(4R,5S,6S)-5-(4-Methoxy-benzyloxy)-4-(4-methoxy-phenoxymethyl)-2-methyl-6-vinyl-5,6-dihydro-4H-[1,3]oxazine | 787632-44-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4R,5S,6S)-5-(4-Methoxy-benzyloxy)-4-(4-methoxy-phenoxymethyl)-2-methyl-6-vinyl-5,6-dihydro-4H-[1,3]oxazine
• 英文别名: (4R,5S,6S)-6-ethenyl-4-[(4-methoxyphenoxy)methyl]-5-[(4-methoxyphenyl)methoxy]-2-methyl-5,6-dihydro-4H-1,3-oxazine
• CAS: 787632-44-4
• 化学式: C₂₃H₂₇NO₅
• 分子量: 397.471
• InChiKey: QWYROSRLTOLDLU-VJBWXMMDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  58.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4R,5S,6S)-5-(4-Methoxy-benzyloxy)-4-(4-methoxy-phenoxymethyl)-2-methyl-6-vinyl-5,6-dihydro-4H-[1,3]oxazine 在 ammonium cerium(IV) nitrate 作用下， 以 乙醚 、 水 、 乙腈 为溶剂， 反应 2.0h， 生成 D-threo-N-acetyl-sphingosine
  参考文献：
  名称：

  通过乙烯基恶嗪与格氏试剂的铜介导的S（N）2'反应立体选择性合成反式烯烃。D-苏式-鞘氨醇的不对称合成。

  摘要：

  研究了在CuCN存在下6-乙烯基-5,6-二氢-4H- [1,3]恶嗪与Grignard试剂的S（N）2'反应，并观察到形成双键的高反选择性与各种RMgX。S（N）2'反应，与区域选择性不对称氨基羟基化反应相结合，为D-苏-N-乙酰基鞘氨醇的不对称合成提供了一条高效途径。

  DOI：

  10.1016/j.tetlet.2007.01.145
• 作为产物：
  描述：

  ethyl (2E)-4-(4-methoxyphenoxy)but-2-enoate 在 lithium hydroxide 、 potassium osmate(VI) 、 sodium hydride 、 二异丁基氢化铝 、 甲基磺酰氯 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 10.5h， 生成 (4R,5S,6S)-5-(4-Methoxy-benzyloxy)-4-(4-methoxy-phenoxymethyl)-2-methyl-6-vinyl-5,6-dihydro-4H-[1,3]oxazine
  参考文献：
  名称：

  Oxazine formation by MsCl/Et3N as a convenient tool for the stereochemical interconversion of the hydroxyl group in N-acetyl 1,3-aminoalcohols. Asymmetric synthesis of N-acetyl l-xylo- and l-arabino-phytosphingosines

  摘要：

  Use of MsCl/Et3N was proven to provide a convenient synthetic tool for the stereochemical intercoversion of the hydroxyl group in N-acetyl 1,3-aminoalcohols. Thus, under these conditions, the alcohols 4 and 6 smoothly converted to the oxazines 5 and 7, respectively, which were hydrolyzed to generate the corresponding inverted alcohols 6 and 4 in one pot. Further elaboration of 4 and 6 led to the efficient asymmetric synthesis of N-acetyl L-xylo- and L-arabino-phytosphingosines (11 and 15), respectively, via olefin cross metathesis reactions. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2004.08.030

文献信息

• Oxazine formation by MsCl/Et3N as a convenient tool for the stereochemical interconversion of the hydroxyl group in N-acetyl 1,3-aminoalcohols. Asymmetric synthesis of N-acetyl l-xylo- and l-arabino-phytosphingosines
  作者：Om V. Singh、Dorothy J. Kampf、Hyunsoo Han

  DOI：10.1016/j.tetlet.2004.08.030

  日期：2004.9

  Use of MsCl/Et3N was proven to provide a convenient synthetic tool for the stereochemical intercoversion of the hydroxyl group in N-acetyl 1,3-aminoalcohols. Thus, under these conditions, the alcohols 4 and 6 smoothly converted to the oxazines 5 and 7, respectively, which were hydrolyzed to generate the corresponding inverted alcohols 6 and 4 in one pot. Further elaboration of 4 and 6 led to the efficient asymmetric synthesis of N-acetyl L-xylo- and L-arabino-phytosphingosines (11 and 15), respectively, via olefin cross metathesis reactions. (C) 2004 Published by Elsevier Ltd.
• Stereoselective synthesis of trans-olefins by the copper-mediated SN2′ reaction of vinyl oxazines with Grignard reagents. Asymmetric synthesis of d-threo-sphingosines
  作者：Om V. Singh、Hyunsoo Han

  DOI：10.1016/j.tetlet.2007.01.145

  日期：2007.3

  The S(N)2' reaction of 6-vinyl-5,6-dihydro-4H-[1,3]oxazines with Grignard reagents in the presence of CuCN was studied, and high trans selectivity for the formation of double bond was observed with a variety of RMgX. The S(N)2' reaction, coupled with regioselective asymmetric aminohydroxylation reaction, provided a highly efficient route for the asymmetric synthesis of D-threo-N-acetylsphingosine.

  研究了在CuCN存在下6-乙烯基-5,6-二氢-4H- [1,3]恶嗪与Grignard试剂的S（N）2'反应，并观察到形成双键的高反选择性与各种RMgX。S（N）2'反应，与区域选择性不对称氨基羟基化反应相结合，为D-苏-N-乙酰基鞘氨醇的不对称合成提供了一条高效途径。