5-(羟基甲基)-3-(2-甲基-2-丙基)-1,3-恶唑烷-2-酮 | 85665-60-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 中文名称: 5-(羟基甲基)-3-(2-甲基-2-丙基)-1,3-恶唑烷-2-酮
• 英文名称: (R,S)-5-(hydroxymethyl)-3-tert-butyloxazolidin-2-one
• 英文别名: (R,S)-5-hydroxymethyl-3-tert-butyl-oxazolidin-2-one；3-tert-butyl-5-(hydroxymethyl)-1,3-oxazolidin-2-one；3-(tert-butyl)-5-(hydroxymethyl)oxazolidin-2-one；3-tert-butyl-5-(hydroxymethyl)oxazolidin-2-one；3-tert-butyl-5-hydroxymethyloxazolidin-2-one；3-t-butyl-5-hydroxymethyl-oxazolidin-2-one；3-(1,1-Dimethylethyl)-5-(hydroxymethyl)oxazolidin-2-one
• CAS: 85665-60-7
• 化学式: C₈H₁₅NO₃
• 分子量: 173.212
• InChiKey: SSMIUHOOMMVZNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  5-(羟基甲基)-3-(2-甲基-2-丙基)-1,3-恶唑烷-2-酮 在 sodium hydroxide 、 potassium tert-butylate 作用下， 以 甲醇 、 叔丁醇 为溶剂， 反应 20.0h， 生成 噻吗洛尔
  参考文献：
  名称：

  Enantioselective synthesis of (S)-timolol via kinetic resolution of terminal epoxides and dihydroxylation of allylamines

  摘要：

  An efficient enantioselective synthesis of (S)-timolol has been described using chiral Co-salen-catalyzed kinetic resolution of less expensive (+/-)-epichlorohydrin with 3-hydroxy-4-(N-morpholino)-1,2,5-thiadiazole in good overall yield (55%) and excellent enantioselectivity (98%). Synthesis of (S)-timolol has also been achieved using hydrolytic kinetic resolution as well as asymmetric dihydroxylation routes in 90% ee and 56% ee, respectively. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.01.057
• 作为产物：
  描述：

  (3-叔丁基-2-氧代-1,3-恶唑烷-5-基)乙酸甲酯 生成 5-(羟基甲基)-3-(2-甲基-2-丙基)-1,3-恶唑烷-2-酮
  参考文献：
  名称：

  XAMAGUTI, SIGEHKI;YAMAMURA, XIROSI;XASEHGAVA, DZYUNDZO;KAVARADA, XADZIMEH+

  摘要：

  DOI：

文献信息

• Synthesis of Five-membered Heterocycles by Reactions of<i>N</i>-Substituted-2-aminomethyloxiranes with Heterocumulenes
  作者：Michinori Karikomi、Tohru Yamazaki、Takashi Toda

  DOI：10.1246/cl.1993.1965

  日期：1993.11

  Various five-membered heterocyclic compounds were synthesized by the reactions of N-substituted-2-aminomethyloxiranes with several different heterocumulenes in good yields.

  通过N-取代-2-氨基甲基环氧乙烷与几种不同的杂枯草烯以良好的产率反应合成了各种五元杂环化合物。
• Prodrugs of a 3-(pyrrol-2-ylmethylidene)-2-indolinone derivatives
  申请人：Sugen. Inc.

  公开号：US20030100555A1

  公开（公告）日：2003-05-29

  The present invention relates to pyrrole substituted 2-indolinone compounds and their pharmaceutically acceptable salts which modulate the activity of protein kinases and therefore are expected to be useful in the prevention and treatment of protein kinase related cellular disorders such as cancer.

  本发明涉及吡咯替代的2-吲哚酮化合物及其药学上可接受的盐，这些化合物调节蛋白激酶的活性，因此预计在预防和治疗蛋白激酶相关的细胞疾病，如癌症方面具有用处。
• Substrate-Controlled Product Divergence: Conversion of CO₂ into Heterocyclic Products
  作者：Jeroen Rintjema、Roel Epping、Giulia Fiorani、Eddy Martín、Eduardo C. Escudero-Adán、Arjan W. Kleij

  DOI：10.1002/anie.201511521

  日期：2016.3.14

  Substituted epoxy alcohols and amines allow substrate‐controlled conversion of CO2 into a wide range of heterocyclic structures through different mechanistic manifolds. This new approach results in an unusual scope of CO2‐derived products by initial activation of CO2 through either the amine or alcohol unit, thus providing nucleophiles for intramolecular epoxy ring opening under mild reaction conditions

  取代的环氧醇和胺可通过不同的机械歧管，将底物控制的CO 2转化为多种杂环结构。这种新方法通过胺或醇单元对CO 2的初始活化，导致了源自CO 2衍生产品的异常范围，从而在温和的反应条件下为分子内环氧开环提供了亲核试剂。对照实验通过遵循S N i途径的亲核试剂开环步骤和5-exo-tet环化作用，支持了胺/醇片段在该过程中的关键作用，从而形成了杂环骨架。
• Bioisosteric Replacement and Related Analogs in the Design, Synthesis and Evaluation of Ligands for Muscarinic Acetylcholine Receptors
  作者：Richie Bhandare、Daniel Canney

  DOI：10.2174/15734064113096660043

  日期：2014.4

  Previous structure-activity relationship studies involving a series of lactone-based muscarinic ligands identified a lead compound containing a diphenylmethylpiperazine moiety (4; IC50 = 340 nM). The purpose of the present work is to investigate 1,3-benzodioxoles, 4,4-diethyl substituted tetrahydrofurans, 5-substituted oxazolidinones and chromones as bioisosteric replacements for the lactone ring in a novel series of muscarinic ligands. The approach provided compounds with improved % inhibition values and identified a non-selective muscarinic ligand with an IC50 value of 280 nM. The structure-activity relationship for this new series will be discussed. Selected compounds were evaluated in preliminary assays for subtype selectivity and were found to be non-selective.

  之前关于一系列基于内酯的毒蕈碱配体的结构-活性关系研究中，确定了一种含有二苯甲基哌嗪基团的领先化合物（4；IC50 = 340 nM）。本研究的目的是探讨1,3-苯并二氧杂环、4,4-二乙基取代的四氢呋喃、5-取代的噁唑烷酮和色烯作为新系列毒蕈碱配体中内酯环的生物等效替代物。该方法提供了具有改善的抑制率值的化合物，并识别出一种非选择性的毒蕈碱配体，其IC50值为280 nM。将讨论这一新系列的结构-活性关系。选定的化合物在初步实验中进行亚型选择性评估，结果发现它们是非选择性的。
• Switchable synthesis of cyclic carbamates by carbon dioxide fixation at atmospheric pressure
  作者：Yasunori Toda、Minoru Shishido、Tatsuya Aoki、Kimiya Sukegawa、Hiroyuki Suga

  DOI：10.1039/d1cc02493k

  日期：——

  base-promoted switchable synthesis of five- and six-membered cyclic carbamates using atmospheric pressure carbon dioxide as the C1 source was developed. The chemoselectivity of products was simply controlled by changing bases and solvents. The reaction proceeds effectively under mild conditions, affording valuable cyclic carbamates. Experimental results and DFT studies revealed the reaction mechanism.

  开发了使用大气压二氧化碳作为 C1 源的五元和六元环状氨基甲酸酯的碱基促进可切换合成。产品的化学选择性可以通过改变碱和溶剂来简单地控制。该反应在温和条件下有效进行，得到有价值的环状氨基甲酸酯。实验结果和 DFT 研究揭示了反应机理。