(2R,3S)-3,4-二甲基-2-苯基-1,4-氧杂氮杂环庚烷-5,7-二酮 | 67376-72-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧氮杂卓类
• 中文名称: (2R,3S)-3,4-二甲基-2-苯基-1,4-氧杂氮杂环庚烷-5,7-二酮
• 英文名称: (2R,3S)-3,4-dimethyl-2-phenylperhydro-1,4-oxazepine-5,7-dione
• 英文别名: (2S,3S)-3,4-dimethyl-2-phenyl-[1,4]oxazepane-5,7-dione；(2R,3S)-3,4-Dimethyl-2-phenyl-1,4-oxazepan-5,7-dion；N,3S-dimethyl-2R-phenylhexahydro-1,4-oxazepine；(2R,3S)-3,4-dimethyl-2-phenyl-1,4-oxazepane-5,7-dione
• CAS: 67376-72-1
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: VWGLSJADRJXISE-ZANVPECISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3S)-3,4-二甲基-2-苯基-1,4-氧杂氮杂环庚烷-5,7-二酮 在 对甲苯磺酰叠氮 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以85%的产率得到(2R,3S)-(-)-6-Diazo-3,4-dimethyl-2-phenyl-1,4-oxazepan-5,7-dion
  参考文献：
  名称：

  Chelucci, Giorgio; Saba, Antonio, Angewandte Chemie, 1995, vol. 107, # 1, p. 104 - 106

  摘要：

  DOI：
• 作为产物：
  描述：

  甲基丙二酸氢 、 麻黄碱 以40%的产率得到(2R,3S)-3,4-二甲基-2-苯基-1,4-氧杂氮杂环庚烷-5,7-二酮
  参考文献：
  名称：

  Tietze, Lutz-F.; Brand, Siegbert; Pfeiffer, Thomas, Angewandte Chemie, 1985, vol. 97, # 9, p. 790 - 791

  摘要：

  DOI：

文献信息

• ASYMMETRIC TOTAL SYNTHESIS OF INDOLMYCIN
  作者：Takeshi Takeda、Teruaki Mukaiyama

  DOI：10.1246/cl.1980.163

  日期：1980.2.5

  An asymmetric total synthesis of indolmycin was achieved via a key intermediate, α-indolmycenic acid ester. The ester was obtained by oxygenation of methyl (S)-3-(3-indolyl)butanoate which was prepared by asymmetric synthesis utilizing (2R,3S)-3,4-dimethyl-2-phenylperhydro-l,4-oxazepine-5,7-dione. (2S,3R)-N-[2-Hydroxy-3-(3-indolyl)-butanoyl]-N′-methylthiourea prepared from α-indolmycenic acid ester

  吲哚霉素的不对称全合成是通过关键中间体 α-吲哚霉素酸酯实现的。该酯是通过使用 (2R,3S)-3,4-二甲基-2-苯基全氢-1,4-氧氮杂-5 不对称合成制备的 (S)-3-(3-吲哚基) 丁酸甲酯氧化获得的,7-二酮。(2S,3R)-N-[2-Hydroxy-3-(3-indolyl)-butanoyl]-N'-methylthiourea 由 α-indolmycenicate 制备，用 2-chlorobenzoxazolium 盐处理得到光学纯度为 93% 的吲哚霉素.
• THE ASYMMETRIC MICHAEL REACTION OF (2<i>R</i>,3<i>S</i>)-3,4-DIMETHYL-2-PHENYLPERHYDRO-1,4-OXAZEPINE-5,7-DIONE WITH 1-NITROCYCLOHEXENE
  作者：Takeshi Takeda、Tomonori Hoshiko、Teruaki Mukaiyama

  DOI：10.1246/cl.1981.797

  日期：1981.6.5

  Optically active (2-nitrocyclohexyl)acetic acid(III) was obtained by the Michael reaction of (2R,3S)-3,4-dimethyl-2-phenylperhydro-1,4-oxazepine-5,7-dione(I) with 1-nitrocyclohexene in the presence of potassium t-butoxide (or cesium fluoride) and crown ether, followed by acid hydrolysis.

  通过（2R,3S）-3,4-二甲基-2-苯基-1,4-氧氮杂卓-5,7-二酮（I）与1-硝基环己烯在叔丁醇钾（或氟化铯）和冠醚存在下发生迈克尔反应，然后进行酸水解，得到光学活性（2-硝基环己基）乙酸（III）。
• Asymmetric total synthesis from cyclopentene-1,2-diones: Characterisation of a diastereomerically pure michael adduct
  作者：Richard T. Brown、Mark J. Ford

  DOI：10.1016/s0040-4039(00)88907-8

  日期：1990.1

  A key cyclopentenolone intermediate in the asymmetric synthesis of alkaloids and seco-iridoids has been prepared from reaction of a chiral 5, 7-dioxoperhydro-1,4-oxazepine with a cyclopentene-1,2-dione dimer; the absolute configuration at the induced chiral centres has been assigned from n.O.e. experiments.

  已从手性5、7-二氧杂氢-1,4-氧杂氮平与环戊烯-1,2-二酮二聚体的反应中制备了生物碱和癸二糖苷类化合物不对称合成中的关键环戊烯酮中间体。诱导手性中心的绝对构型已由nOe实验确定。
• Asymmetric syntheses of a GPR40 receptor agonist via diastereoselective and enantioselective conjugate alkynylation
  作者：Jacqueline C.S. Woo、Sheng Cui、Shawn D. Walker、Margaret M. Faul

  DOI：10.1016/j.tet.2010.04.019

  日期：2010.6

  Two asymmetric methods to synthesize a potent GPR40 receptor agonist are reported. Both synthetic routes utilize readily available, inexpensive starting materials and reagents. The first route relies on a highly diastereoselective conjugate alkynylation of an ephedrine-derived oxazepanedione acceptor. The second route features the enantioselective alkynylation of a Meldrum's acid-derived acceptor mediated by a chiral zinc cinchonidine reagent. (C) 2010 Elsevier Ltd. All rights reserved.
• Brown, Richard T.; Ford, Mark J., Synthetic Communications, 1988, vol. 18, # 15, p. 1801 - 1806
  作者：Brown, Richard T.、Ford, Mark J.

  DOI：——

  日期：——