O-acetyl-(S)-2-hydroxyheptanonitrile | 139894-61-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: O-acetyl-(S)-2-hydroxyheptanonitrile
• 英文别名: (S)-(-)-1-cyanohexyl acetate；(R)-1-cyanohexyl acetate；(S)-2-acetoxyheptanenitrile；[(1S)-1-cyanohexyl] acetate
• CAS: 139894-61-4
• 化学式: C₉H₁₅NO₂
• 分子量: 169.224
• InChiKey: HYRBUECMEDAHLK-VIFPVBQESA-N

物化性质

• 沸点：
  250.6±13.0 °C(Predicted)
• 密度：
  0.970±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  O-acetyl-2-hydroxy-2-pentylacetonitrile 生成 O-acetyl-(S)-2-hydroxyheptanonitrile
  参考文献：
  名称：

  Ohta, Hiromichi; Hiraga, Satoshi; Miyamoto, Kenji, Agricultural and Biological Chemistry, 1988, vol. 52, # 12, p. 3023 - 3028

  摘要：

  DOI：

文献信息

• Enantioselective cyanosilylation of aldehydes catalyzed by novel camphor derived Schiff bases-titanium(IV) complexes
  作者：Ewelina Błocka、Mariusz J. Bosiak、Mirosław Wełniak、Agnieszka Ludwiczak、Andrzej Wojtczak

  DOI：10.1016/j.tetasy.2014.03.001

  日期：2014.4

  Five tridentate Schiff bases have been prepared from (1R,2S,3R,4S)-3-amino-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol and salicylaldehydes. X-ray structure investigation revealed differences in their molecular conformation, and their titanium(IV) complexes have been studied with NMR techniques. Among them the complex with the Schiff base obtained from 2-hydroxy-3-isopropylbenzaldehyde, is the most selective

  五三齿席夫碱已经从（1制备- [R，2小号，3 - [R，4小号）-3-氨基- 1,7,7-三甲基二环[2.2.1]庚-2-醇和水杨醛。X射线结构的调查显示在它们的分子构象的差异，和它们的钛（IV）络合物进行了研究NMR技术。它们之间的复合物与由2-羟基-3-异丙基苯甲醛得到的席夫碱，为脂肪族，脂环族，芳族，杂芳族和醛的硅氰化反应最有选择性的催化剂。最高的对映选择性，> 99％时，在加入三甲基氰硅烷的给肉桂醛实现。
• Enantioselective O-acetylcyanation/cyanoformylation of aldehydes using catalysts with built-in crown ether-like motif in chiral macrocyclic V(V) salen complexes
  作者：Noor-ul H. Khan、Arghya Sadhukhan、Nabin C. Maity、Rukhsana I. Kureshy、Sayed H.R. Abdi、S. Saravanan、Hari C. Bajaj

  DOI：10.1016/j.tet.2011.07.005

  日期：2011.9

  bis-aldehydes 2 and 3 were synthesized and used as efficient catalysts in asymmetric cyanation reactions. The V(V) catalysts demonstrated excellent performance (product yields and ees up to 99%) with potassium cyanide (KCN) and sodium cyanide (NaCN). The catalytic system also performed very well with a safer source of cyanide-ethyl cyanoformate to give cyanohydrin carbonates in excellent yield and ee (up

  通过1 R，2 R -（-）二氨基环己烷/（1 R，2 R）-（+）-1,2-二苯基乙二胺与双的反应获得的大环配体衍生的手性大环V（V）salen络合物1a – f合成了2-醛2和3-醛，并将其用作不对称氰化反应的有效催化剂。V（V）催化剂与氰化钾（KCN）和氰化钠（NaCN）一起表现出出色的性能（产品收率和ee高达99％）。使用更安全的氰化物-氰基甲酸乙酯源，该催化体系的性能也非常好，从而以优异的收率和ee（高达97％）得到氰醇碳酸盐。V（V）大环Salen络合物1b保持其在多克水平的性能，并方便地回收了许多次。
• Dual Lewis Acid−Lewis Base Activation in Enantioselective Cyanation of Aldehydes Using Acetyl Cyanide and Cyanoformate as Cyanide Sources
  作者：Stina Lundgren、Erica Wingstrand、Maël Penhoat、Christina Moberg

  DOI：10.1021/ja052804q

  日期：2005.8.24

  Dual activation by a chiral Lewis acid and an achiral or chiral Lewis base enabled cyanation of both aromatic and aliphatic aldehydes with acetyl cyanide and ethyl cyanoformate to provide direct access to O-acetylated and O-alkoxycarbonylated cyanohydrins, respectively, under mild conditions. With a combination of a Ti-salen catalyst and Et3N, benzaldehyde was converted to the O-acetylated cyanohydrin

  手性路易斯酸和非手性或手性路易斯碱的双重活化能够使芳香族和脂肪族醛与乙酰氰和氰基甲酸乙酯在温和条件下直接获得 O-乙酰化和 O-烷氧基羰基化的氰醇。使用 Ti-salen 催化剂和 Et3N 的组合，苯甲醛在 -40 摄氏度的 10 小时内以 89% 的分离产率转化为 94% ee 的 O-乙酰化氰醇。
• Enantioselective Synthesis of Aliphatic Cyanohydrin Acetates
  作者：Ulf Hanefeld、Lars Veum

  DOI：10.1055/s-2005-872671

  日期：——

  When the standard conditions for the enantioselective synthesis of cyanohydrin acetates via dynamic kinetic resolution are applied to aliphatic substrates, only a kinetic resolution is observed. However, by exchanging the base (Amberlite) against NaCN, quantitative conversions and good enantioselectivities are obtained.

  将动态动力学分辨法制备氰醇醋酸盐的非对映选择性合成标准条件应用于脂肪族底物时，仅观察到动力学分辨。然而，通过将（Amberlite）交换为NaCN，可以获得定量转化和良好的非对映选择性。
• One-Pot Synthesis of Optically Active Cyanohydrin Acetates from Aldehydes via Quinidine-Catalyzed Transhydrocyanation Coupled with Lipase-Catalyzed Kinetic Resolution in Organic Solvent
  作者：Minoru Inagaki、Akihiko Hatanaka、Mitsuo Mimura、Jun Hiratake、Takaaki Nishioka、Jun’ichi Oda

  DOI：10.1246/bcsj.65.111

  日期：1992.1

  transhydrocyanation allows for in situ racemization of the unreacted cyanohydrins and concurrent kinetic resolution by lipase enabled the preparation of (S)-3b–d with 40–82% e.e. in more than 50% yield. Polymer-supported cinchona alkaloid was also used as a catalyst for this one-pot reaction and showed the comparable chemical and optical yield to that for the soluble monomeric alkaloid. The insoluble polymer and lipase

  开发了一种新的一锅合成方法来制备旋光氰醇乙酸酯。通过奎尼丁催化的氢氰化反应从醛和丙酮氰醇中生成外消旋氰醇，然后使用乙酸异丙烯酯作为酰化剂，通过脂肪酶以立体选择性方式将所得氰醇 2a-j 乙酰化。多种醛 1a-j 成功地转化为相应的氰醇乙酸酯 3a-j，其 ee 为 47-95%，而没有分离不稳定的氰醇 2。此外，碱催化转移氢氰化的可逆性质允许未反应的氰醇原位外消旋化脂肪酶同时进行动力学拆分使 (S)-3b-d 能够以 50% 以上的产率制备 40-82% ee 的 (S)-3b-d。聚合物负载的金鸡纳生物碱也被用作这种一锅反应的催化剂，并显示出与可溶性单体生物碱相当的化学和光学产率。不溶性聚合物和脂肪酶...