(S)-2-N-(salicylideneamino)-3-methyl-butan-1-ol | 916518-81-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (S)-2-N-(salicylideneamino)-3-methyl-butan-1-ol
• 英文别名: (S)-2-(N-salicylidene)amino-3-methyl-1-butanol；(S)-2-(N-salicylideneamino)-3-methyl-1-butanol；(S)-2-(N-(salicylidene)amino)-3-methyl-1-butanol
• CAS: 916518-81-5
• 化学式: C₁₂H₁₇NO₂
• 分子量: 207.272
• InChiKey: VBCNMRKIPUOCEP-ZTFCMROMSA-N

物化性质

• 熔点：
  104-106 °C
• 沸点：
  340.6±27.0 °C(Predicted)
• 密度：
  1.06±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.83
• 重原子数：
  15.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  52.82
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-2-N-(salicylideneamino)-3-methyl-butan-1-ol 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以0.157 g的产率得到2-[(2'-hydroxybenzyl)amino]-3-methyl-1-butanol
  参考文献：
  名称：

  钛-N-水杨基-β-氨基醇配合物催化的高度对映选择性斯特雷克反应

  摘要：

  合成了N-水杨基-β-氨基醇1并作为催化不对称Strecker反应的配体进行了评估。在10摩尔％的Ti- 1配合物的存在下，衍生自芳族和脂族醛的N-苯甲基乙二胺与TMSCN反应，以优异的收率和高达> 98％ee的浓度获得Strecker产品。质子添加剂的存在对于确保良好的转化率和反应速率至关重要。反应条件简单，并且根据配体的构型可以预测其立体化学结果，所述配体的两个对映体均易于合成。

  DOI：

  10.1016/j.tet.2004.07.097
• 作为产物：
  描述：

  L-缬氨醇 、 水杨醛 在 sodium sulfate 作用下， 以 甲醇 为溶剂， 以94%的产率得到(S)-2-N-(salicylideneamino)-3-methyl-butan-1-ol
  参考文献：
  名称：

  手性席夫碱-钛醇盐配合物催化的不对称碳碳键形成反应

  摘要：

  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。

  DOI：

  10.1016/s0040-4020(01)89374-1

文献信息

• Process for preparation of 5-hydroxy-3-ketoester derivative and
  申请人：Ube Industries Ltd.

  公开号：US05457225A1

  公开（公告）日：1995-10-10

  Disclosed is a process for the preparation of a 5-hydroxy-3-ketoester derivative of the formula: ##STR1## in which R.sup.1 represents an alkyl group, an alkenyl group, an alkynyl group, an aryl group or a heterocyclic group, and R.sup.2 represents an alkyl group or an aryl group, which comprises causing the reaction of an aldehyde compound of the formula R.sup.1 CHO in which R.sup.1 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 --OR.sup.3 in which R.sup.3 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.

  披露了一种制备5-羟基-3-酮酯衍生物的工艺，该衍生物的公式为：##STR1##，其中R.sup.1代表烷基、烯基、炔基、芳基或杂环基，R.sup.2代表烷基或芳基，该工艺包括使上述定义的R.sup.1的甲醛化合物R.sup.1 CHO与二酮烯在至少含有一个--OR.sup.3基团的钛或铝化合物存在下发生反应，其中R.sup.3代表烷基或芳基。另外，还披露了一种在金属化合物和光学活性Schiff碱或通过金属化合物与光学活性Schiff碱反应得到的配合物存在下，通过使上述化合物发生反应来制备5-羟基-3-酮酯衍生物的光学活性物质的工艺。
• Substituent effects and mechanism elucidation of enantioselective sulfoxidation catalyzed by vanadium Schiff base complexes
  作者：Qingle Zeng、Heqing Wang、Wen Weng、Wenshi Lin、Yuxing Gao、Xiantong Huang、Yufen Zhao

  DOI：10.1039/b505237h

  日期：——

  The effects of substituents of the Schiff base ligands on oxovanadium-catalyzed enantioselective sulfoxidation were first systematically studied, and a rational mechanism of enantioselective sulfoxidation based on our experimental data and the reported data is proposed.

  首先系统地研究了席夫碱配体的取代基对氧钒钛催化的对映选择性硫氧化的影响，并基于我们的实验数据和报道的数据，提出了对映选择性硫氧化的合理机理。
• Chiral Ti(IV) complexes of hexadentate Schiff bases as precatalysts for the asymmetric addition of TMSCN to aldehydes and the ring opening of cyclohexene oxide
  作者：Yuri N. Belokon、Denis Chusov、Dmitry A. Borkin、Lidia V. Yashkina、Andrey V. Dmitriev、Dmitry Katayev、Michael North

  DOI：10.1016/j.tetasy.2006.08.009

  日期：2006.9

  Chiral dinuclear titanium(IV) complexes (generated in situ from hexadentate Schiff bases and titanium tetra-isopropoxide) have been found to be more effective catalysts for the asymmetric addition of trimethylsilyl cyanide to aldehydes and the ring opening of cyclohexene oxide than their mononuclear analogues. The best results were obtained for benzaldehyde (86% enantiomeric excess) and cyclohexene

  已发现手性二核钛（IV）配合物（由六齿席夫碱和四异丙氧基钛原位生成）比单核类似物更有效地催化三甲基甲硅烷基氰化物不对称加成到醛和环己烯氧化物的开环。苯甲醛（对映体过量86％）和氧化环己烯（对映体过量89％）获得了最佳结果。
• Vanadium-Catalyzed Enantioselective Sulfoxidation and Concomitant, Highly Efficient Kinetic Resolution Provide High Enantioselectivity and Acceptable Yields of Sulfoxides
  作者：Qingle Zeng、Heqing Wang、Tongjian Wang、Yimin Cai、Wen Weng、Yufen Zhao

  DOI：10.1002/adsc.200505259

  日期：2005.12

  facilely prepared and used in enantioselective sulfoxidation. Both the amount of aqueous H2O2 and reaction time greatly influenced the ee values and yields of chiral sulfoxides. High enantioselectivities (up to 99% ee) and reasonable yields (>40%) for various chiral sulfoxides were achieved by combining enantioselective sulfoxidation and appropriate concomitant kinetic resolution.

  简单，便宜，预制的钒-席夫碱络合物易于制备，并用于对映选择性的硫氧化反应。H 2 O 2水溶液的量和反应时间都极大地影响了ee值和手性亚砜的产率。通过将对映选择性磺化氧化和适当的伴随动力学拆分相结合，可以获得各种手性亚砜的高对映选择性（高达ee的99％）和合理的收率（> 40％）。
• 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。