(-)-(R,R)-3-hydroxy-2H-pyrrolo[2,3-b]indolo[5,5a,6-b,a]quinazoline-9-(8H)-7'-dione | 1380540-71-5

• 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: (-)-(R,R)-3-hydroxy-2H-pyrrolo[2,3-b]indolo[5,5a,6-b,a]quinazoline-9-(8H)-7'-dione
• 英文别名: (R, R)-cruciferane；(-)-(2R,3R)-3-hydroxy-2H-pyrrolo[2,3-b]indolo[5,5a,6-b,a]quinazoline-9(8H),7'-dione；(8R,19R)-8-hydroxy-1,11-diazapentacyclo[9.7.1.02,7.08,19.012,17]nonadeca-2,4,6,12,14,16-hexaene-10,18-dione
• CAS: 1380540-71-5
• 化学式: C₁₇H₁₂N₂O₃
• 分子量: 292.294
• InChiKey: DMWBWCODLSCGLM-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  60.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  色胺酮 在 sodium tetrahydroborate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 为溶剂， 反应 6.75h， 生成 (-)-(R,R)-3-hydroxy-2H-pyrrolo[2,3-b]indolo[5,5a,6-b,a]quinazoline-9-(8H)-7'-dione
  参考文献：
  名称：

  Aryne Insertion Reactions Leading to Bioactive Fused Quinazolinones: Diastereoselective Total Synthesis of Cruciferane

  摘要：

  Insertion reactions of an in situ generated arynes to a variety of suitably substituted 1,3-quinazolin-4-ones have been demonstrated for a new efficient one-step approach to a diverse range of fused quinazolinone architectures. The present protocol has been effectively utilized to accomplish the concise total synthesis of recently isolated bioactive natural products tryptanthrin, phaitanthrins A-C, and cruciferane.

  DOI：

  10.1021/ol4018062

文献信息

• Direct Catalytic Asymmetric Synthesis of β-Hydroxy Acids from Malonic Acid
  作者：Hang Gao、Zhenli Luo、Pingjin Ge、Junqian He、Feng Zhou、Peipei Zheng、Jun Jiang

  DOI：10.1021/acs.orglett.5b02891

  日期：2015.12.18

  A nickel(II) catalyzed asymmetric synthesis of β-hydroxy acids from malonic acid and ketones was developed, revealing for the first time the synthetic utility of malonic acid in the construction of chiral carboxyl acids; importantly, the synthetic potential of this strategy was further demonstrated by the rapid construction of cephalanthrin A, phaitanthrin B, cruciferane, and rice metabolites.

  开发了镍（II）催化由丙二酸和酮不对称合成β-羟基酸的方法，这首次揭示了丙二酸在手性羧酸的合成中的合成作用。重要的是，该方法的合成潜力通过快速构建头孢菌素A，紫杉醇B，十字花青素和大米代谢产物得到了进一步证明。
• Aryne Insertion Reactions Leading to Bioactive Fused Quinazolinones: Diastereoselective Total Synthesis of Cruciferane
  作者：Sagar D. Vaidya、Narshinha P. Argade

  DOI：10.1021/ol4018062

  日期：2013.8.2

  Insertion reactions of an in situ generated arynes to a variety of suitably substituted 1,3-quinazolin-4-ones have been demonstrated for a new efficient one-step approach to a diverse range of fused quinazolinone architectures. The present protocol has been effectively utilized to accomplish the concise total synthesis of recently isolated bioactive natural products tryptanthrin, phaitanthrins A-C, and cruciferane.