(R)-3-Acetoxybuttersaeure | 52020-45-8

• 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: (R)-3-Acetoxybuttersaeure
• 英文别名: (R)-(-)-3-acetoxybutyric acid；(3R)-3-(Acetyloxy)butanoic acid；(3R)-3-acetyloxybutanoic acid
• CAS: 52020-45-8
• 化学式: C₆H₁₀O₄
• 分子量: 146.143
• InChiKey: RVBYGWWJLVDBHM-SCSAIBSYSA-N

物化性质

• 沸点：
  120-130 °C(Press: 0.05 Torr)
• 密度：
  1.159±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-3-Acetoxybuttersaeure 在 氢氧化钾 作用下， 生成 (R)-3-羟基丁酸
  参考文献：
  名称：

  Serck-Hanssen et al., Arkiv foer Kemi, 1953, vol. 5, p. 203,209

  摘要：

  DOI：
• 作为产物：
  描述：

  (+/-)-3-Acetoxy-buttersaeure 在 吗啡 作用下， 生成 (R)-3-Acetoxybuttersaeure
  参考文献：
  名称：

  Serck-Hanssen et al., Arkiv foer Kemi, 1953, vol. 5, p. 203,209

  摘要：

  DOI：

文献信息

• Chirale Synthesebausteine durchKolbe-Elektrolyse enantiomerenreiner ?-Hydroxy-carbons�urederivate. (R)- und (S)-Methyl-sowie (R)-Trifluormethyl-?-butyrolactone und -?-valerolactone
  作者：Dieter Seebach、Philippe Renaud

  DOI：10.1002/hlca.19850680829

  日期：1985.12.18

  Chiral Building Blocks for Syntheses by Kolbe Electrolysis of Enantiomerically Pure β-Hydroxybutyric-Acid Derivatives. (R)- and (S)-Methyl-, and (R)-Trifluoromethyl-γ-butyrolactones, and -δ-valerolactones

  对映体纯的β-羟基丁酸衍生物的Kolbe电解合成手性结构单元。（R）-和（S）-甲基-和（R）-三氟甲基-γ-丁内酯和-δ-戊内酯
• Herstellung enantiomerenreiner Derivate von 3-Amino- und 3-Mercaptobutters�ure durchSN2-Ring�ffnung des ?-Lactons und eines 1,3-Dixoanons aus der 3-Hydroxybutters� ure
  作者：Axel Griesbeck、Dieter Seebach

  DOI：10.1002/hlca.19870700514

  日期：1987.8.12

  Preparation of Enantiomerically Pure Derivatives of 3-Amino- and 3-Mercaptobutanoic Acid by SN2 Ring Opening of the β-Lactone and a 1,3-Dioxanone Derived from 3-Hydroxybutanoic Acid

  通过β-内酯和3-羟基丁酸衍生的1,3-二恶烷酮的S N 2开环制备3-氨基和3-巯基丁酸的对映体纯衍生物
• IMMUNOMODULATORY COMPOUNDS AND TREATMENT OF DISEASES RELATED TO AN OVERPRODUCTION OF INFLAMMATORY CYTOKINES
  申请人：OM PHARMA

  公开号：US20140086960A1

  公开（公告）日：2014-03-27

  Method of using immunomodulatory compounds for treating diseases related to an overproduction of inflammatory cytokines, including diseases selected from asthma, atopic dermatitis, allergic rhinitis, prostatitis, inflammatory bowel disease, diabetes, and rheumatoid arthritis, the compounds being of general formula (I): wherein: m and n, independently from each other, are an integer ranging from 1 to 4, X and Y represent —COOH, —O—P(O)(OH) 2 , —O—SO 2 (OH), —NH 2 , —OH, —CONH(CH 2 ) n1 —NH 2 , —CO—NH—CH(COOH)—(CH 2 ) n1 —COOH, —CO—NH—CH(COOH)—(CH 2 ) n1 —NH 2 , —O—CO—(CH 2 ) n1 —NH 2 , —O—CO—(CH 2 ) n1 —CHOH—CH 2 OH, —O—CO—(CH 2 ) n1 —OH, —O—CO—(CH 2 ) n1 —COOH, —O—CO—(CH 2 ) n1 —CHO, —O—CO—(CH 2 ) n1 —NH—CO—(CH 2 ) n2 —COOH, R 1 and R 2 each designate an acyl group derived from a saturated or unsaturated, straight-or branched-chain carboxylic acid having from 2 to 18 carbon atoms, which is unsubstituted or bears one to three substituents selected among hydroxyl, dihydroxyphosphoryloxy, alkyl of 2 to 18 carbon atoms, alkoxy of 2 to 18 carbon atoms, acyloxy of 2 to 18 carbon atoms in the acyl moiety, amino, acylamino.

  使用免疫调节化合物治疗与炎症细胞因子过度产生相关的疾病的方法，包括哮喘、特应性皮炎、过敏性鼻炎、前列腺炎、炎症性肠病、糖尿病和类风湿性关节炎等疾病，所述化合物的一般式（I）如下：其中：m和n独立地为1至4的整数，X和Y代表—COOH，—O—P（O）（OH）2，—O—SO2（OH），—NH2，—OH，—CONH（CH2）n1—NH2，—CO—NH—CH（COOH）—（CH2）n1—COOH，—CO—NH—CH（COOH）—（CH2）n1—NH2，—O—CO—（CH2）n1—NH2，—O—CO—（CH2）n1—CHOH—CH2OH，—O—CO—（CH2）n1—OH，—O—CO—（CH2）n1—COOH，—O—CO—（CH2）n1—CHO，—O—CO—（CH2）n1—NH—CO—（CH2）n2—COOH，R1和R2各自指代从饱和或不饱和的直链或支链羧酸衍生的酰基，其具有2至18个碳原子，未取代或带有1至3个氢氧基磷酸二酯氢氧基、2至18个碳原子的烷基、2至18个碳原子的烷氧基、酰氧基为酰基部分的2至18个碳原子的酰氧基、氨基、酰胺基中的一种或多种取代基。
• NMDA Receptor Modulators and Uses Thereof
  申请人：Northwestern University

  公开号：US20150315237A1

  公开（公告）日：2015-11-05

  Disclosed are compounds having enhanced potency in the modulation of NMDA receptor activity. Such compounds are contemplated for use in the treatment of diseases and disorders, such as learning, cognitive activities, and analgesia, particularly in alleviating and/or reducing neuropathic pain. Orally available formulations and other pharmaceutically acceptable delivery forms of the compounds, including intravenous formulations, are also disclosed.

  本发明涉及具有增强的NMDA受体活性调节功效的化合物。这些化合物可用于治疗疾病和障碍，如学习、认知活动和镇痛，特别是在缓解和/或减轻神经病理性疼痛方面。本发明还揭示了口服制剂和其他药学上可接受的化合物递送形式，包括静脉注射制剂。
• Synthesis and Structure of Linear and Cyclic Oligomers of 3-Hydroxybutanoic Acid with Specific Sequences of (R)- and (S)-Configurations
  作者：Beat M. Bachmann、Dieter Seebach

  DOI：10.1002/(sici)1522-2675(19981216)81:12<2430::aid-hlca2430>3.0.co;2-w

  日期：1998.12.16

  To study the stereoselectivity of enzymatic cleavage of poly(3-hydroxybutyrates) (PHB) in a well-defined system (purified depolymerase and monodisperse substrate of specific relative configuration), linear and cyclic oligomers of HE (OHBs) containing (R)- and (S)-3-hydroxybutanoate residues were synthesized. The starting material (R)-HB was prepared from natural sPHB, and (S)-HB by enantioselective reduction of 3-oxobutanoate: with yeast or with H-2/Noyori-Taber catalyst (Scheme 2). The HE building blocks were then protected (O-benzyl/tert-butyl ester; Scheme 3) and coupled to give dimers 3, 4 tetramers 5-9, and octamers 10-18; for analytical comparison, a 3mer, 5mer, 6mer, and 7mer (19-22) were also prepared. Two of the tetramers were subjected to macrolactonization conditions (Yamaguchi) to give the cyclic tetramers 23 and 25 and octamers 24 and 26. All new compounds were fully characterized (m.p., [alpha](D), CD, IR, H-1- and C-13-NMR, MS, elemental analysis). Single-crystal X-ray structure analyses were performed with oligolides 24 and 25 ( Figs. 2 and 4), and the structures, as well as the crystal packing, were compared with those of analogs containing only (R)-HB units or consisting of 3-amino- instead of 3-hydroxybutanoic-acid moieties.