3-(2-oxooxazolidin-3-yl)propionic acid methyl ester | 86241-71-6

• 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: 3-(2-oxooxazolidin-3-yl)propionic acid methyl ester
• 英文别名: methyl 3-(2-oxooxazolidin-3-yl)propanoate；3-(2-oxo-oxazolidin-3-yl)-propionic acid methyl ester；3-(2-Oxo-oxazolidin-3-yl)-propionsaeure-methylester；Methyl 3-(2-oxo-1,3-oxazolidin-3-yl)propanoate
• CAS: 86241-71-6
• 化学式: C₇H₁₁NO₄
• 分子量: 173.169
• InChiKey: VMBQLTXUYUJJCF-UHFFFAOYSA-N

物化性质

• 沸点：
  147-155 °C(Press: 0.05 Torr)
• 密度：
  1.224±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-唑烷酮 、 丙烯酸甲酯（MA） 在 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine supported on polystyrene 作用下， 反应 72.0h， 以99%的产率得到3-(2-oxooxazolidin-3-yl)propionic acid methyl ester
  参考文献：
  名称：

  E因子最小化方案，用于各种苯乙烯基聚苯乙烯-BEMP催化的共轭物向α，β-不饱和羰基化合物的共轭加成

  摘要：

  添加碳，硫和硫的有效方案 氮-亲核体为α，β-不饱和 羰基化合物已经报道了由PS-BEMP催化。通过溶剂无溶剂条件（SolFC）对于提高所有过程的效率至关重要，而通过使用有机反应介质，则可获得较差的结果。使用等摩尔量的试剂进行加成反应，并通过简单的方法分离出产物过滤 用最少的有机物 溶剂。这种方法可以最大程度地减少E因子（反应浪费的量度）。通过定义在SolFC下运行的更大规模的连续流协议，可以实现进一步的废物最小化（与批处理协议相比为95.7％）。

  DOI：

  10.1039/c1gc16088e

文献信息

• Synthesis of Oxazolidin-2-ones by Oxidative Coupling of Isonitriles, Phenyl Vinyl Selenone, and Water
  作者：Thomas Buyck、Delphine Pasche、Qian Wang、Jieping Zhu

  DOI：10.1002/chem.201505050

  日期：2016.2.12

  unprecedented heteroannulation process created four chemical bonds in a single operation with the isocyano group acting formally as a polarized double bond and phenyl vinyl selenone as a latent 1,3‐dipole. The phenylselenonyl group played a triple role as an electron‐withdrawing group to activate the 1,4‐addition, a leaving group, and a latent oxidant in this transformation.

  在催化量的Cs 2 CO 3存在下，烷基异氰化物，苯基乙烯基硒酮和水的反应得到了恶唑烷-2-酮，收率很高。这种空前的异环化过程在一次操作中产生了四个化学键，异氰基在形式上起极化双键作用，苯基乙烯基硒酮起潜在的1,3-偶极作用。苯基硒壬基在该转化过程中作为吸电子基团发挥了三重作用，以激活1,4加成，一个离去基团和一个潜在的氧化剂。
• Highly efficient KF/Al2O3-catalyzed versatile hetero-Michael addition of nitrogen, oxygen, and sulfur nucleophiles to α,β-ethylenic compounds
  作者：Lei Yang、Li-Wen Xu、Chun-Gu Xia

  DOI：10.1016/j.tetlet.2005.03.112

  日期：2005.5

  of KF/Al2O3-catalyzed versatile hetero-Michael addition reaction of nitrogen, oxygen, and sulfur nucleophiles was developed for facile preparation of organic compounds of widely different structures. In contrast with the existing methods using many acidic catalysts, this method is very general, simple, high-yielding, environmentally friendly, and oxygen and moisture tolerant.

  开发了KF / Al 2 O 3催化的氮，氧和硫亲核试剂的多功能杂-迈克尔加成反应的第一个实例，可轻松制备结构迥异的有机化合物。与使用许多酸性催化剂的现有方法相比，该方法非常通用，简单，高产率，环境友好并且耐氧气和湿气。
• Adducts of heterocyclic amides
  申请人：ROHM &

  公开号：US02852512A1

  公开（公告）日：1958-09-16

  Polyvinyl chloride is plasticized by means of a heterocyclic amide or thioamide containing two nitrogen atoms in the ring, both of which are substituted by different groups, the compounds being adducts of heterocyclic amides or thioamides with a : b -ethylenically unsaturated compounds, all of specified types (see Group IV(b)). The compounds also have fungicidal properties. 1-(2- vinoxyethyl)- 3- (2- cyanoethyl)- 2- imidaxolidinone, a specified adduct, may be homopolymerized with the aid of Friedel-Crafts catalysts and co-polymerized with acrylate esters, maleic anhydride, alkyl fumarates and vinyl compounds using free-radical initiators. Another adduct, 1- (2-methacryloyl oxyethyl)- 3-(2-methoxycarbonylpropyl)-2-imidazolidinone may be homopolymerized using free-radical type catalysts and may be copolymerized with monomers such as acrylates and acrylonitrile.ALSO:The invention comprises heterocyclic amides and thioamides containing two nitrogen atoms in the ring both of which are substituted by different groups, the compounds being adducts of heterocyclic compounds of the general formula <;FORM:0875135/IV (b)/1>; and unsaturated compounds of the formula <;FORM:0875135/IV (b)/2>; wherein L is a divalent chain of two or three carbon atoms and one nitrogen atom which, considered in a counter-clockwise direction, is separated from the other nitrogen atom in the heterocyclic ring by at least two carbon atoms, the remaining valencies of the said two or three carbon atoms in the L chain being satisfied by hydrogen atoms or alkyl groups which, if desired, may be joined together to form a carbocyclic system embracing the two or three carbon atoms of the L chain and whose total carbon content is no greater than 18, with the proviso that when the N atom in the L chain is vicinal to the carbon atom shown in the formula and the L chain contains 3 carbon atoms, the middle carbon atom may bear a hydroxy substituent; the available valency of the N atom in the L chain is satisfied by an alkyl, cycloalkyl or alkyl cycloalkyl group containing up to 18 carbon atoms, an aryl, alkaryl, aralkyl or alkaralkyl group containing 6-18 carbon atoms, a C2-C8 hydroxy- or amino-alkyl group in which the hydroxy- or amino-group is no closer than the b -position to the N atom in the L chain, a C2-C18 alkenyl group, an alkoxyalkyl group containing up to 19 carbon atoms in which the alkoxy portion contains up to 16 and the alkyl portion at least 2 carbon atoms, an alkenoxyalkyl group containing up to 19 carbon atoms in which the alkenoxy portion contains up to 17 and the alkyl portion at least 2 carbon atoms, or a cyano group or cyano alkyl group having up to 8 carbons in the alkyl group; Y is oxygen or sulphur; Q is hydrogen or a C1-C8 alkyl group; and T is a cyano group, the group -CONZ2 in which Z is hydrogen or a C1-C8 alkyl group, or the group -COOR in which R is a C1-C14 alkyl group, a C2-C14 alkoxyalkyl group, an aralkyl or alkaralkyl group containing 7-14 carbons or a cycloalkyl or alkyl cycloalkyl group containing up to 14 carbon atoms. The adducts are prepared by an addition reaction between the two components at about 0 DEG -200 DEG C. in the presence of a strongly alkaline catalyst and, if desired, an inert volatile solvent. When the substituent on the N atom of the L chain is a cyanalkyl group, the unsaturated reactant is so selected that the substituent introduced on to the other N atom is different. When the N atom of the L chain contains a hydroxyalkyl substituent and the unsaturated reactant contains an ester group, esterification of this hydroxy group may occur, in addition to adduct formation. Those adducts containing an ester group wherein R is derived from a higher alcohol may be obtained advantageously by first forming the corresponding adduct wherein R is a lower alkyl group and then subjecting this adduct to transesterification to obtain the higher molecular weight ester. The adducts may be used as synthetic lubricants, fungicides or plasticizers and some may be polymerized (see Group IV(a)). Examples d scribe the preparations of (1) 1-(2-vinoxyethyl)-3-(2-cyanoethyl)-2-imidazolidinone from acrylonitrile and 1-(2-vinoxyethyl)-2-imidazolidinone; (2) 1 - (2-methacryloyloxyethyl)-3-(2-methoxy carbonyl propyl) - 2 - imidazolidinone from methyl methylacrylate and 1-(2-hydroxyethyl)-2-imidazolidinone; (3) 1-(2-methoxy carbonyl ethyl) - 3:3:4:5 - tetramethyl - 2 - piperazinone from methyl acrylate and tetramethyl-2-piperazinone; (4) 1-(3-amino propyl)-3-(2-methoxy carbonyl ethyl)-2-piperimidinone from methyl acrylate and 1-(3-amino propyl)-2-piperimidinone. Numerous other adducts and adduct-forming reagents including imidazolidinthiones, piperazinthiones and piperimidinthiones are listed.ALSO:Fungicidal compositions comprise an inert carrier containing up to 1% of a heterocyclic amide or thioamide containing two nitrogen atoms in the ring both of which are substituted by different groups, the compounds being adducts of heterocyclic amides or thio amides with a : b -ethylenically unsaturated compounds, all of specified types (see Group IV (b)). Typical of many named adducts are 1-(2-vinoxyethyl)-3 - (2 - cyanoethyl) - 2 - imidazolidinone 1 - (2-methacryloyloxyethyl) - 3 - (2 - methoxy carbonyl propyl) - 2 - imidazolidinone, 1 - (2 - methoxy carbonyl ethyl) - 3 : 3 : 4 : 5 - tetramethyl-2 - piperazinone and 1 - (3 - amino propyl) - 3-2 - methoxycarbonyl ethyl) - 2 - piperimidinone.

  聚氯乙烯通过含有两个氮原子的杂环酰胺或硫酰胺进行增塑，环中的两个氮原子都被不同的基团取代，这些化合物是杂环酰胺或硫酰胺与a：b-乙烯不饱和化合物的加合物，均为特定类型（请参见IV(b)组）。这些化合物还具有杀真菌作用。1-(2-乙烯氧基乙基)-3-(2-氰基乙基)-2-咪唑啉酮，一种特定的加合物，可在弗里德尔-克拉夫特催化剂的帮助下进行均聚，并可与丙烯酸酯、马来酸酐、烯丙基丙烯酸酯和乙烯化合物共聚，使用自由基引发剂。另一种加合物，1-(2-甲基丙烯酰氧基乙基)-3-(2-甲氧羰基丙基)-2-咪唑啉酮，可使用自由基型催化剂进行均聚，并可与丙烯酸酯和丙烯腈等单体共聚。此外，该发明涉及含有两个氮原子的杂环酰胺和硫酰胺，环中的两个氮原子都被不同的基团取代，这些化合物是杂环化合物的加合物，其一般公式为<;FORM:0875135/IV (b)/1>;和不饱和化合物的公式为<;FORM:0875135/IV (b)/2>;其中L是由两个或三个碳原子和一个氮原子组成的二价链，按逆时针方向考虑，与杂环环中的另一个氮原子至少相隔两个碳原子，L链中的这两个或三个碳原子的剩余价由氢原子或烷基取代，如有需要，可以结合形成包含L链上的两个或三个碳原子的碳环系统，其总碳含量不超过18，条件是当L链中的N原子与公式中显示的碳原子相邻且L链含有3个碳原子时，中间碳原子可能带有一个羟基取代基；L链中的N原子的可用价由一个含有多达18个碳原子的烷基、环烷基或烷基环烷基基团、含有6-18个碳原子的芳基、烷芳基、芳基烷基或烷基芳基基团、一个C2-C8羟基或氨基烷基基团，其中羟基或氨基团至少与L链中的N原子的b-位置不相邻，一个C2-C18烯基基团、一个含有多达19个碳原子的烷氧基烷基基团，其中烷氧部分含有多达16个碳原子，烷基部分至少含有2个碳原子，一个含有多达19个碳原子的烯氧基烷基基团，其中烯氧部分含有多达17个碳原子，烷基部分至少含有2个碳原子，或一个含有多达8个碳原子的氰基或氰基烷基基团；Y是氧或硫；Q是氢或一个C1-C8烷基基团；T是一个氰基团，-CONZ2中的Z是氢或一个C1-C8烷基基团，或-COOR中的R是一个C1-C14烷基基团、一个含有7-14个碳原子的C2-C14烷氧基烷基基团、一个芳基烷基或烷基芳基基团，或一个含有多达14个碳原子的环烷基或烷基环烷基基团。这些加合物通过在强碱性催化剂的存在下，在大约0°C至200°C的条件下进行两种组分之间的加成反应制备，并且如有需要，还可以在惰性挥发性溶剂的存在下进行。当L链上的N原子的取代基是氰基烷基基团时，所选的不饱和反应物应使引入到另一个N原子上的取代基不同。当L链的N原子含有羟基烷基取代基且不饱和反应物含有酯基时，除了加合物形成外，还可能发生这个羟基的酯化。含有酯基的那些加合物，其中R是由较高醇类衍生的，可以通过首先形成R为较低烷基基团的相应加合物，然后将此加合物经过酯交换反应获得较高分子量的酯。这些加合物可用作合成润滑剂、杀真菌剂或增塑剂，其中一些可以聚合（见IV(a)组）。示例描述了以下制备过程：（1）从丙烯腈和1-(2-乙烯氧基乙基)-2-咪唑啉酮制备1-(2-乙烯氧基乙基)-3-(2-氰基乙基)-2-咪唑啉酮；（2）从甲基丙烯酸甲酯和1-(2-羟乙基)-2-咪唑啉酮制备1-(2-甲基丙烯酰氧基乙基)-3-(2-甲氧羰基丙基)-2-咪唑啉酮；（3）从丙烯酸甲酯和四甲基-2-哌嗪酮制备1-(2-甲氧羰基乙基)-3:3:4:5-四甲基-2-哌嗪酮；（4）从丙烯酸甲酯和1-(3-氨基丙基)-2-哌嗪酮制备1-(3-氨基丙基)-3-(2-甲氧羰基乙基)-2-哌嗪啉酮。还列出了许多其他加合物和加合物形成试剂，包括咪唑啉硫酮、哌嗪硫酮和哌嗪啉硫酮。此外，杀真菌组合物包括含有高达1%的惰性载体的杂环酰胺或硫酰胺，环中的两个氮原子都被不同的基团取代，这些化合物是杂环酰胺或硫酰胺与a：b-乙烯不饱和化合物的加合物，均为特定类型（请参见IV(b)组）。许多命名的加合物包括1-(2-乙烯氧基乙基)-3-(2-氰基乙基)-2-咪唑啉酮、1-(2-甲基丙烯酰氧基乙基)-3-(2-甲氧羰基丙基)-2-咪唑啉酮、1-(2-甲氧羰基乙基)-3:3:4:5-四甲基-2-哌嗪酮和1-(3-氨基丙基)-3-(2-甲氧羰基乙基)-2-哌嗪啉酮。
• Boronic acid derivatives
  申请人：MERCK PATENT GMBH

  公开号：US10640520B2

  公开（公告）日：2020-05-05

  Compounds of formula (I) are inhibitors of LMP7 and can be employed, inter alia, for the treatment of an autoimmune disorder or hematological malignancies.

  式（I）化合物是 LMP7 的抑制剂，可用于治疗自身免疫性疾病或血液恶性肿瘤等。
• Organocatalyzed cycloaddition of carbon dioxide to aziridines
  作者：Yichen Wu、Guosheng Liu

  DOI：10.1016/j.tetlet.2011.09.092

  日期：2011.11

  An efficient and simple process for the fixation of carbon dioxide (CO2) to aziridine for the synthesis of 2-oxazolidinone by using DBN as catalyst, Lil as an additive under atmospheric pressure was developed. This chemical fixation of CO2 could also be carried out at room temperature with prolonged reaction time. (C) 2011 Elsevier Ltd. All rights reserved.