(4S,5S)-5-allyl-4-methoxy-2-oxazolidinone | 115246-57-6

• 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)-5-allyl-4-methoxy-2-oxazolidinone
• 英文别名: trans-5-allyl-4-methoxy-2-oxazolidinone；(4S,5S)-5-allyl-4-methoxy-2-oxazylidone；(4S,5S)-4-methoxy-5-prop-2-enyl-1,3-oxazolidin-2-one
• CAS: 115246-57-6
• 化学式: C₇H₁₁NO₃
• 分子量: 157.169
• InChiKey: QYWAVRDICZEAFN-WDSKDSINSA-N

物化性质

• 熔点：
  50.5 °C
• 沸点：
  322.5±31.0 °C(predicted)
• 密度：
  1.12±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S,5S)-5-allyl-4-methoxy-2-oxazolidinone 在 咪唑 、 正丁基锂 、 三氟化硼乙醚 、 caesium carbonate 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 生成 (3S,4S)-methyl 3-hydroxy-6-methyl-4-t-butoxycarbonylamino-heptanoate
  参考文献：
  名称：

  Lewis acid-promoted direct substitution of 4-methoxy- and 4-phenylthio-2-oxazolidinones by alkyl cuprates. Facile preparation of (3s,4s)-statine and (3s,4s)-cyclohexylstatine.

  摘要：

  Treatment of 4-methoxy- and 4-phenylthio-2-oxazolidinones with a combination of cuprates and BF3 results in smooth formation of 4-alkyl and 4-aryl derivatives in high yield. By this method, the titled compounds of biological interest are readily synthesized from (4S,5S)-5-allyl-4-methoxy (or 4-phenylthio)-2-oxazolidinones stereoselectively.

  DOI：

  10.1016/0040-4039(91)80822-n
• 作为产物：
  描述：

  在 lithium di(n-butyl)cuprate 作用下， 生成 (4S,5S)-5-allyl-4-methoxy-2-oxazolidinone
  参考文献：
  名称：

  Versatile chiral synthons for vic-amino alcohols. Facile synthesis of (2S,3R)-3-hydroxyglutamic acid and (+)-statine

  摘要：

  DOI：

  10.1021/jo00249a055

文献信息

• Chiral synthons for 2-amino alcohols. Facile preparation of optically active amino hydroxy acids of biological interest.
  作者：Tadao Ishizuka、Seigo Ishibuchi、Takehisa Kunieda

  DOI：10.1016/s0040-4020(01)80540-8

  日期：1993.2

  promising method for the versatile synthesis of chiral 2-amino alcohols is provided by the enantioselective functionalization of the olefinic moiety of the simple heterocycle, 2-oxazolone, involving a stereodefined introduction of easily replaceable groups followed by stepwise substitution. Versatility of this method is shown in chiral synthesis of unusual hydroxy amino acids such as statine and hydroxyglutamic

  通过简单杂环2-恶唑酮的烯烃部分的对映选择性官能化，涉及立体定义的易替换基团的引入，然后逐步取代，为手性2-氨基醇的通用合成提供了一种有前途的方法。这种方法的多功能性在不寻常的羟基氨基酸（例如他汀和羟基谷氨酸）的手性合成中得到了证明，它们是生物活性肽的关键成分。
• New camphor-derived auxiliaries in methoxyselenylation and methoxybromination with opposite diastereofacial selectivity
  作者：Tadao Ishizuka、Seigo Ishibuchi、Takehisa Kunieda

  DOI：10.1016/s0040-4039(00)99269-4

  日期：1989.1

  Methoxyselenylation and methoxybromination of chiral 3-acyl-2-oxazolones with PhSeCl/MeOH and Br2/MeC(OMe)3 smoothly proceed to result in highly stereoselective formation of chiral synthons for β-amino alcohols, but with opposite π-facial selectivity.

  用PhSeCl / MeOH和Br 2 / MeC（OMe）3进行手性3-酰基-2-恶唑酮的甲氧基硒基化和甲氧基溴化反应平稳进行，导致β-氨基醇的手性合成子高度立体选择性形成，但π面选择性相反。
• Ishizuka, Tadao; Morooka, Kohei; Ishibuchi, Seigo, Heterocycles, 1996, vol. 42, # 2, p. 837 - 848
  作者：Ishizuka, Tadao、Morooka, Kohei、Ishibuchi, Seigo、Kunieda, Takehisa

  DOI：——

  日期：——
• Kouyama, Takafumi; Matsunaga, Hirofumi; Ishizuka, Tadao, Heterocycles, 1997, vol. 44, # 1, p. 479 - 486
  作者：Kouyama, Takafumi、Matsunaga, Hirofumi、Ishizuka, Tadao、Kunieda, Takehisa

  DOI：——

  日期：——
• Lewis acid-promoted direct substitution of 4-methoxy- and 4-phenylthio-2-oxazolidinones by alkyl cuprates. Facile preparation of (3s,4s)-statine and (3s,4s)-cyclohexylstatine.
  作者：Seigo Ishibuchi、Yumi Ikematsu、Tadao Ishizuka、Takehisa Kunieda

  DOI：10.1016/0040-4039(91)80822-n

  日期：1991.7

  Treatment of 4-methoxy- and 4-phenylthio-2-oxazolidinones with a combination of cuprates and BF3 results in smooth formation of 4-alkyl and 4-aryl derivatives in high yield. By this method, the titled compounds of biological interest are readily synthesized from (4S,5S)-5-allyl-4-methoxy (or 4-phenylthio)-2-oxazolidinones stereoselectively.