(5R)-3,4,5,6-四氢-5-苯基-4(H)-1,4-恶嗪-2-酮 | 121269-45-2

• 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
• 中文名称: (5R)-3,4,5,6-四氢-5-苯基-4(H)-1,4-恶嗪-2-酮
• 中文别名: (R)-5-苯基吗啉-2-酮
• 英文名称: (R)-5-phenyl-3,4,5,6-tetrahydro-2H-1,4-oxazin-2-one
• 英文别名: (5R)-5-phenyl-3,4,5,6-tetrahydro-1,4-oxazin-2-one；(5R)-5-phenyl-1,4-oxazin-2-one；(R)-5-phenylmorpholin-2-one；(5R)-5-phenylmorpholin-2-one
• CAS: 121269-45-2
• 化学式: C₁₀H₁₁NO₂
• mdl: MFCD00269692
• 分子量: 177.203
• InChiKey: CMYHFJFAHHKICH-VIFPVBQESA-N

物化性质

• 熔点：
  53.5-54.5 °C
• 沸点：
  364.3±42.0 °C(Predicted)
• 密度：
  1.149±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  (5R)-3,4,5,6-四氢-5-苯基-4(H)-1,4-恶嗪-2-酮 在 sodium hexamethyldisilazane 、 三乙胺 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 反应 14.0h， 生成 (3S,5R)-2,3,5,6-tetrahydro-3-(n-butyl)-5-phenyl-N-(tert-butyloxycarbonyl)-4H-1,4-oxazin-2-one
  参考文献：
  名称：

  Enantioselective synthesis of .alpha.-amino acid derivatives via the stereoselective alkylation of a homochiral glycine enolate synthon

  摘要：

  DOI：

  10.1021/jo00277a032
• 作为产物：
  描述：

  (R)-2-methyl-4-phenyl-Δ²-oxazoline 在 palladium on activated charcoal selenium(IV) oxide 、 氢气 作用下， 以 1,4-二氧六环 、 乙酸乙酯 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 5.0h， 生成 (5R)-3,4,5,6-四氢-5-苯基-4(H)-1,4-恶嗪-2-酮
  参考文献：
  名称：

  Oxidative Rearrangement of 2-Substituted Oxazolines. A Novel Entry to 5,6-Dihydro-2H-1,4-oxazin-2-ones and Morpholin-2-ones

  摘要：

  A novel synthesis of 5,6-dihydro-2H-1,4-oxazin-2-ones by SeO2-promoted oxidative rearrangement of 2-alkyl- and 2-(arylmethyl)oxazolines is described. Yields are good to excellent; (up to 94%) with the highest yields obtained for 2-arylmethyl- and 2-neopentyl-substituted oxazolines. This reaction provides convenient access to novel 5-aryl-substituted dihydrooxazinones in high yield. The latter compounds are important ''chiral glycine'' synthons for asymmetric synthesis of a-amino acids. Since oxazolines are readily derived from carboxylic acids or their equivalents, this oxidative rearrangement constitutes an entry to synthesis of a-amino acids from carboxylic acids. A mechanism is proposed to account for the rearrangement involving a ''nitrilium to acylium'' 1,2-migration.

  DOI：

  10.1021/jo952144f

文献信息

• Synthesis of UDP-glucose: N-acylsphingosine glucosyltransferase inhibitors
  申请人：Genzyme Corporation

  公开号：US20030050299A1

  公开（公告）日：2003-03-13

  Disclosed is a novel enantiomeric synthesis cermamide-like inhibitors of UDP-glucose: N-acylsphingosine glucosyltransferase. Also disclosed are novel intermediates formed during the synthesis.

  披露了一种新型对映合成UDP葡萄糖：N-酰基鞘氨醇葡糖转移酶抑制剂的方法。同时还披露了在合成过程中形成的新型中间体。
• [EN] HEPATITIS C VIRUS INHIBITORS<br/>[FR] INHIBITEURS DU VIRUS DE L'HÉPATITE C
  申请人：ENANTA PHARM INC

  公开号：WO2015017382A1

  公开（公告）日：2015-02-05

  The present invention discloses compounds of Formula (I), and pharmaceutically acceptable salts, esters, or prodrugs thereof: (structurally represented), which inhibit RNA-containing virus, particularly the hepatitis C virus (HCV). Consequently, the compounds of the present invention interfere with the life cycle of the hepatitis C virus and are also useful as antiviral agents. The present invention further relates to pharmaceutical compositions comprising the aforementioned compounds for administration to a subject suffering from HCV infection. The invention also relates to methods of treating an HCV infection in a subject by administering a pharmaceutical composition comprising the compounds of the present invention.

  本发明公开了化合物的结构式(I)及其药学上可接受的盐、酯或前药：（结构表示），这些化合物抑制RNA含量病毒，特别是丙型肝炎病毒（HCV）。因此，本发明的化合物干扰丙型肝炎病毒的生命周期，并且也可用作抗病毒剂。本发明还涉及包括上述化合物的药物组合物，用于治疗患有HCV感染的受试者。该发明还涉及通过给予包含本发明化合物的药物组合物来治疗受试者的HCV感染的方法。
• Stereoselective alkylation of chiral glycine enolate synthons. The enantioselective synthesis of α-amino acid derivatives.
  作者：Joseph F. Dellaria、D.Santarsiero Bernard

  DOI：10.1016/s0040-4039(00)82269-8

  日期：——

  The highly stereoselective alkylation (% de=99.6 to 97.6) of a new chiral glycine enolate synthon derived from D-2-phenylglycinol is described. Deprotection of the alkylation adducts in a one-pot three-step procedure provides the ethyl ester hydrochloride salts of the corresponding α-amino acids with no attending racemization.

  描述了衍生自D-2-苯基甘氨醇的新的手性甘氨酸烯醇式合成子的高度立体选择性烷基化（％de = 99.6至97.6）。用一锅三步法对烷基化加合物进行脱保护，即可得到相应的α-氨基酸的乙酯盐酸盐，而不会发生外消旋作用。
• Preparation of enantiopure long chain <i>threo</i>-2-amino-3-hydroxyesters via chiral morpholinone-derived azomethine ylids
  作者：Victoria A Brome、Laurence M Harwood、Helen MI Osborn

  DOI：10.1139/v06-121

  日期：2006.10.1

  The synthetic approach to threo-2-amino-3-hydroxyesters possessing long alkyl chains outlined herein centres on the generation of chiral azomethine ylids by reaction of (5R)-5-phenyl-morpholin-2-one, (R)-(1), with long chain aldehydes. In the presence of a second equivalent of aldehyde, the azomethine ylid can be trapped to afford a cycloadduct with three new stereodefined centres. Degradation of the cycloadduct allows entry to β-substituted-α-amino acid derivatives, which have potential as building blocks for sphingosine synthesis.Key words: sphingosine, morpholinone, chiral azomethine ylid, dipolar cycloaddition.

  本文概述的具有长烷基链的苏-2-氨基-3-羟基酯的合成方法主要是通过 (5R)-5-苯基-吗啉-2-酮 (R)-(1) 与长链醛反应生成手性氮甲基。在第二种等量醛的存在下，偶氮甲基吡啶可被俘获，生成具有三个新立体中心的环加合物。环加成物的降解过程可进入 β-取代-α-氨基酸衍生物，这些衍生物有可能成为合成鞘磷脂的构建基块。
• Double diastereocontrol in the synthesis of enantiomerically pure polyoxamic acid
  作者：Laurence M. Harwood、Sarah M. Robertson

  DOI：10.1039/a807471b

  日期：——

  Polyoxamic acid 4 is prepared by a short and efficient process involving diastereochemically matched cycloaddition of 5-(S)-phenylmorpholin-2-one 1 with (S)-glyceraldehyde acetonide 2, followed by sequential hydrolysis and hydrogenolysis of the adduct.

  聚氧肟酸 4 的制备过程简短而高效，先将 5-(S)-苯基吗啉-2-酮 1 与 (S)- 乙醛缩丙酮 2 进行非对映化学匹配环加成，然后依次对加成物进行水解和氢解。