(-)-norbalasubramide | 1201890-55-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (-)-norbalasubramide
• 英文别名: (5R,6S)-norbalasubramide；(5R,6S)-5-hydroxy-6-phenyl-1,2,3,5,6,7-hexahydroazocino[5,4-b]indol-4-one
• CAS: 1201890-55-2
• 化学式: C₁₉H₁₈N₂O₂
• 分子量: 306.364
• InChiKey: BNHSSLGGGYRMIX-FUHWJXTLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  65.1
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-(2-溴乙基)吲哚 在 4-二甲氨基吡啶 、 sodium dihydrogenphosphate dihydrate 、 四丁基氟化铵 、 氨 、 lithium 、 copper(II) bis(trifluoromethanesulfonate) 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 、 叔丁醇 为溶剂， 反应 22.75h， 生成 (-)-norbalasubramide
  参考文献：
  名称：

  The Use of Sodium Chlorite in the Direct Synthesis of Glycidic Amides: Enantiopure Synthesis of Both Enantiomers of Norbalasubramide

  摘要：

  Recently, the first direct method for preparing 2,3-epoxyamides (glycidic amides) was disclosed. Now in this letter, the enantiopure synthesis of both enantiomers of norbalasubramide featuring this synthetic method is reported. To this end, chiral N-allyltryptamine 12 was prepared and transformed into an inseparable mixture of diastereomeric epoxyamides 13a/13b, which were submitted to intramolecular cyclization with Cu(OTf)(2) to afford a separable mixture of eight-membered ring lactams 14a and 14b. Finally, after removal of the protective group and the chiral auxiliary an enantiopure synthesis of the title compounds was completed.

  DOI：

  10.1055/s-0032-1316893

文献信息

• Highly Efficient Asymmetric Epoxidation of Electron-Deficient α,β-Enones and Related Applications to Organic Synthesis
  作者：Changwu Zheng、Yawen Li、Yingquan Yang、Haifeng Wang、Haifeng Cui、Junkang Zhang、Gang Zhao

  DOI：10.1002/adsc.200900041

  日期：2009.7

  The asymmetric epoxidation of electron‐deficient olefins has been achieved using inexpensive and readily available prolinols as catalysts with good to excellent yields and enantioselectivities. The utility of the resulting chiral epoxides was illustrated by elaboration to several synthetically useful compounds featuring a concise synthesis of (−)‐(5R,6S)‐balasubramide.

  使用价格低廉，易于获得的脯氨醇作为催化剂，可以实现电子不足的烯烃的不对称环氧化，其收率和对映选择性都非常好。详细阐述了几种合成有用的化合物，这些化合物以（-）-（5 R，6 S）-巴拉苏酰胺的简明合成为例，说明了所得手性环氧化物的实用性。
• The Use of Sodium Chlorite in the Direct Synthesis of Glycidic Amides: Enantiopure Synthesis of Both Enantiomers of Norbalasubramide
  作者：Leticia Quintero、Fernando Sartillo-Piscil、Lilia Fuentes、Mireya Hernández-Juarez、Joel Terán

  DOI：10.1055/s-0032-1316893

  日期：——

  Recently, the first direct method for preparing 2,3-epoxyamides (glycidic amides) was disclosed. Now in this letter, the enantiopure synthesis of both enantiomers of norbalasubramide featuring this synthetic method is reported. To this end, chiral N-allyltryptamine 12 was prepared and transformed into an inseparable mixture of diastereomeric epoxyamides 13a/13b, which were submitted to intramolecular cyclization with Cu(OTf)(2) to afford a separable mixture of eight-membered ring lactams 14a and 14b. Finally, after removal of the protective group and the chiral auxiliary an enantiopure synthesis of the title compounds was completed.