2,2-dimethyl-4-(3-ethoxy-3-oxo-1-propenyl)-3-oxazolidinecarboxylic acid 1,1-dimethylethyl ester | 131713-27-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2,2-dimethyl-4-(3-ethoxy-3-oxo-1-propenyl)-3-oxazolidinecarboxylic acid 1,1-dimethylethyl ester
• 英文别名: tert-butyl 4-[(E)-3-ethoxy-3-oxoprop-1-enyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 131713-27-4；134525-18-1；144070-31-5；149406-02-0
• 化学式: C₁₅H₂₅NO₅
• 分子量: 299.367
• InChiKey: OFUWDLHCVDWULD-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-4-(3-ethoxy-3-oxo-1-propenyl)-3-oxazolidinecarboxylic acid 1,1-dimethylethyl ester 在 水 、 碳酸氢钠 、 三氟乙酸 作用下， 生成 4-amino-5-hydroxy-2-pentenoic acid ethyl ester
  参考文献：
  名称：

  A new approach to kainoids through tandem Michael reaction methodology: application to the enantioselective synthesis of (+)- and (-)-.alpha.-allokainic acid and to the formal synthesis of (-)-.alpha.-kainic acid

  摘要：

  A convergent, one-pot construction of functionalized pyrrolidine ring systems has been developed. The method is based on a tandem Michael reaction initiated by an intermolecular conjugate addition of a nitrogen nucleophile to an electrophilic olefin followed by trapping of the generated enolate by a built-in alpha,beta-unsaturated acceptor. After model studies verified the feasibility of the process and gave information about its stereochemical outcome, the strategy was successfully applied to kainoid synthesis. The construction of the basic pyrrolidine skeleton of all the members of the family requires coupling of a suitable electrophilic subunit with a common donor-acceptor fragment containing the nitrogen nucleophile. Thus, the enantioselective synthesis of (+)-alpha-allokainic acid (2) and the formal synthesis of its C-4 epimer (-)-alpha-kainic acid (1), have been accomplished using methyl vinyl ketone and 2-nitro-3-methyl-1,3-butadiene, respectively, as electrophilic partners of (S)-4-(benzylamino)-5-hydroxy-2-pentenoic acid ethyl ester (17), easily derived in six steps from D-serine. Although the acetyl group of methyl vinyl ketone is a logical precursor to the isopropenyl moiety of 2, the use of the nitrobutadiene is more appropriate for the synthesis of 1 because of the startling degree of control of the cyclization stereochemistry exerted by the nitro group.

  DOI：

  10.1021/jo00049a040
• 作为产物：
  描述：

  1,1-二甲基-(r,s)-4-甲酰基-2,2-二甲基-3-噁唑啉羧酸乙酯 、 乙氧甲酰基亚甲基三苯基膦 以 苯 为溶剂， 反应 6.0h， 生成 2,2-dimethyl-4-(3-ethoxy-3-oxo-1-propenyl)-3-oxazolidinecarboxylic acid 1,1-dimethylethyl ester
  参考文献：
  名称：

  A new approach to kainoids through tandem Michael reaction methodology: application to the enantioselective synthesis of (+)- and (-)-.alpha.-allokainic acid and to the formal synthesis of (-)-.alpha.-kainic acid

  摘要：

  A convergent, one-pot construction of functionalized pyrrolidine ring systems has been developed. The method is based on a tandem Michael reaction initiated by an intermolecular conjugate addition of a nitrogen nucleophile to an electrophilic olefin followed by trapping of the generated enolate by a built-in alpha,beta-unsaturated acceptor. After model studies verified the feasibility of the process and gave information about its stereochemical outcome, the strategy was successfully applied to kainoid synthesis. The construction of the basic pyrrolidine skeleton of all the members of the family requires coupling of a suitable electrophilic subunit with a common donor-acceptor fragment containing the nitrogen nucleophile. Thus, the enantioselective synthesis of (+)-alpha-allokainic acid (2) and the formal synthesis of its C-4 epimer (-)-alpha-kainic acid (1), have been accomplished using methyl vinyl ketone and 2-nitro-3-methyl-1,3-butadiene, respectively, as electrophilic partners of (S)-4-(benzylamino)-5-hydroxy-2-pentenoic acid ethyl ester (17), easily derived in six steps from D-serine. Although the acetyl group of methyl vinyl ketone is a logical precursor to the isopropenyl moiety of 2, the use of the nitrobutadiene is more appropriate for the synthesis of 1 because of the startling degree of control of the cyclization stereochemistry exerted by the nitro group.

  DOI：

  10.1021/jo00049a040

文献信息

• Sulfonylaminovalerolactams and derivatives thereof as factor Xa inhibitors
  申请人：Han Wei

  公开号：US20050096309A1

  公开（公告）日：2005-05-05

  The present application describes sulfonylaminovalerolactams and derivatives thereof of Formula Ia-If: or pharmaceutically acceptable salt forms thereof, wherein ring G is a mono- or bicyclic carbocycle or heterocycle. Compounds of the present invention are useful as inhibitors of trypsin-like serine proteases, specifically factor Xa.

  本申请描述了Formula Ia-If的磺酰氨基戊内内酰胺及其衍生物，或其药用可接受的盐形式，其中环G为单环或双环碳环或杂环。本发明的化合物可用作胰蛋白酶样丝氨酸蛋白酶抑制剂，特别是因子Xa的抑制剂。
• SULFONYLAMINOVALEROLACTAMS AND DERIVATIVES THEREOF AS FACTOR XA INHIBITORS
  申请人：Han Wei

  公开号：US20070099922A1

  公开（公告）日：2007-05-03

  The present application describes sulfonylaminovalerolactams and derivatives thereof of Formula Ia-If: or pharmaceutically acceptable salt forms thereof, wherein ring G is a mono- or bicyclic carbocycle or heterocycle. Compounds of the present invention are useful as inhibitors of trypsin-like serine proteases, specifically factor Xa.

  本申请描述了式Ia-If的磺酰氨基戊内酰内酰胺及其衍生物或其药学上可接受的盐形式，其中环G是单环或双环碳环或杂环。本发明的化合物可用作胰蛋白酶样丝氨酸蛋白酶的抑制剂，特别是Xa因子的抑制剂。
• EP1667635A4
  申请人：——

  公开号：EP1667635A4

  公开（公告）日：2008-01-23
• ARGINASE INHIBITORS AND METHODS OF USE THEREOF
  申请人：AstraZeneca AB

  公开号：EP4004004A1

  公开（公告）日：2022-06-01
• US7169795B2
  申请人：——

  公开号：US7169795B2

  公开（公告）日：2007-01-30