(4R,5S)-4,5-Dihydro-5-methyl-2-phenyloxazol-4-carbonsaeure-methylester | 154005-98-8

• 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: (4R,5S)-4,5-Dihydro-5-methyl-2-phenyloxazol-4-carbonsaeure-methylester
• 英文别名: methyl (R,S)-2-phenyl-2-oxazoline-5-methyl-4-carboxylate；methyl (4R,5S)-5-methyl-2-phenyl-4,5-dihydro-1,3-oxazole-4-carboxylate
• CAS: 154005-98-8
• 化学式: C₁₂H₁₃NO₃
• 分子量: 219.24
• InChiKey: YBKQIWQAEPMIFG-WCBMZHEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R,5S)-4,5-Dihydro-5-methyl-2-phenyloxazol-4-carbonsaeure-methylester 在 盐酸 作用下， 生成 D-别苏氨酸
  参考文献：
  名称：

  固液PTC条件下α-氨基酸酯的N-单烷基化

  摘要：

  N-(2-硝基苯磺酰基)-(o-NBS-AA-OMe, 4) 和 N-(4-硝基苯磺酰基)-α-氨基酸甲酯 (p-NBS-AA-OMe, 5) 用多种烷基卤化物 6 在固液相转移催化 (SL-PTC) 条件下，得到烷基化产物 o-NBS-N-R2-AA-OMe 7 和 p-NBS-N-R2-AA-OMe 8在没有任何可检测到的外消旋化的情况下以优异的产量获得

  DOI：

  10.1002/(sici)1099-0690(200004)2000:8<1443::aid-ejoc1443>3.0.co;2-5
• 作为产物：
  描述：

  苯甲酰基-d-苏氨酸甲酯 在 氯化亚砜 作用下， 生成 (4R,5S)-4,5-Dihydro-5-methyl-2-phenyloxazol-4-carbonsaeure-methylester
  参考文献：
  名称：

  固液PTC条件下α-氨基酸酯的N-单烷基化

  摘要：

  N-(2-硝基苯磺酰基)-(o-NBS-AA-OMe, 4) 和 N-(4-硝基苯磺酰基)-α-氨基酸甲酯 (p-NBS-AA-OMe, 5) 用多种烷基卤化物 6 在固液相转移催化 (SL-PTC) 条件下，得到烷基化产物 o-NBS-N-R2-AA-OMe 7 和 p-NBS-N-R2-AA-OMe 8在没有任何可检测到的外消旋化的情况下以优异的产量获得

  DOI：

  10.1002/(sici)1099-0690(200004)2000:8<1443::aid-ejoc1443>3.0.co;2-5

文献信息

• Materials and methods for the treatment of diabetes, hyperlipidemia, hypercholesterolemia, and atherosclerosis
  申请人：ARYX Therapeutics

  公开号：US06768008B2

  公开（公告）日：2004-07-27

  The subject invention provides pharmaceutical compounds useful in the treatment of Type II diabetes. These compounds are advantageous because they are readily metabolized by the metabolic drug detoxification systems. Particularly, thiazolidinedione analogs that have been designed to include esters within the structure of the compounds are provided. This invention is also drawn to methods of treating disorders, such as diabetes, comprising the administration of therapeutically effective compositions comprising compounds that have been designed to be metabolized by serum or intracellular hydrolases and esterases. Pharmaceutical compositions of the ester-containing thiazolidinedione analogs are also taught.

  该发明提供了在治疗2型糖尿病中有用的药物化合物。这些化合物具有优势，因为它们可以被代谢药物解毒系统迅速代谢。特别地，设计了包含酯基的噻唑烷二酮类似物的化合物。该发明还涉及治疗疾病的方法，如糖尿病，包括给予经设计为能够被血清或细胞内水解酶和酯酶代谢的化合物的治疗有效组合物。还教授了含酯基的噻唑烷二酮类似物的药物组合物。
• Benzamide bioisosteres incorporating dihydroheteroazole substructures: EPC synthesis and SAR leading to a selective dopamine D4 receptor partial agonist (FAUC 179)
  作者：Jürgen Einsiedel、Harald Hübner、Peter Gmeiner

  DOI：10.1016/s0960-894x(01)00484-x

  日期：2001.9

  Conformationally restricted benzamide bioisosteres were investigated when the chiral phenyldihydroimidazole derivative 4e (FAUC 179) showed strong and highly selective dopamine D4 receptor binding (K(i)high=0.95nM). Mitogenesis experiments indicated partial agonist properties (42%). EPC syntheses of the target compounds of type 4 were performed starting from alpha-amino acids.

  当手性苯基二氢咪唑衍生物4e（FAUC 179）表现出强而高度选择性的多巴胺D4受体结合（K（i）high = 0.95nM）时，研究了构象受限的苯甲酰胺生物异构体。有丝分裂实验表明部分激动剂性质（42％）。从α-氨基酸开始进行类型4的目标化合物的EPC合成。
• AsymmetrischeMichael-Additionen. Stereoselektive Alkylierung chiraler, nicht racemischer Enolate durch Nitroolefine. Herstellung enantiomerenreiner ?-Aminobutters�ure- und Bernsteins�ure-Derivate
  作者：Giorgio Calderari、Dieter Seebach

  DOI：10.1002/hlca.19850680611

  日期：1985.9.25

  Asymmetric Michael-Additions. Stereoselective Alkylation of Chiral, Non-racemic Enolates by Nitroolefins. Preparation of Enantiomerically Pure γ-Aminobutyric and Succinic Acid Derivatives

  不对称迈克尔-加法。硝基烯烃对手性，非外消旋烯醇的立体选择性烷基化反应。对映体纯的γ-氨基丁酸和琥珀酸衍生物的制备
• An enantioselective synthesis of (6R)-lactacystin
  作者：E.J. Corey、Soongyu Choi

  DOI：10.1016/s0040-4039(00)61573-3

  日期：1993.10

  The first enantiospecific, stereocontrolled total synthesis of (6R)-lactacystin, a potential neurotrophic agent, is described.

  描述了第一个对映体特异性，立体控制的（6R）-lactacystin，一种潜在的神经营养剂的总合成。
• Cytotoxic agents and methods of use
  申请人：Xiao Xiao-Yi

  公开号：US20080161282A1

  公开（公告）日：2008-07-03

  Disclosed are compounds that inhibit proteasomic activity in cells. Also disclosed are pharmaceutical compositions comprising such compounds as well as methods to treat conditions, particularly cell proliferative conditions, such as cancer and inflammatory conditions.