4(S)-amino-4-(methoxymethylcarbamoyl)butyric acid tert-butyl ester | 279675-06-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4(S)-amino-4-(methoxymethylcarbamoyl)butyric acid tert-butyl ester
• CAS: 279675-06-8
• 化学式: C₁₁H₂₂N₂O₄
• 分子量: 246.307
• InChiKey: XFVRMQZYUJWBSF-QMMMGPOBSA-N

物化性质

• 沸点：
  324.2±52.0 °C(predicted)
• 密度：
  1.078±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.46
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  81.86
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4(S)-amino-4-(methoxymethylcarbamoyl)butyric acid tert-butyl ester 在 lithium aluminium tetrahydride 、 sodium acetate 、 三氟乙酸 作用下， 以 乙醚 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 4.84h， 生成 1(S)-4'(S)-pyrrol-1-yl-4'-(1,2,3,4-tetrahydro-1H-β-carbolin-1-yl)butyric acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of Tetrahydro-β-carbolines and Studies of the Pictet–Spengler Reaction

  摘要：

  Tetrahydro-beta-carbolines have been prepared in a diastereomerically pure form by a short, efficient synthetic sequence consisting of reaction of cl-aminoaldehydes with tryptamine. A study was made of the major factors affecting the stereoselectivity of the Pictet-Spengler reaction. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00165-4
• 作为产物：
  描述：

  N-苄氧羰基-L-谷氨酸γ-叔丁酯 在 palladium on activated charcoal N-甲基吗啉 、 ammonium formate 、 氯甲酸异丁酯 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 4(S)-amino-4-(methoxymethylcarbamoyl)butyric acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of Tetrahydro-β-carbolines and Studies of the Pictet–Spengler Reaction

  摘要：

  Tetrahydro-beta-carbolines have been prepared in a diastereomerically pure form by a short, efficient synthetic sequence consisting of reaction of cl-aminoaldehydes with tryptamine. A study was made of the major factors affecting the stereoselectivity of the Pictet-Spengler reaction. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00165-4

文献信息

• 2-oxothiazole compounds and method of using same for chronic inflammatory disorders
  申请人：Kokotos George

  公开号：US09597318B2

  公开（公告）日：2017-03-21

  The invention provides compounds of formula (I) wherein X is O or S; R1 is H, OH, SH, nitro, NH2, NHC1-6alkyl, N(C1-6alkyl)2, halo, haloC1-6alkyl, CN, C1-6-alkyl, OC1-6alkyl, C1-6alkylCOOH, C1-6alkylCOOC1-6alkyl, C2-6-alkenyl, C3-10cycloalkyl, C6-10aryl, C1-6alkylC6-10aryl, heterocyclyl, heteroaryl, CONH2, CONHC1-6alkyl, CON(C1-6alkyl)2, OCOC1-6alkyl, or is an acidic group, such as a group comprising a carboxyl, phosphate, phosphinate, sulfate, sulfonate, or tetrazolyl group; R2 is as defined for R1 or R1 and R2 taken together can form a 6-membered aromatic ring optionally substituted by up to 4 groups R5; R3 is H, halo (preferably fluoro), or CHal3 (preferably CF3); each R5 is defined as for R1; V1 is a covalent bond, —O—, or a C1-20alkyl group, or C2-20-mono or multiply unsaturated alkenyl group; said alkyl or alkenyl groups being optionally interrupted by one or more heteroatoms selected from O, NH, N(C1-6 alkyl), S, SO, or SO2; M1 is absent or is a C5-10 cyclic group or a C5-15 aromatic group; and R4 is H, halo, OH, CN, nitro, NH2, NHC1-6alkyl, N(C1-6alkyl)2, haloC1-6alkyl, a C1-20alkyl group, or C2-20-mono or multiply unsaturated alkenyl group, said C1-20alkyl or C2-20alkenyl groups being optionally interrupted by one or more heteroatoms selected from O, NH, N(C1-6 alkyl), S, SO, or SO2; with the proviso that the group V1M1R4 as a whole provides at least 4 backbone atoms from the C(R3) group; or a salt, ester, solvate, N-oxide, or prodrug thereof; for use in the treatment of a chronic inflammatory condition.

  该发明提供了以下式（I）的化合物，其中X为O或S；R1为H、OH、SH、硝基、NH2、NHC1-6烷基、N（C1-6烷基）2、卤素、卤代C1-6烷基、CN、C1-6烷基、OC1-6烷基、C1-6烷基COOH、C1-6烷基COOC1-6烷基、C2-6烯基、C3-10环烷基、C6-10芳基、C1-6烷基C6-10芳基、杂环烷基、杂芳基、CONH2、CONHC1-6烷基、CON（C1-6烷基）2、OCOC1-6烷基，或者是酸性基团，例如包含羧基、磷酸基、磷酸酯基、硫酸基、磺酸基或四唑基团的基团；R2如R1定义或R1和R2一起形成一个6-成员芳香环，可选地由多达4个R5基团取代；R3为H、卤素（优选氟素），或CHal3（优选CF3）；每个R5如R1定义；V1为共价键，—O—，或C1-20烷基，或C2-20单烯或多不饱和烯基；所述烷基或烯基基团可选地由O、NH、N（C1-6烷基）、S、SO或SO2中选择的一个或多个杂原子中断；M1不存在或为C5-10环烷基或C5-15芳基；R4为H、卤素、OH、CN、硝基、NH2、NHC1-6烷基、N（C1-6烷基）2、卤代C1-6烷基、C1-20烷基，或C2-20单烯或多不饱和烯基，所述C1-20烷基或C2-20烯基基团可选地由O、NH、N（C1-6烷基）、S、SO或SO2中选择的一个或多个杂原子中断；但条件是，V1M1R4作为一个整体至少提供来自C（R3）基团的4个骨架原子；或其盐、酯、溶剂化合物、N-氧化物或前药；用于治疗慢性炎症症状。