A. Singleton、Loan K. Vo

  DOI：10.1021/ol035605p

  日期：2003.11.1

  Experiments were carried out to investigate whether the Soai asymmetric autocatalysis can accomplish true absolute asymmetric synthesis. In 54 reactions, R and S enantiomeric products were obtained 27 times each. Of 25 pairs of side-by-side identical reactions, 12 afforded opposite enantiomers. In a test of the mechanistic viability of a random-chance process, it was found that a very few molecules (approximately 60 000) were sufficient to control the enantiomeric outcome of these reactions. These observations appear most consistent with asymmetric synthesis originating from the chance enantiomeric excess in a racemate.
• Highly Enantioselective Catalytic Asymmetric Automultiplication of Chiral Pyrimidyl Alcohol
  作者：Takanori Shibata、Hiroshi Morioka、Tadakatsu Hayase、Kaori Choji、Kenso Soai

  DOI：10.1021/ja953066g

  日期：1996.1.1