4-acetoxy-α-cyanobenzylalcohol | 133412-36-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: 4-acetoxy-α-cyanobenzylalcohol
• 英文别名: (S)-4-Acetyloxy-mandelonitrile；[4-[cyano(hydroxy)methyl]phenyl] acetate
• CAS: 133412-36-9
• 化学式: C₁₀H₉NO₃
• 分子量: 191.186
• InChiKey: XYFHMGVHCBRZGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  70.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-acetoxy-α-cyanobenzylalcohol 、 dihydroartemisinin 生成 β-4-hydroxy-(α-cyano)-benzyl-dihydroartemisinin ether
  参考文献：
  名称：

  ARTEMISINE (QINGHAOSU) DERIVATIVES, THEIR PREPARATION METHODS AND THEIR USE, AND PHARMACEUTICAL COMPOSITIONS CONTAINING THE SAME

  摘要：

  公开号：

  EP1845099B1
• 作为产物：
  描述：

  4-乙酰氧基苯甲醛 在 盐酸 、 1-(3,5-bis(trifluoromethyl)phenyl)-3-((1R,2R)-2-(5-phenyl-1H-imidazol-1-yl)cyclohexyl)thiourea 、 水 、 苯甲酸 作用下， 以 乙酸乙酯 、 甲苯 为溶剂， 反应 19.0h， 生成 4-acetoxy-α-cyanobenzylalcohol
  参考文献：
  名称：

  Cooperative Thiourea–Brønsted Acid Organocatalysis: Enantioselective Cyanosilylation of Aldehydes with TMSCN

  摘要：

  We report a new thiourea-Bronsted acid cooperative catalytic system for the enantioselective cyanosilylation of aldehydes with yields up to 90% and enamioselectivities up to 88%. The addition of an achiral acid was found to be crucial for high asymmetric induction. Mechanistic investigations using a combination of NMR, ESI-MS, and density functional theory computations (including solvent corrections) at the M06/6-31G(d,p) level of theory suggest that the key catalytic species results from the cooperative interaction of bifunctional thioureas and an achiral acid that form well-defined chiral hydrogen-bonding environments.

  DOI：

  10.1021/jo201864e

文献信息

• METHOD FOR PRODUCING OPTICALLY ACTIVE CYANOHYDRIN COMPOUND
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP2264005A1

  公开（公告）日：2010-12-22

  A method of producing an optically active cyanohydrin compound represented by formula (3) (wherein, Q1 and Q2 are as defined below, and * represents that the indicated carbon atom is the optically active center) comprising reacting an aldehyde compound represented by formula (2) (wherein, Q1 and Q2 represent each independently a hydrogen atom, optionally substituted alkyl group having 1 to 6 carbon atoms, or the like) with hydrogen cyanide in the presence of a silyl compound and an asymmetric complex which is obtained by reacting an optically active pyridine compound represented by formula (1) (wherein, R1 and R2 represent each independently a hydrogen atom, alkyl group having 1 to 6 carbon atoms, or the like, provided that R1 and R2 are not the same.) with an aluminum halide.

  一种生产由式（3）表示的光学活性氰醇化合物的方法 (其中，Q1 和 Q2 如下文所定义，* 代表所指示的碳原子是光学活性中心）的方法，包括使式（2）所代表的醛化合物发生反应 (其中，Q1 和 Q2 各自独立地代表氢原子、具有 1 至 6 个碳原子的任选取代的烷基或类似基团）与氰化氢在硅烷基化合物和一种不对称络合物的存在下反应，该不对称络合物是由式（1）所代表的具有光学活性的吡啶化合物反应得到的 (其中，R1 和 R2 各自独立地代表氢原子、具有 1 至 6 个碳原子的烷基或类似基团，但 R1 和 R2 不能相同）与卤化铝反应。
• Artemisinin (Qinghaosu) Derivatives, Their Preparation Methods And Their Use, And Pharmaceutical Compositions Containing The Same
  申请人：Li Ying

  公开号：US20080139642A1

  公开（公告）日：2008-06-12

  The invention provides a type of artemisinin derivatives having following structure I, its preparation method and use, as well as a pharmaceutical composition containing such artemisinin derivatives and its use. The artemisinin derivatives of the present invention and their pharmaceutical composition containing the artemisinin derivatives. have immunosuppressive activities and can be used more safely. The composition which comprises the artemisinin derivatives can be formulated into long-term dosage forms such as tablet, pellet and the like, and have wider productive and use value.
• US7910750B2
  申请人：——

  公开号：US7910750B2

  公开（公告）日：2011-03-22
• US8309753B2
  申请人：——

  公开号：US8309753B2

  公开（公告）日：2012-11-13
• Cooperative Thiourea–Brønsted Acid Organocatalysis: Enantioselective Cyanosilylation of Aldehydes with TMSCN
  作者：Zhiguo Zhang、Katharina M. Lippert、Heike Hausmann、Mike Kotke、Peter R. Schreiner

  DOI：10.1021/jo201864e

  日期：2011.12.2

  We report a new thiourea-Bronsted acid cooperative catalytic system for the enantioselective cyanosilylation of aldehydes with yields up to 90% and enamioselectivities up to 88%. The addition of an achiral acid was found to be crucial for high asymmetric induction. Mechanistic investigations using a combination of NMR, ESI-MS, and density functional theory computations (including solvent corrections) at the M06/6-31G(d,p) level of theory suggest that the key catalytic species results from the cooperative interaction of bifunctional thioureas and an achiral acid that form well-defined chiral hydrogen-bonding environments.