(S)-2--3-methyl-1-butanol | 219703-65-8

• 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: (S)-2--3-methyl-1-butanol
• 英文别名: (S)-2-(N-3-tert-butylsalicylidene)amino-3-methyl-1-butanol；(S)-2-(N-3-tert-butylsalicylidene)-amino-3-methyl-1-butanol
• CAS: 219703-65-8
• 化学式: C₁₆H₂₅NO₂
• 分子量: 263.38
• InChiKey: DKEGNWCUOGYMNV-IREQLNLFSA-N

物化性质

• 熔点：
  57 °C
• 沸点：
  377.109±42.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.005±0.14 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.13
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  52.82
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2-叔丁基苯酚 在 六甲基磷酰三胺 、 乙基溴化镁 、 sodium sulfate 作用下， 以 甲醇 为溶剂， 反应 75.0h， 生成 (S)-2--3-methyl-1-butanol
  参考文献：
  名称：

  Enantioselective trimethylsilylcyanation of some aldehydes catalyzed by chiral Schiff base-titanium alkoxide complexes

  摘要：

  A variety of aldehydes (aromatic, heteroaromatic, alpha,beta-unsaturated, and nonconjugate aliphatic aldehydes) has been trimethylsilylcyanated in highly enantiomeric excess (ee) with a catalyst prepared in situ from titanium tetraisopropoxide [Ti(O-i-Pr)4] and chiral Schiff bases. A remarkable rate enhancement was brought about by the addition of the Schiff base into the titanium alkoxide mediated silylcyanation of aldehydes. The chemical structure of chiral Schiff base-titanium alkoxide complexes is discussed based on their C-13 NMR spectra, field desorption (FD) mass spectra, and molecular weights.

  DOI：

  10.1021/jo00058a037

文献信息

• Asymmetric carboncarbon bond forming reactions catalyzed by chiral Schiff base—titanium alkoxide complexes
  作者：Masahiko Hayashi、Tetsuya Inoue、Yasunori Miyamoto、Nobuki Oguni

  DOI：10.1016/s0040-4020(01)89374-1

  日期：1994.4

  The enantioselective addition of trimethylsilyl cyanide to a variety of aldehydes proceeded by the aid of a catalyst prepared in situ from titanium tetraisopropoxide [Ti(O-i-Pr)4] and chiral Schiff bases and gave the corresponding cyanohydrins in high optical yield (up to 96% e.e.). A remarkable rate enhancement was brought about by the addition of the Schiff base to the titanium alkoxide mediated

  在由四异丙醇钛[Ti（O- i- Pr）4 ]和手性席夫碱原位制备的催化剂的帮助下，将三甲基甲硅烷基氰化物对映选择性加成到各种醛中，从而以高光学收率得到了相应的氰醇（最多到96％ee）。通过将席夫碱加入到钛醇盐介导的醛的甲硅烷基氰化中，可以显着提高速率。该催化剂体系还促进了双烯酮与醛的高度对映选择性反应，这导致形成光学活性的5-羟基-3-氧代酯。
• Process for preparation of 5-hydroxy-3-ketoester derivative and optically active substance thereof
  申请人：UBE INDUSTRIES, LTD.

  公开号：EP0641762A1

  公开（公告）日：1995-03-08

  Disclosed is a process for the preparation of a 5-hydroxy-3-ketoester derivative of the formula: in which R¹ represents an alkyl group, an alkenyl group, an alkynyl group, an aryl group or a heterocyclic group, and R² represents an alkyl group or an aryl group, which comprises causing the reaction of an aldehyde compound of the formula R¹CHO in which R¹ has the meanings as defined above and diketene in the presence of a metal compound selected from a titanium or aluminum compound having at least one group of -OR³ in which R³ represents an alkyl group or an aryl group. Further, a process for the preparation of an optically active substance of the 5-hydroxy-3-ketoester derivative causing the reaction of the above compounds in the presence of the metal compound and optically active Schiff base or a complex compound obtained by reacting the metal compound with the optically active Schiff base, also is disclosed.

  本发明公开了一种制备式 5-羟基-3-酮酯衍生物的工艺： 其中R¹代表烷基、烯基、炔基、芳基或杂环基，R²代表烷基或芳基，其包括使式R¹CHO的醛化合物（其中R¹具有如上定义的含义）和二乙烯在选自钛或铝化合物的金属化合物存在下反应，该金属化合物具有至少一个-OR³基团，其中R³代表烷基或芳基。此外，本发明还公开了一种制备 5-羟基-3-酮酯衍生物的光学活性物质的工艺，该工艺使上述化合物在金属化合物和光学活性席夫碱或金属化合物与光学活性席夫碱反应得到的复合物的存在下发生反应。
• New Chiral Schiff Base as a Tridentate Ligand for Catalytic Enantioselective Addition of Diethylzinc to Aldehydes
  作者：Takanori Tanaka、Yorinobu Yasuda、Masahiko Hayashi

  DOI：10.1021/jo060964u

  日期：2006.9.1

  We have developed new chiral Schiff base catalysts for the enantioselective addition of diethylzinc reagents to aldehydes. The reaction of benzaldehyde with diethylzinc in the presence of 1 mol % of the chiral Schiff base catalyst proceeded to afford 1-phenyl-1-propanol in 96% enantiomeric excess (ee).
• TITANIUM COMPOUND AND METHOD FOR PRODUCING OPTICALLY ACTIVE CYANOHYDRINS
  申请人：Mitsui Chemicals, Inc.

  公开号：EP1806336B1

  公开（公告）日：2009-09-30
• Masahiko Hayashi, Tetsuya Inoue, Yasunori Miyamoto, Nobuki Oguni, Tetrahedron, 50 (1994) N 15, S 4385-4398
  作者：Masahiko Hayashi, Tetsuya Inoue, Yasunori Miyamoto, Nobuki Oguni

  DOI：——

  日期：——