(S)-2,2-二甲基-1,3-二氧戊环-4-乙腈 | 131724-43-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (S)-2,2-二甲基-1,3-二氧戊环-4-乙腈
• 英文名称: [(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acetonitrile
• 英文别名: S-3,4-O-isopropylidene-3,4-dihydroxybutyronitrile；(S)-2,2-dimethyl-1,3-dioxolane-4-acetonitrile；2-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]acetonitrile
• CAS: 131724-43-1
• 化学式: C₇H₁₁NO₂
• 分子量: 141.17
• InChiKey: UJLINZVKIKLEHQ-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  42.2
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xn
• 危险类别码：
  R22,R36,R43
• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  (S)-2,2-二甲基-1,3-二氧戊环-4-乙腈 在 三氟乙酸 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以61%的产率得到(3S)-3,4-dihydroxybutyronitrile
  参考文献：
  名称：

  A Novel Agonist of the Type 1 Lysophosphatidic Acid Receptor (LPA₁), UCM-05194, Shows Efficacy in Neuropathic Pain Amelioration

  摘要：

  Neuropathic pain (NP) is a complex chronic pain state with a prevalence of almost 10% in the general population. Pharmacological options for NP are limited and weakly effective, so there is a need to develop more efficacious NP attenuating drugs. Activation of the type 1 lysophosphatidic acid (LPA(1)) receptor is a crucial factor in the initiation of NP. Hence, it is conceivable that a functional antagonism strategy could lead to NP mitigation. Here we describe a new series of LPA(1) agonists among which derivative (S)-17 (UCM-05194) stands out as the most potent and selective LPA(1) receptor agonist described so far (E-max = 118%, EC50 = 0.24 mu M, KD = 19.6 nM; inactive at autotaxin and LPA(2-6) receptors). This compound induces characteristic LPA(1)-mediated cellular effects and prompts the internalization of the receptor leading to its functional inactivation in primary sensory neurons and to an efficacious attenuation of the pain perception in an in vivo model of NP.

  DOI：

  10.1021/acs.jmedchem.9b01287
• 作为产物：
  描述：

  (S)-(+)-1,2-异亚丙基甘油 在 吡啶 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 0.5h， 生成 (S)-2,2-二甲基-1,3-二氧戊环-4-乙腈
  参考文献：
  名称：

  A Novel Agonist of the Type 1 Lysophosphatidic Acid Receptor (LPA₁), UCM-05194, Shows Efficacy in Neuropathic Pain Amelioration

  摘要：

  Neuropathic pain (NP) is a complex chronic pain state with a prevalence of almost 10% in the general population. Pharmacological options for NP are limited and weakly effective, so there is a need to develop more efficacious NP attenuating drugs. Activation of the type 1 lysophosphatidic acid (LPA(1)) receptor is a crucial factor in the initiation of NP. Hence, it is conceivable that a functional antagonism strategy could lead to NP mitigation. Here we describe a new series of LPA(1) agonists among which derivative (S)-17 (UCM-05194) stands out as the most potent and selective LPA(1) receptor agonist described so far (E-max = 118%, EC50 = 0.24 mu M, KD = 19.6 nM; inactive at autotaxin and LPA(2-6) receptors). This compound induces characteristic LPA(1)-mediated cellular effects and prompts the internalization of the receptor leading to its functional inactivation in primary sensory neurons and to an efficacious attenuation of the pain perception in an in vivo model of NP.

  DOI：

  10.1021/acs.jmedchem.9b01287

文献信息

• Process for the preparation of oxazolidinones and method of use thereof
  申请人：Hollingsworth I. Rawle

  公开号：US20070265451A1

  公开（公告）日：2007-11-15

  A process for preparing N-(substituted)-C-(substituted methyl)-oxazolidinones, C-(substituted methyl)-oxazolidinones, and N-(substituted)-C-(substituted methyl)-oxazolidinones, preferably chiral, from optically active C-(protected oxymethyl)-oxazolidinones is described. The process can be used to produce combinatorial libraries of the above substituted oxazolidinones in a two or three step reaction comprising a plurality of reagents differing in numbers of carbons or particular substituted oxazolidinones. A number of substituted oxazolidinones produced using the above process have been discovered to have antimicrobial activity.

  本文介绍了一种从光学活性的C-（保护的氧甲基）-噁唑烷酮制备N-（取代）-C-（取代甲基）-噁唑烷酮、C-（取代甲基）-噁唑烷酮和N-（取代）-C-（取代甲基）-噁唑烷酮的方法，其中优选手性化合物。该方法可用于在包含多种碳数或特定取代噁唑烷酮的多种试剂的两步或三步反应中产生上述取代噁唑烷酮的组合库。使用上述方法生产的许多取代噁唑烷酮已被发现具有抗微生物活性。
• PROCESS FOR THE PREPARATION OF OXAZOLIDINONES AND METHOD OF USE THEREOF
  申请人：Hollingsworth Rawle I.

  公开号：US20080146458A1

  公开（公告）日：2008-06-19

  Substituted oxazolidinone of the formula: wherein R 2 is alkyl selected from the group consisting of methyl, ethyl, and isopropyl moieties, are described. The compounds are antibacterial.

  描述了以下化学式的氧杂环丙酮类替代物：其中R2是选择自甲基，乙基和异丙基基团的烷基。这些化合物具有抗菌作用。
• Process for the production of 3,5,6-trihydroxyhexanoic acid derivative
  申请人：Kanegafuchi Chemical Industry Co., Ltd.

  公开号：EP0374922A2

  公开（公告）日：1990-06-27

  A compound of a 3,5,6-trihydroxyhexanoic acid derivative of the formula: wherein P¹ and P² are independently hydrogen atoms or hydroxy-protecting groups, or together form a ring, and R is an alkyl group is effectively prepared by a process comprising steps of: reacting a butyronitrile derivative of the formula: wherein P¹ and P² are the same as defined above with an α-haloacetate of the formula: X-CH₂-COOR      (III) wherein X is a halogen atom, and R is the same as defined above in the presence of a metallic catalyst selected from the group consisting zinc and zinc-copper to form a keto acid derivative of the formula: wherein P¹, P² and R are the same as defined above, and then reducing the obtained keto-acid derivative of the formula (IV).

  一种式 3，5，6-三羟基己酸衍生物化合物： 其中 P¹ 和 P² 独立地为氢原子或羟基保护基团，或共同形成一个环，且 R 为烷基，可通过包括以下步骤的工艺有效地制备： 使以下式子的丁腈衍生物反应 式中 P¹ 和 P² 与上式定义相同的α-卤代乙酸酯反应： x-ch₂-coor (iii) 其中 X 为卤素原子，R 与上式所定义的相同，在选自锌和锌-铜组成的金属催化剂存在下，生成式如下的酮酸衍生物： 其中 P¹、P² 和 R 与上述定义相同，以及 然后还原得到的式 (IV) 酮酸衍生物。
• US4983759A
  申请人：——

  公开号：US4983759A

  公开（公告）日：1991-01-08
• US7390825B1
  申请人：——

  公开号：US7390825B1

  公开（公告）日：2008-06-24