methyl 15-methoxy-18a-homo-1(10),13E-ent-halimadien-18-oate | 613680-64-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 15-methoxy-18a-homo-1(10),13E-ent-halimadien-18-oate
• 英文别名: methyl 2-[(1R,5S,6R,8aR)-5-[(E)-5-methoxy-3-methylpent-3-enyl]-1,5,6-trimethyl-2,3,6,7,8,8a-hexahydronaphthalen-1-yl]acetate
• CAS: 613680-64-1
• 化学式: C₂₃H₃₈O₃
• 分子量: 362.553
• InChiKey: ZYLGLRRCAPQUTG-NQSCQDFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 15-methoxy-18a-homo-1(10),13E-ent-halimadien-18-oate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 0.75h， 以92%的产率得到15-methoxy-18a-homo-1(10),13E-ent-halimadien-18-ol
  参考文献：
  名称：

  Synthesis of Bioactive Sesterterpenolides from ent-Halimic Acid. 15-Epi-ent-cladocoran A and B

  摘要：

  The bioactive sesterterpenoid gamma-hydroxybutenolides 15,18-bisepi-ent-Cladocoran A and B, 1 and 2, and 15-epi-ent-Cladocoran A and B, 57 and 55, were synthesized from ent-halimic acid. The synthesized sesterterpenolids 2, 55, 57, and 59 inhibited cellular proliferation (IC50 congruent to 2 muM) of a number of human leukaemic and solid tumor cell lines.

  DOI：

  10.1021/jo034663l
• 作为产物：
  描述：

  15-methoxy-1(10),13E-ent-halimadien-18-oyl chloride 在 silver(l) oxide 作用下， 以 乙醚 为溶剂， 反应 9.0h， 生成 methyl 15-methoxy-18a-homo-1(10),13E-ent-halimadien-18-oate
  参考文献：
  名称：

  Synthesis of Bioactive Sesterterpenolides from ent-Halimic Acid. 15-Epi-ent-cladocoran A and B

  摘要：

  The bioactive sesterterpenoid gamma-hydroxybutenolides 15,18-bisepi-ent-Cladocoran A and B, 1 and 2, and 15-epi-ent-Cladocoran A and B, 57 and 55, were synthesized from ent-halimic acid. The synthesized sesterterpenolids 2, 55, 57, and 59 inhibited cellular proliferation (IC50 congruent to 2 muM) of a number of human leukaemic and solid tumor cell lines.

  DOI：

  10.1021/jo034663l

文献信息

• Synthesis of Bioactive Sesterterpenolides from <i>e</i><i>nt</i>-Halimic Acid. 15-Epi-<i>e</i><i>nt</i>-cladocoran A and B
  作者：I. S. Marcos、A. B. Pedrero、M. J. Sexmero、D. Diez、P. Basabe、N. García、R. F. Moro、H. B. Broughton、F. Mollinedo、J. G. Urones

  DOI：10.1021/jo034663l

  日期：2003.9.1

  The bioactive sesterterpenoid gamma-hydroxybutenolides 15,18-bisepi-ent-Cladocoran A and B, 1 and 2, and 15-epi-ent-Cladocoran A and B, 57 and 55, were synthesized from ent-halimic acid. The synthesized sesterterpenolids 2, 55, 57, and 59 inhibited cellular proliferation (IC50 congruent to 2 muM) of a number of human leukaemic and solid tumor cell lines.