methyl 15-methoxy-ent-halima-1(10),13E-dien-18-oate | 412913-70-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 15-methoxy-ent-halima-1(10),13E-dien-18-oate
• 英文别名: methyl (1S,5S,6R,8aS)-5-[(E)-5-methoxy-3-methylpent-3-enyl]-1,5,6-trimethyl-2,3,6,7,8,8a-hexahydronaphthalene-1-carboxylate
• CAS: 412913-70-3
• 化学式: C₂₂H₃₆O₃
• 分子量: 348.526
• InChiKey: VOAZGCHWYXHTNJ-CZCIYWNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 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-ent-halima-1(10),13E-dien-18-oate 在 吡啶 、 sodium hydroxide 、 氯化亚砜 、 silver(l) oxide 作用下， 以 甲醇 、 乙醚 、 苯 为溶剂， 反应 13.0h， 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
• 作为产物：
  描述：

  ent-halimic acid methyl ester 、 碘甲烷 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.17h， 以92%的产率得到methyl 15-methoxy-ent-halima-1(10),13E-dien-18-oate
  参考文献：
  名称：

  Synthesis ofent-Halimanolides froment-Halimic Acid

  摘要：

  我们从恩特-卤代甲酸中合成了三种天然恩特-卤代甲醇。它们的结构已得到确认，绝对构型也已确定。丁烯内酯的合成采用了贝斯特曼方法，δ-羟基丁烯内酯的合成采用了布库瓦拉斯方法。

  DOI：

  10.1055/s-2005-918475

文献信息

• Synthesis of<i>ent</i>-Halimanolides from<i>ent</i>-Halimic Acid
  作者：I. S. Marcos、A. B. Pedrero、M. J. Sexmero、D. Diez、N. García、M. A. Escola、P. Basabe、A. Conde、R. F. Moro、J. G. Urones

  DOI：10.1055/s-2005-918475

  日期：——

  Three natural ent-halimanolides have been synthesized from ent-halimic acid. Their structures have been confirmed as well as their absolute configurations established. Bestmann methodology has been used for the synthesis of butenolides and for the synthesis of γ-hydroxybutenolides the Boukouvalas method has been employed.

  我们从恩特-卤代甲酸中合成了三种天然恩特-卤代甲醇。它们的结构已得到确认，绝对构型也已确定。丁烯内酯的合成采用了贝斯特曼方法，δ-羟基丁烯内酯的合成采用了布库瓦拉斯方法。
• Synthesis and absolute configuration of three natural ent-halimanolides with biological activity
  作者：I.S Marcos、A.B Pedrero、M.J Sexmero、D Diez、P Basabe、F.A Hernández、J.G Urones

  DOI：10.1016/s0040-4039(02)02535-2

  日期：2003.1

  now have been synthesized from ent-halimic acid. Their structure have been confirmed as well as their absolute configurations established. Bestmann methodology has been used for the synthesis of butenolides and for the γ-hydroxybutenolides synthesis the Boukouvalas method has been employed. Biological testing has been carried out on these compounds.

  迄今已知的前三种天然对羟基卤化物是由对卤代酸合成的。已经确认了它们的结构以及确定的绝对构型。Bestmann方法已用于丁烯内酯的合成，而γ-羟基丁烯内酯的合成已使用Boukouvalas方法。已经对这些化合物进行了生物测试。
• Synthesis and Absolute Configuration of the Supposed Structure of Cladocoran A and B
  作者：I. S. Marcos、A. B. Pedrero、M. J. Sexmero、D. Diez、P. Basabe、F. A. Hernández、H. B. Broughton、J. G. Urones

  DOI：10.1055/s-2002-19318

  日期：——

  The proposed structures of cladocoran A and B, sesterterpenoid y-hydroxybutenolides, were synthesized from ent-halimic acid.

  cladocoran A 和 B 的拟议结构，sesterterpenoid y-羟基丁烯内酯，是从 ent-halimic 酸合成的。
• Synthesis of novel antitumoural analogues of dysidiolide from ent-halimic acid
  作者：I.S. Marcos、M.A. Escola、R.F. Moro、P. Basabe、D. Diez、F. Sanz、F. Mollinedo、J. de la Iglesia-Vicente、B.G. Sierra、J.G. Urones

  DOI：10.1016/j.bmc.2007.06.007

  日期：2007.9.1

  Several sesterterpenolides analogues of dysidiolide have been synthesized and their in vitro antitumoural activity against human HeLa, A549, HT-29 and HL-60 carcinoma cells is presented. The proliferation inhibition data showed a significant antitumour activity of the compounds 1b, 2a, 2b, 3a, 3b, 4a, 4b, 5, inhibiting proliferation of distinct cancer cell types with an IC50 in the low micromolar range. (c) 2007 Elsevier Ltd. All rights reserved.
• 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.