4-isopropyl-5,5-dimethyl-2-oxazolidinone | 285994-19-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: 4-isopropyl-5,5-dimethyl-2-oxazolidinone
• 英文别名: (S)-3-(prop-2'-enoyl)-4-iso-propyl-5,5-dimethyloxazolidin-2-one；(S)-5,5-dimethyl-4-iso-propyl-3-acryloyl-oxazolidin-2-one；(S)-3-acryloyl-4-isopropyl-5,5-dimethyloxazolidin-2-one；(4S)-5,5-dimethyl-4-propan-2-yl-3-prop-2-enoyl-1,3-oxazolidin-2-one
• CAS: 285994-19-6
• 化学式: C₁₁H₁₇NO₃
• 分子量: 211.261
• InChiKey: WCONGMNXBDXEGH-VIFPVBQESA-N

物化性质

• 熔点：
  56-57 °C
• 沸点：
  253.7±23.0 °C(Predicted)
• 密度：
  1.052±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-isopropyl-5,5-dimethyl-2-oxazolidinone 在 正丁基锂 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 18.5h， 生成 (2'S,4S)-5,5-dimethyl-4-iso-propyl-3-[3'-(N,N-dibenzylamino)-2'-ethyl-propanoyl]oxazolidin-2-one
  参考文献：
  名称：

  [EN] MODULATORS OF G-PROTEIN COUPLED RECEPTORS
  [FR] MODULATEURS DE RÉCEPTEURS COUPLÉS À LA PROTÉINE G

  摘要：

  This disclosure features chemical entities (e.g., a compound or a pharmaceutically acceptable salt) that modulate (e.g., agonize or partially agonize or antagonize) glucagonlike peptide-1 receptor ("GLP-1R") and/or the gastric inhibitory polypeptide receptor ("GIPR"). The chemical entities are useful, e.g., for treating a disease, disorder, or condition in which modulation (e.g., agonism, partial agonism or antagonism) of GLP-1R and/or GIPR activities is beneficial for the treatment or prevention of the underlying pathology and/or symptoms and/or progression of the disease, disorder, or condition. In some embodiments, modulation results in enhancement of (e.g., increases) existing levels (e.g., normal or below normal levels) of GLP-1R and/or GIPR activity (e.g., signaling). In some embodiments, the chemical entities described herein further modulate (e.g., attenuate, uncouple) β -arrestin signaling relative to what is observed with the native ligand. This disclosure also features compositions as well as other methods of using and making the said chemical entities.

  公开号：

  WO2022241287A2
• 作为产物：
  描述：

  丙烯酸酐 、 (4S)-4-异丙基-5,5-二甲基-1,3-恶唑烷-2-酮 在 三乙胺 、 lithium chloride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以1.06 g的产率得到4-isopropyl-5,5-dimethyl-2-oxazolidinone
  参考文献：
  名称：

  SuperQuat 5,5-dimethyl-4-iso-propyloxazolidin-2-one as a mimic of Evans 4-tert-butyloxazolidin-2-one

  摘要：

  在手性噁唑啉酮的5位引入一个双甲基基团会使得邻近的C(4)立体导向基团倾向于特定构象，即双甲基-4-异丙基的组合能模拟一个C(4)叔丁基基团，从而实现更高的立体控制水平，优于简单的4-异丙基噁唑啉酮。这一原理的普遍性在立体选择性烯醇化物烷基化、动力学拆分、狄尔斯-阿尔德环加成和钯催化的不对称缩醛化反应中得到了应用验证。

  DOI：

  10.1039/b605244d

文献信息

• SuperQuat 5,5-dimethyl-4-iso-propyloxazolidin-2-one as a mimic of Evans 4-tert-butyloxazolidin-2-one
  作者：Steven D. Bull、Stephen G. Davies、A. Christopher Garner、Dennis Kruchinin、Min-Suk Key、Paul M. Roberts、Edward D. Savory、Andrew D. Smith、James E. Thomson

  DOI：10.1039/b605244d

  日期：——

  The incorporation of a gem-dimethyl group at the 5-position of a chiral oxazolidinone biases the conformation of the adjacent C(4)-stereodirecting group such that the gem-dimethyl-4-iso-propyl combination mimics a C(4)-tert-butyl group, providing higher levels of stereocontrol than a simple 4-iso-propyloxazolidinone. The generality of this principle is demonstrated with applications in stereoselective enolate alkylations, kinetic resolutions, Diels–Alder cycloadditions and Pd-catalysed asymmetric acetalisation reactions.

  在手性噁唑啉酮的5位引入一个双甲基基团会使得邻近的C(4)立体导向基团倾向于特定构象，即双甲基-4-异丙基的组合能模拟一个C(4)叔丁基基团，从而实现更高的立体控制水平，优于简单的4-异丙基噁唑啉酮。这一原理的普遍性在立体选择性烯醇化物烷基化、动力学拆分、狄尔斯-阿尔德环加成和钯催化的不对称缩醛化反应中得到了应用验证。
• Metal ion-mediated diastereoface-selective 1,3-dipolar cycloaddition of nitrile oxides with dipolarophiles bearing an oxazolidinone chiral auxiliary
  作者：Hidetoshi Yamamoto、Sadaka Watanabe、Keiko Kadotani、Masayuki Hasegawa、Michihiko Noguchi、Shuji Kanemasa

  DOI：10.1016/s0040-4039(00)00369-5

  日期：2000.4

  cycloaddition reactions of nitrile oxides to chiral 3-acryloyl-2-oxazolidinones lead to highly diastereoselective formation of 2-isoxazolines. The magnesium ion serves to fix the α,β-unsaturated moiety through chelation to effect chiral shielding. These asymmetric reactions provide the first successful examples of Lewis acid-mediated stereocontrol of nitrile oxide cycloaddition reactions to electron-deficient

  镁离子介导的腈氧化物与手性3-丙烯酰基-2-恶唑烷酮的环加成反应导致2-异恶唑啉的高度非对映选择性形成。镁离子通过螯合固定α，β-不饱和部分，以实现手性屏蔽。这些不对称反应提供了路易斯酸介导的氮氧化物环加成反应对电子缺陷型双亲亲子的立体控制的第一个成功实例。
• Asymmetric synthesis of β2-amino acids: 2-substituted-3-aminopropanoic acids from N-acryloyl SuperQuat derivatives
  作者：James E. Beddow、Stephen G. Davies、Kenneth B. Ling、Paul M. Roberts、Angela J. Russell、Andrew D. Smith、James E. Thomson

  DOI：10.1039/b707689d

  日期：——

  Conjugate addition of lithium dibenzylamide to (S)-N(3)-acryloyl-4-isopropyl-5,5-dimethyloxazolidin-2-one (derived from l-valine) and alkylation of the resultant lithium beta-amino enolate provides, after deprotection, a range of (S)-2-alkyl-3-aminopropanoic acids in good yield and high ee. Alternatively, via a complementary pathway, conjugate addition of a range of secondary lithium amides to (S)

  在（S）-N（3）-丙烯酰基-4-异丙基-5,5-二甲基恶唑烷丁二酮（衍生自l-缬氨酸）上共轭添加二苄基氨基锂，然后将所得的β-氨基烯醇锂烷基化脱保护时，一系列（S）-2-烷基-3-氨基丙酸的收率和ee高。或者，通过互补途径，将一系列仲氨基酰胺共轭添加到（S）-N（3）-（2'-烷基丙烯酰基）-4-异丙基-5,5-二甲基恶唑烷-2-酮中，用2-吡啶酮以及随后的脱保护作用以高收率和高ee提供了一系列（R）-2-烷基-和（R）-2-芳基-3-氨基丙酸。另外，硼介导的β-氨基N-酰基恶唑烷酮的醛醇缩合反应是用于合成一系列β-氨基-β'-羟基N-酰基恶唑烷酮的高度非对映选择性的方法。
• [EN] MODULATORS OF G-PROTEIN COUPLED RECEPTORS<br/>[FR] MODULATEURS DE RÉCEPTEURS COUPLÉS À LA PROTÉINE G
  申请人：[en]CARMOT THERAPEUTICS, INC.

  公开号：WO2022241287A2

  公开（公告）日：2022-11-17

  This disclosure features chemical entities (e.g., a compound or a pharmaceutically acceptable salt) that modulate (e.g., agonize or partially agonize or antagonize) glucagonlike peptide-1 receptor ("GLP-1R") and/or the gastric inhibitory polypeptide receptor ("GIPR"). The chemical entities are useful, e.g., for treating a disease, disorder, or condition in which modulation (e.g., agonism, partial agonism or antagonism) of GLP-1R and/or GIPR activities is beneficial for the treatment or prevention of the underlying pathology and/or symptoms and/or progression of the disease, disorder, or condition. In some embodiments, modulation results in enhancement of (e.g., increases) existing levels (e.g., normal or below normal levels) of GLP-1R and/or GIPR activity (e.g., signaling). In some embodiments, the chemical entities described herein further modulate (e.g., attenuate, uncouple) β -arrestin signaling relative to what is observed with the native ligand. This disclosure also features compositions as well as other methods of using and making the said chemical entities.