(4bR,6R,8aR)-1,3,6,9,9-Pentamethyl-1,4b,5,6,7,8,8a,9-octahydro-10-oxa-1,3-diaza-phenanthrene-2,4-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃嘧啶类
• 英文名称: (4bR,6R,8aR)-1,3,6,9,9-Pentamethyl-1,4b,5,6,7,8,8a,9-octahydro-10-oxa-1,3-diaza-phenanthrene-2,4-dione
• 英文别名: (6aR,9R,10aR)-2,4,6,6,9-pentamethyl-6a,7,8,9,10,10a-hexahydroisochromeno[3,4-d]pyrimidine-1,3-dione
• 化学式: C₁₆H₂₄N₂O₃
• 分子量: 292.378
• InChiKey: JTDKVDHTJCNREV-GMTAPVOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4bR,6R,8aR)-1,3,6,9,9-Pentamethyl-1,4b,5,6,7,8,8a,9-octahydro-10-oxa-1,3-diaza-phenanthrene-2,4-dione 在 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 以93%的产率得到(6aRS,9RS,10aRS)-(+/-)-3,4,6,6a,7,8,9,10,10a-nonahydro-2,4,6,6,9-pentamethyl-[2]benzopyrano[3,4-d]pyrimidine-1(2H)-one
  参考文献：
  名称：

  Regioselective Reduction and Ring Cleavage of Polycyclic Barbituric Acid Analogues Derived from Intramolecular Hetero-Diels−Alder Reactions

  摘要：

  DOI：

  10.1002/1099-0690(200105)2001:9<1625::aid-ejoc1625>3.3.co;2-5
• 作为产物：
  描述：

  (+)-香茅醛 、 1,3-二甲基巴比妥酸 在 ethylenediamine Tetraacetic Acid 作用下， 反应 0.08h， 以97%的产率得到(4bR,6R,8aR)-1,3,6,9,9-Pentamethyl-1,4b,5,6,7,8,8a,9-octahydro-10-oxa-1,3-diaza-phenanthrene-2,4-dione
  参考文献：
  名称：

  通过立体控制的分子内环加成反应合成对映体二氢吡喃

  摘要：

  环状1、3-二羧酸衍生物（1），（2）和（3）与（R）-或（S）-香茅醛（4/5）反应，得到对映体三环二氢吡喃（10），（11） ，（12）和（13），可能是通过100％立体控制的分子内环加成反应。

  DOI：

  10.1016/0040-4039(81)80059-7

文献信息

• Intra- and intermolecular hetero-Diels-Alder reactions. 45. Simple and induced diastereoselectivity in intramolecular hetero-Diels-Alder reactions of 1-oxa-1,3-butadienes. Experimental data and calculations
  作者：Lutz F. Tietze、Holger Geissler、Jens Fennen、Thomas Brumby、Siegbert Brand、Gerhard Schulz

  DOI：10.1021/jo00080a030

  日期：1994.1

  The simple and induced diastereoselectivity of the intramolecular hetero-Diels-Alder reaction of the alkylidene 1,3-dicarbonyl compounds 7a-e, obtained in situ by Knoevenagel condensation of the aldehydes 5a-e and dimethylbarbituric acid 6, was investigated experimentally and theoretically. In all examples the selectivity is very high; thus the domino reaction of 5a and 6 gives nearly exclusively the trans-fused tricyclic dihydropyran 8 (trans/cis = 98.8:1.2). In the similar reactions of the chiral aldehydes 5b-e and 6 the trans-cycloadducts 28, 33, 36, and 41 are the main products out of four possible diastereomers. The induced diastereoselectivity for the reaction of 5b and 5e with 6 is >99:1 and for the reaction of 5e and Sd-with 6, 95.2:3.6 and 94.1:4.7, respectively. Semiempirical AM1 calculations have been used to locate the transition structures of the intramolecular hetero-Diels-Alder reaction of 7a. The results were employed to create new parameters for the MM2-type force-field to determine the transition structures of 7b-e. The obtained data were compared with the experimental results of the cycloadditions and showed an excellent agreement.
• Towards automated structureelucidation
  作者：W. Offermann、W. Kuhn、J. Stelten、D. Leibfritz、G.v. Kiedrowski、L.F. Tietze

  DOI：10.1016/s0040-4020(01)90601-5

  日期：1986.1
• TIETZE, LUTZ F.;BRAND, SIEGBERT;BRUMBY, THOMAS;FENNEN, JENS, ANGEW. CHEM., 102,(1990) N, C. 675-677
  作者：TIETZE, LUTZ F.、BRAND, SIEGBERT、BRUMBY, THOMAS、FENNEN, JENS

  DOI：——

  日期：——