(4S,5S)-4-hydroxymethyl-5-phenyloxazolidin-2-one | 146985-90-2

• 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,5S)-4-hydroxymethyl-5-phenyloxazolidin-2-one
• 英文别名: (4S,5S)-4-hydroxymethyl-5-phenyloxazolidin；(4S,5S)-4-Hydroxymethyl-5-phenyl-oxazolidin-2-one；(4S,5S)-4-(hydroxymethyl)-5-phenyl-1,3-oxazolidin-2-one
• CAS: 146985-90-2
• 化学式: C₁₀H₁₁NO₃
• 分子量: 193.202
• InChiKey: VUTZOFOFUVLOLO-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S,5S)-4-hydroxymethyl-5-phenyloxazolidin-2-one 在 吡啶 、 4-二甲氨基吡啶 、 氢氧化钾 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 64.0h， 生成 L-threo-2-amino-3-morpholino-1-phenylpropan-1-ol
  参考文献：
  名称：

  Glycosyltransferase Inhibitors:  Synthesis of d-threo-PDMP, l-threo-PDMP, and Other Brain Glucosylceramide Synthase Inhibitors from d- or l-Serine

  摘要：

  The synthesis of enantiomerically pure (1S,2S)-1-phenyl-2-decanoylamino-3-N-morpholino-1- propanol (L-threo-PDMP) (la) from L-serine, and the enantiomer (1R,2R)-1-phenyl-2-decanoylamino-3-morpholino-1-propanol (D-threo-PDMP] (Ib) from D-serine is reported. Reductive alkylation of the fully protected O'Donnell's Schiff base (3b) derived from D-serine provided the beta-amino alcohol 5b in high yield and excellent selectivity, which yielded optically pure Ib in high yield after six steps. Three other D-threo-PDMP analogues with various amine groups have been synthesized using the same methodology, including the more potent pyrrolidine compound D-threo-PDPP (le). A key feature of the synthesis is the isolation of tosylate (8b), which allows for the divergent synthesis of many analogues from a common advanced intermediate. The synthesis is amenable to large-scale production of D-threo-PDMP, L-threo-PDMP, and similar compounds.

  DOI：

  10.1021/jo980951j
• 作为产物：
  描述：

  (4S,5S)-4-hydroxymethyl-5-phenyloxazolidine-2-thione 在 sodium hydroxide 、 双氧水 作用下， 以 水 为溶剂， 以22%的产率得到(4S,5S)-4-hydroxymethyl-5-phenyloxazolidin-2-one
  参考文献：
  名称：

  Moreno-Manas, Marcial; Padros, Imma, Journal of Heterocyclic Chemistry, 1993, vol. 30, # 5, p. 1235 - 1240

  摘要：

  DOI：

文献信息

• Synthesis of All Stereoisomers and Some Congeners of Isocytoxazone
  作者：Vitomir Šunjić、Zdenko Hameršak、Dragan Šepac、Dinko Žiher

  DOI：10.1055/s-2003-37353

  日期：——

  cis-Isocytoxazone 2a and trans-isocytoxazone 2h, structural isomers of the antiasthmatic agent cytoxazone (-)-1, and their 5-substituted congeners 23-28 have been prepared. Aldol reaction of para-substituted benzaldehydeswith 7-chloro-1-methyl-5-phenyl-1,4-benzodiazepin-2-one, followed by separation of diastereomeric racemates afforded 3-10. Acid-catalyzed 1,4-benzodiazepine ring opening, and transformation

  已制备顺式-异胞嘧啶2a和反式-异胞嘧啶2h，抗哮喘药胞嘧啶(-)-1的结构异构体，以及它们的5-取代同系物23-28。对位取代的苯甲醛与 7-chloro-1-methyl-5-phenyl-1,4-benzodiazepin-2-one 进行羟醛反应，然后分离非对映体外消旋物，得到 3-10。酸催化的 1,4-苯并二氮杂环开环，以及通过 1,3-恶唑烷-2-酮的 4-甲氧基羰基衍生物转化 β-芳基-β-羟基-α-氨基酸 (11-16) 的甲酯(17-22) 和它们的还原提供了目标 oxazolidin-2-one 衍生物 23-28。外消旋异环唑酮 2a 和 2b 由 4-甲氧基苯乙烯环氧化物通过独立路线制备。这些非对映体外消旋体的纯对映体通过 HPLC 色谱在手性固定相上进行分离。
• Oxazolidin-2-one-Pyrimidine Derivatives
  申请人：Fairhurst Robin Alec

  公开号：US20140135330A1

  公开（公告）日：2014-05-15

  The present invention relates to oxazolidin-2-one substituted pyrimidine compounds that act as PI3K (phosphatidylinositol-3-kinase) inhibitors, as well as pharmaceutical compositions thereof, methods for their manufacture and uses for the treatment of conditions, diseases and disorders dependent on PI3K.

  本发明涉及取代嘧啶的噁唑烷-2-酮化合物，其作为PI3K（磷脂酰肌醇-3-激酶）抑制剂，以及其药用组合物、制备方法和用于治疗依赖于PI3K的疾病、症状和疾病的用途。
• Conjugate addition of chloride to α,β-unsaturated chiral imides promoted by BCl₃-derivatives. A synthesis of 3-chlorobutanoic acid
  作者：Giuliana Cardillo、Angela de Simone、Luca Gentilucci、Claudia Tomasini

  DOI：10.1039/c39940000735

  日期：——

  The conjugate addition of chloride to chiral but-2-enoic imides promoted by BCl3-derivatives proceeds with diastereoisomeric ratios of up to 90 : 10 and affords the corresponding 3-chlorobutanoic imides from which, after mild hydrolysis, the 3-chlorobutanoic acid is obtained.

  在BCl3衍生物的催化下，氯化物与手性丁-2-烯酰亚胺的共轭加成反应，其非对映异构体比率高达90:10，并生成相应的3-氯丁酰亚胺，经温和水解后，可得到3-氯丁酸。
• OXAZOLIDIN-2-ONE-PYRIMIDINE DERIVATIVES AND THE USE THEREOF AS PHOSPHATIDYLINOSITOL-3-KINASE INHIBITORS
  申请人：Fairhurst Robin Alec

  公开号：US20160168145A1

  公开（公告）日：2016-06-16

  The present invention relates to oxazolidin-2-one substituted pyrimidine compounds that act as PI3K (phosphatidylinositol-3-kinase) inhibitors, as well as pharmaceutical compositions thereof, methods for their manufacture and uses for the treatment of conditions, diseases and disorders dependent on PI3K.

  本发明涉及氧杂环丙烷-2-酮取代嘧啶化合物，其作为PI3K（磷脂酰肌醇-3-激酶）抑制剂，以及其制药组合物，其制备方法和用于治疗依赖于PI3K的疾病、疾病和障碍的用途。
• Oxazolidin-2-one-pyrimidine derivative and use thereof for the treatment of conditions, diseases and disorders dependent upon PI3 kinases
  申请人：Fairhurst Robin Alec

  公开号：US09296733B2

  公开（公告）日：2016-03-29

  The present invention relates to oxazolidin-2-one substituted pyrimidine compounds that act as PI3K (phosphatidylinositol-3-kinase) inhibitors, as well as pharmaceutical compositions thereof, methods for their manufacture and uses for the treatment of conditions, diseases and disorders dependent on PI3K.

  本发明涉及一种氧杂环丙烷-2-酮取代嘧啶化合物，其作为PI3K（磷脂酰肌醇-3-激酶）抑制剂，以及其制药组合物、制备方法和用于治疗依赖于PI3K的疾病、病症和疾患的用途。