(1R)-4-methyl-1-(5,7,12,14-tetraoxatetracyclo[6.6.2.04,16.011,15]hexadeca-1,3,8(16),9,11(15)-pentaen-2-yl)pent-3-en-1-ol | 206996-08-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1R)-4-methyl-1-(5,7,12,14-tetraoxatetracyclo[6.6.2.04,16.011,15]hexadeca-1,3,8(16),9,11(15)-pentaen-2-yl)pent-3-en-1-ol
• CAS: 206996-08-9
• 化学式: C₁₈H₁₈O₅
• 分子量: 314.338
• InChiKey: XSIRTOGAWWKRSQ-GFCCVEGCSA-N

物化性质

• 沸点：
  535.1±50.0 °C(Predicted)
• 密度：
  1.329±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R)-4-methyl-1-(5,7,12,14-tetraoxatetracyclo[6.6.2.04,16.011,15]hexadeca-1,3,8(16),9,11(15)-pentaen-2-yl)pent-3-en-1-ol 在 lithium perchlorate 作用下， 以 水 、 乙腈 为溶剂， 生成 紫草素
  参考文献：
  名称：

  Concise and Efficient Total Syntheses of Alkannin and Shikonin

  摘要：

  Two enantiomic natural products with wound-healing properties, alkannin (1) and shikonin (2), are accessible by a short and efficient total synthesis. The success was achieved by a novel protecting system for masking of 5,8-dihydroxy-1,4-naphthoquinones (naphthazarins) and a highly stereoselective ketone reduction.

  DOI：

  10.1002/(sici)1521-3773(19980403)37:6<839::aid-anie839>3.0.co;2-j
• 作为产物：
  描述：

  4-溴-萘并[1,8-DE:4,5-D’E’]BIS[1,3]二氧(杂)芑 在 叔丁基锂 、 乙醛 、 (-)-diisopinocamphenylborane chloride 作用下， 以 四氢呋喃 为溶剂， 反应 17.5h， 生成 (1R)-4-methyl-1-(5,7,12,14-tetraoxatetracyclo[6.6.2.04,16.011,15]hexadeca-1,3,8(16),9,11(15)-pentaen-2-yl)pent-3-en-1-ol
  参考文献：
  名称：

  Concise and Efficient Total Syntheses of Alkannin and Shikonin

  摘要：

  Two enantiomic natural products with wound-healing properties, alkannin (1) and shikonin (2), are accessible by a short and efficient total synthesis. The success was achieved by a novel protecting system for masking of 5,8-dihydroxy-1,4-naphthoquinones (naphthazarins) and a highly stereoselective ketone reduction.

  DOI：

  10.1002/(sici)1521-3773(19980403)37:6<839::aid-anie839>3.0.co;2-j

文献信息

• Synthesis and antitumour activity of β-hydroxyisovalerylshikonin analogues
  作者：Zhen Rao、Xin Liu、Wen Zhou、Jing Yi、Shao-Shun Li

  DOI：10.1016/j.ejmech.2011.05.065

  日期：2011.9

  β-hydroxyisovalerylshikonin analogues bearing oxygen-containing substituents at the side-chain hydroxyl of shikonin were designed and synthesized. The cytotoxicities of these compounds were evaluated in vitro against multi-drug resistant (MDR) cell lines DU-145 and HeLa. Most compounds exhibited significant inhibitory activity on both cell lines. The structure–activity relationship showed the analogues with ether substituents

  设计并合成了一系列新型的β-羟基异戊基紫草素类似物，这些类似物在紫草素的侧链羟基上带有含氧取代基。在体外评估了这些化合物对多药耐药（MDR）细胞DU-145和HeLa的细胞毒性。大多数化合物对两种细胞系均显示出显着的抑制活性。构效关系表明，带有醚取代基的类似物对DU-145表现出最强的抗肿瘤活性和选择性细胞毒性。在具有醚取代基的化合物中，增加带有β-羟基的碳中的空间位阻或用乙酰氧基或甲氧基代替β-羟基会导致细胞毒性下降。
• Concise and Efficient Total Syntheses of Alkannin and Shikonin
  作者：K. C. Nicolaou、David Hepworth

  DOI：10.1002/(sici)1521-3773(19980403)37:6<839::aid-anie839>3.0.co;2-j

  日期：1998.4.3

  Two enantiomic natural products with wound-healing properties, alkannin (1) and shikonin (2), are accessible by a short and efficient total synthesis. The success was achieved by a novel protecting system for masking of 5,8-dihydroxy-1,4-naphthoquinones (naphthazarins) and a highly stereoselective ketone reduction.