(4S)-3-<(E)-4'bromo-4',4'-difluoro-2'-butanoyl>-4-benzyl-2-oxazolidinone | 174003-89-5

• 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: (4S)-3-<(E)-4'bromo-4',4'-difluoro-2'-butanoyl>-4-benzyl-2-oxazolidinone
• 英文别名: (4S)-3-[(E)-4'-bromo-4', 4'-difluoro-2'-butenoyl]-4-benzyl-2-oxazolidinone；(4S)-4-benzyl-3-[(E)-4-bromo-4,4-difluorobut-2-enoyl]-1,3-oxazolidin-2-one
• CAS: 174003-89-5
• 化学式: C₁₄H₁₂BrF₂NO₃
• 分子量: 360.155
• InChiKey: ZERKIMQOIKNECM-MLRMMBSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  二苯亚甲基甘氨酸乙酯 、 (4S)-3-<(E)-4'bromo-4',4'-difluoro-2'-butanoyl>-4-benzyl-2-oxazolidinone 在 lithium diisopropyl amide 作用下， 以 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 以16%的产率得到(4S,3'R,4'R)-3-<3'-bromodifluoromethyl-4'-(diphenylmethylideneamino)-4'ethoxycarbonyl>butanoyl-4-benzyl-2-oxazolidinone
  参考文献：
  名称：

  A highly diastereoselective synthesis of trans-3,4-(difluoromethano)glutamic acid

  摘要：

  Reaction of enantiomerically pure N-(4'-bromo-4',4'-difluorocrotonoyl)oxazolidinone 5 with lithium enolate of N-diphenylmethyldeneglycinate 6 in DMF proceeded in highly diastereoselective manner to give trans-disubstituted gem-difluorocyclopropane 7, which was readily converted to the 3,4-(difluoro- methano)glutamic acid 4.

  DOI：

  10.1016/0040-4020(95)00870-e
• 作为产物：
  描述：

  (4S)-4-苄基-3-(2-溴乙酰基)-1,3-恶唑烷-2-酮 以 四氢呋喃 、 乙腈 为溶剂， 反应 53.0h， 生成 (4S)-3-<(E)-4'bromo-4',4'-difluoro-2'-butanoyl>-4-benzyl-2-oxazolidinone
  参考文献：
  名称：

  A highly diastereoselective synthesis of trans-3,4-(difluoromethano)glutamic acid

  摘要：

  Reaction of enantiomerically pure N-(4'-bromo-4',4'-difluorocrotonoyl)oxazolidinone 5 with lithium enolate of N-diphenylmethyldeneglycinate 6 in DMF proceeded in highly diastereoselective manner to give trans-disubstituted gem-difluorocyclopropane 7, which was readily converted to the 3,4-(difluoro- methano)glutamic acid 4.

  DOI：

  10.1016/0040-4020(95)00870-e

文献信息

• CYCLOPROPYLGLYCINE DERIVATIVES AND METABOLIC-REGULATION TYPE L-GLUTAMATE RECEPTOR AGONIST
  申请人：NIPPON CHEMIPHAR CO., LTD.

  公开号：EP0913389A1

  公开（公告）日：1999-05-06

  A cyclopropylglycine derivative having the following formula: [in which each of R1 and R2 independently represents a hydroxyl group or an alkoxy group having 1 to 6 carbon atoms, each of R3 and R4 independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, and each of X1 and X2 independently represents a halogen atom], and an intermediate compound for the synthesis of the cyclopropylglycine derivative are novel compounds. The cyclopropylglycine derivative shows a selectivity higher than that of the known agonists to metabotropic L-glutamate receptors, and therefore is a metabotropic type agonist to L-glutamate which has excellent characteristics.

  具有下式的环丙基甘氨酸衍生物： [其中 R1 和 R2 各自独立地代表羟基或具有 1 至 6 个碳原子的烷氧基，R3 和 R4 各自独立地代表氢原子或具有 1 至 6 个碳原子的烷基，X1 和 X2 各自独立地代表卤素原子]，以及用于合成环丙基甘氨酸衍生物的中间化合物是新型化合物。环丙基甘氨酸衍生物对 L-谷氨酸代谢型受体的选择性高于已知的激动剂，因此是一种具有优良特性的 L-谷氨酸代谢型激动剂。
• US6245919B1
  申请人：——

  公开号：US6245919B1

  公开（公告）日：2001-06-12
• A highly diastereoselective synthesis of trans-3,4-(difluoromethano)glutamic acid
  作者：Akira Shibuya、Masahito Kurishita、Chizuru Ago、Takeo Taguchi

  DOI：10.1016/0040-4020(95)00870-e

  日期：1996.1

  Reaction of enantiomerically pure N-(4'-bromo-4',4'-difluorocrotonoyl)oxazolidinone 5 with lithium enolate of N-diphenylmethyldeneglycinate 6 in DMF proceeded in highly diastereoselective manner to give trans-disubstituted gem-difluorocyclopropane 7, which was readily converted to the 3,4-(difluoro- methano)glutamic acid 4.