methyl (2Z)-2-[(3'aS,7'aS)-7'a-methylspiro[1,3-dioxolane-2,5'-2,3,3a,4,6,7-hexahydroindene]-1'-ylidene]propanoate | 1044141-03-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (2Z)-2-[(3'aS,7'aS)-7'a-methylspiro[1,3-dioxolane-2,5'-2,3,3a,4,6,7-hexahydroindene]-1'-ylidene]propanoate
• CAS: 1044141-03-8
• 化学式: C₁₆H₂₄O₄
• 分子量: 280.364
• InChiKey: HMFBIMJZTYADBG-AYTLTXPASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (2Z)-2-[(3'aS,7'aS)-7'a-methylspiro[1,3-dioxolane-2,5'-2,3,3a,4,6,7-hexahydroindene]-1'-ylidene]propanoate 在 selenium(IV) oxide 作用下， 以 1,4-二氧六环 为溶剂， 以56%的产率得到
  参考文献：
  名称：

  Synthesis of BC-ring model of globostellatic acid X methyl ester, an anti-angiogenic substance from marine sponge

  摘要：

  Concise synthesis of BC-ring model compounds of 13E, 17E-globostellatic acid X methyl ester, an anti-angiogenic triterpene derivative from Indonesian marine sponge, was achieved through ynolate olefination and allylic oxidation as key steps. The model compound 5, which was synthesized within 10 reaction steps from commercially available Hajos-Parrish ketone, showed anti-proliferative activity against HUVECs with moderate selectivity. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.05.018
• 作为产物：
  描述：

  ethyl 2,2-dibromopropanoate 、 (3a'S,7a'S)-7a'-methylhexahydrospiro[[1,3]dioxolane-2,5'-inden]-1'(6'H)-one 、 碘甲烷 在 叔丁基锂 、 六甲基磷酰三胺 作用下， 以48%的产率得到methyl (2Z)-2-[(3'aS,7'aS)-7'a-methylspiro[1,3-dioxolane-2,5'-2,3,3a,4,6,7-hexahydroindene]-1'-ylidene]propanoate
  参考文献：
  名称：

  Synthesis of BC-ring model of globostellatic acid X methyl ester, an anti-angiogenic substance from marine sponge

  摘要：

  Concise synthesis of BC-ring model compounds of 13E, 17E-globostellatic acid X methyl ester, an anti-angiogenic triterpene derivative from Indonesian marine sponge, was achieved through ynolate olefination and allylic oxidation as key steps. The model compound 5, which was synthesized within 10 reaction steps from commercially available Hajos-Parrish ketone, showed anti-proliferative activity against HUVECs with moderate selectivity. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.05.018

文献信息

• Synthesis of BC-ring model of globostellatic acid X methyl ester, an anti-angiogenic substance from marine sponge
  作者：Naoyuki Kotoku、Nao Tamada、Asami Hayashi、Motomasa Kobayashi

  DOI：10.1016/j.bmcl.2008.05.018

  日期：2008.6

  Concise synthesis of BC-ring model compounds of 13E, 17E-globostellatic acid X methyl ester, an anti-angiogenic triterpene derivative from Indonesian marine sponge, was achieved through ynolate olefination and allylic oxidation as key steps. The model compound 5, which was synthesized within 10 reaction steps from commercially available Hajos-Parrish ketone, showed anti-proliferative activity against HUVECs with moderate selectivity. (C) 2008 Elsevier Ltd. All rights reserved.