(3S,5S,6R)-4-(tert-butyloxycarbonyl)-5,6-diphenyl-3-(2'-propenyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one | 112741-54-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (3S,5S,6R)-4-(tert-butyloxycarbonyl)-5,6-diphenyl-3-(2'-propenyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one
• 英文别名: (3S,5S,6R)-4-(tert-butyloxycarbonyl)-5,6-diphenyl-3-(1'-prop-2'-enyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one；Tert-butyl (3s,5s,6r)-3-allyl-2-oxo-5,6-diphenylmorpholine-4-carboxylate；tert-butyl (3S,5S,6R)-2-oxo-5,6-diphenyl-3-prop-2-enylmorpholine-4-carboxylate
• CAS: 112741-54-5
• 化学式: C₂₄H₂₇NO₄
• 分子量: 393.483
• InChiKey: JFYVSCSGKFZNON-PCCBWWKXSA-N

物化性质

• 熔点：
  177-178 °C
• 沸点：
  533.5±50.0 °C(Predicted)
• 密度：
  1.124±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,5S,6R)-4-(tert-butyloxycarbonyl)-5,6-diphenyl-3-(2'-propenyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one 在 氨 、 lithium 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 以70%的产率得到Boc-L-烯丙基甘氨酸
  参考文献：
  名称：

  α-氨基酸的不对称合成：N-BOC-5、6-二苯基-2,3,5,6-四氢-4h-1,4-恶嗪-2-酮的烯醇盐与阳离子官能化的比较

  摘要：

  手性甘氨酸盐1和2的烯醇盐生成和随后的烷基化以高度非对映选择性发生。减少同源产物（3和4）提供了高对映体过量，Nt-BOC和游离α-氨基酸衍生物5和6。

  DOI：

  10.1016/s0040-4039(00)82268-6
• 作为产物：
  描述：

  (1'S,2'R)-ethyl N-(tert-butyloxycarbonyl)-N-(1',2'-diphenyl-2'-hydroxyethyl)glycinate 在 N-溴代丁二酰亚胺(NBS) 、 对甲苯磺酸 、 calcium chloride 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 四氯化碳 、 苯 为溶剂， 反应 13.0h， 生成 (3S,5S,6R)-4-(tert-butyloxycarbonyl)-5,6-diphenyl-3-(2'-propenyl)-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one
  参考文献：
  名称：

  Practical asymmetric syntheses of .alpha.-amino acids through carbon-carbon bond constructions on electrophilic glycine templates

  摘要：

  DOI：

  10.1021/ja00213a031

文献信息

• Novel bicyclic cyanoheterocycles, process for their preparation and their use as medicaments
  申请人：Wagner Holger

  公开号：US20050059716A1

  公开（公告）日：2005-03-17

  The invention relates to compounds of the formula I in which the radicals have the stated meanings, their stereoisomeric forms and their physiologically tolerated salts and process for their preparation. The compounds are suitable for the treatment of metabohlic disorders such as type 2 diabetes.

  本发明涉及公式I的化合物，其中基团具有所述的含义，它们的立体异构体形式和其生理上可耐受的盐以及它们的制备过程。这些化合物适用于治疗代谢性疾病，如2型糖尿病。
• Bicyclic cyanoheterocycles, process for their preparation and their use as medicaments
  申请人：Sanofi-Aventis Deutschland GmbH

  公开号：US07008957B2

  公开（公告）日：2006-03-07

  The invention relates to compounds of the formula I in which the radicals have the stated meanings, their stereoisomeric forms and their physiologically tolerated salts and process for their preparation. The compounds are suitable for the treatment of metabohlic disorders such as type 2 diabetes.

  本发明涉及式I化合物，其中基团具有所述含义，它们的立体异构体形式和其生理上耐受的盐以及制备它们的过程。这些化合物适用于治疗代谢性疾病，如2型糖尿病。
• Asymmetric synthesis of monosubstituted and .alpha.,.alpha.-disubstituted .alpha.-amino acids via diastereoselective glycine enolate alkylations
  作者：Robert M. Williams、Myeong Nyeo Im

  DOI：10.1021/ja00024a038

  日期：1991.11

  The enolates derived from the optically active (5S,6R)- and (5R,6S)-4(tert-butyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one (1a,b) and (5S,6R)- and (5R,6S)-4-(benzyloxycarbonyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-ones (2a,b) efficiently couple with alkyl halides to afford the corresponding anti-alpha-monosubstituted oxazinones (3 and 4). The enolate alkylation of the alpha-monosubstituted oxazinones (3 and 4) provides the corresponding alpha,alpha-disubstituted oxazinones (7 and 8). Dissolving-metal reduction of the homologated oxazinones allows the direct preparation of t-BOC-protected alpha-amino acids. In the case of a dissolving-metal-reducible functionality, hydrogenation over a Pd0 catalyst furnishes the zwitterionic amino acids. By employing this protocol several amino acids or their corresponding N-t-BOC derivatives, such as allylglycine, alanine, phenylalanine, beta-ethylaspartic acid, alpha-methylphenylalanine, N-(tert-butyloxycarbonyl)dimethallylglycine, N-(tert-butyloxycarbonyl)-2-(2'-propenyl)norvaline, N-(tert-butyloxycarbonyl)-2-(3'-methyl-2'-butenyl)alanine, N-(tert-butyloxycarbonyl)-2-(2'-propenyl)alanine, 2-(3'-phenylpropyl)alanine, 2-amino-6-(acetyloxy)hexanoic acid, and 2(tert-butyloxycarbonyl)amino-6-[(p-methoxybenzyl)thio]hexanoic acid, are prepared in high enantiomeric excess.
• WILLIAMS, ROBERT M.;SINCLAIR, PETER J.;ZHAI, DONGGUAN;CHEN, DAIMO, J. AMER. CHEM. SOC., 110,(1988) N 5, 1547-1557
  作者：WILLIAMS, ROBERT M.、SINCLAIR, PETER J.、ZHAI, DONGGUAN、CHEN, DAIMO

  DOI：——

  日期：——
• WILLIAMS, ROBERT M.;IM, MYEONG-NYEO, TETRAHEDRON LETT., 29,(1988) N 47, C. 6075-6078
  作者：WILLIAMS, ROBERT M.、IM, MYEONG-NYEO

  DOI：——

  日期：——