[(2S)-1-hydroxypentan-2-yl] benzoate | 1170725-45-7

• 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: [(2S)-1-hydroxypentan-2-yl] benzoate
• CAS: 1170725-45-7
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: HCFLIGQVRNAQMG-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-benzoyloxyvaleraldehyde 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.33h， 以98%的产率得到[(2S)-1-hydroxypentan-2-yl] benzoate
  参考文献：
  名称：

  Organocatalytic α-oxybenzoylation of aldehydes

  摘要：

  A simple method for the asymmetric alpha-oxybenzoylation of aldehydes is presented. Treatment of a series of aldehydes with benzoyl peroxide in the presence of a MacMillan imidazolidinone leads directly to the alpha-oxybenzoylated product with excellent levels of asymmetric induction. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.03.082

文献信息

• 2-(1-ACYLOXYPENTYL) BENZOIC ACID SALT FORMED BY BASIC AMINO ACID OR AMINOGUANIDINE, PREPARATION METHOD THEREFOR AND USES THEREOF
  申请人：China Pharmaceutical University

  公开号：EP3838887A1

  公开（公告）日：2021-06-23

  The present disclosure discloses salts formed by 2-(1-acyloxy-n-pentyl)benzoic acid and basic amino acid or aminoguanidine, a preparation method thereof, pharmaceutical preparations containing these salts, and application thereof in preparation of drugs for preventing or treating ischemic cardiovascular and cerebrovascular diseases, resisting thrombosis and improving cardio-cerebral circulation disorders. The compound of the present disclosure has excellent water solubility, aqueous solution stability and pharmacokinetic properties, also has significant anti-platelet aggregation, anti-thrombosis, anti-cerebral ischemia and neuroprotective activity. The compound of the present disclosure has significantly better effects than those of (S)-butylphthalide and potassium (R/S)-2-(1-hydroxy-n-pentyl) benzoate (PHPB), has significantly lower acute toxicity to mice by intravenous injection than that of butylphthalide and PHPB, has a lower inhibition rate of the hERG potassium channel in CHO-hERG cells than that of (S)-butylphthalide, and has a negative result in Bacterial Reverse Mutation Test (Ames test).

  本发明公开了2-(1-乙酰氧基-n-戊基)苯甲酸与碱性氨基酸或氨基胍形成的盐、其制备方法、含有这些盐的药物制剂，以及其在制备预防或治疗缺血性心脑血管疾病、抗血栓形成和改善心脑循环障碍药物中的应用。本公开的化合物具有优异的水溶性、水溶液稳定性和药代动力学特性，还具有显著的抗血小板聚集、抗血栓形成、抗脑缺血和神经保护活性。与(S)-丁基苯酞和(R/S)-2-(1-羟基-n-戊基)苯甲酸钾（PHPB）相比，本公开的化合物具有明显更好的效果，静脉注射对小鼠的急性毒性明显低于丁基苯酞和 PHPB、在 CHO-hERG 细胞中对 hERG 钾通道的抑制率低于(S)-丁基苯酞，并且在细菌反向突变试验（Ames 试验）中呈阴性结果。
• SALTS FORMED BY 2-(1-ACYLOXY-N-PENTYL) BENZOIC ACID AND BASIC AMINO ACID OR AMINOGUANIDINE, AND PREPARATION METHOD AND APPLICATION THEREOF
  申请人：CHINA PHARMACEUTICAL UNIVERSITY

  公开号：US20220024848A1

  公开（公告）日：2022-01-27

  The present disclosure discloses salts formed by 2-(1-acyloxy-n-pentyl)benzoic acid and basic amino acid or aminoguanidine, a preparation method thereof, pharmaceutical preparations containing these salts, and application thereof in preparation of drugs for preventing or treating ischemic cardiovascular and cerebrovascular diseases, resisting thrombosis and improving cardio-cerebral circulation disorders. The compound of the present disclosure has excellent water solubility, aqueous solution stability and pharmacokinetic properties, also has significant anti-platelet aggregation, anti-thrombosis, anti-cerebral ischemia and neuroprotective activity. The compound of the present disclosure has significantly better effects than those of (S)-butylphthalide and potassium (R/S)-2-(1-hydroxy-n-pentyl) benzoate (PHPB), has significantly lower acute toxicity to mice by intravenous injection than that of butylphthalide and PHPB, has a lower inhibition rate of the hERG potassium channel in CHO-hERG cells than that of (S)-butylphthalide, and has a negative result in Bacterial Reverse Mutation Test (Ames test).
• Organocatalytic α-oxybenzoylation of aldehydes
  作者：Matti J.P. Vaismaa、Sze Chak Yau、Nicholas C.O. Tomkinson

  DOI：10.1016/j.tetlet.2009.03.082

  日期：2009.7

  A simple method for the asymmetric alpha-oxybenzoylation of aldehydes is presented. Treatment of a series of aldehydes with benzoyl peroxide in the presence of a MacMillan imidazolidinone leads directly to the alpha-oxybenzoylated product with excellent levels of asymmetric induction. (C) 2009 Elsevier Ltd. All rights reserved.