19-methyl hydrogen 13,14,15,16-tetranorlabd-8(17)-ene-12,19-dioate | 39668-48-9

• 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: 19-methyl hydrogen 13,14,15,16-tetranorlabd-8(17)-ene-12,19-dioate
• 英文别名: methyl 12-hydroxy-12-oxo-13,14,15,16-tetranorlabd-8(17)-en-19-oate；2-((1S,4aR,5S,8aR)-5-(methoxycarbonyl)-5,8a-di-methyl-2-methylenedecahydronaphthalen-1-yl)acetic acid；2-[(1S,4aR,5S,8aR)-5-methoxycarbonyl-5,8a-dimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalen-1-yl]acetic acid
• CAS: 39668-48-9
• 化学式: C₁₇H₂₆O₄
• 分子量: 294.391
• InChiKey: OTVMAFZZQQYPPO-IXKJSCDLSA-N

物化性质

• 熔点：
  127-128 °C(Solvent: Methanol)
• 沸点：
  401.6±38.0 °C(predicted)
• 密度：
  1.10±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  19-methyl hydrogen 13,14,15,16-tetranorlabd-8(17)-ene-12,19-dioate 在 对甲苯磺酸 、 间氯过氧苯甲酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 乙醚 、 二氯甲烷 、 苯 为溶剂， 反应 18.0h， 生成 (4bS,8S,8aR)-4b,8-Dimethyl-3-oxo-3,4b,5,6,7,8,8a,9-octahydro-1H-2-oxa-phenanthrene-8-carboxylic acid methyl ester
  参考文献：
  名称：

  Enantiospecific syntheses of the potent bioactives nagilactone F and the mould metabolite LL-Z1271α an evaluation of their allelopathic potential

  摘要：

  Improved syntheses are described for nagilactone F and the antibiotic LL-Z1271 alpha, two of the most potent bioactive members of the podolactone family. The allelopathic potential of some members of this podolactone series has been evaluated, with the result that the metabolite LL-Z1271 alpha is one of the most active compounds. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00355-5
• 作为产物：
  描述：

  dimethyl 8-oxo-13,14,15,16,17-pentanorlabdane-12,19-dioate 在 氢氧化钾 、 四氯化钛 、 锌 作用下， 反应 17.17h， 生成 19-methyl hydrogen 13,14,15,16-tetranorlabd-8(17)-ene-12,19-dioate
  参考文献：
  名称：

  Cambie, Richard C.; McNally, Heather M.; Robertson, John D., Australian Journal of Chemistry, 1984, vol. 37, # 2, p. 409 - 416

  摘要：

  DOI：

文献信息

• First Enantiospecific Syntheses of Marine Merosesquiterpenes Neopetrosiquinones A and B: Evaluation of Biological Activity
  作者：Ikram Chayboun、Ettahir Boulifa、Ahmed Ibn Mansour、Fernando Rodriguez-Serrano、Esther Carrasco、Pablo Juan Alvarez、Rachid Chahboun、Enrique Alvarez-Manzaneda

  DOI：10.1021/np500975b

  日期：2015.5.22

  The first enantiospecific syntheses of neopetrosiquinones A (6) and)3 (7), two merosesquiterpenes isolated from the deep-water sponge Neopetrosia cf proxima, from the labdane diterpene trans-communic acid (10) have been achieved. A key step of the synthetic sequence is the simultaneous aromatization of the C ring and the benzylic oxidation on C-7 of an advanced intermediate, mediated by the oxygen-DDQ system. The in vitro antiproliferative activities of neopetrosiquinone B (7) and of the synthetic intermediates 8 and 9 against human breast (MCF-7), lung (A-549), and colon (T-84) tumor cell lines have been assayed. The most potent was compound 9 (IC50 = 4.1 mu M), which was twice as active as natural compound 7 (IC50 = 8.3 mu M) against A-549 cells. In addition, the treatment with these compounds resulted in an induction of apoptosis. These findings indicate that the terpene benzoquinones reported here might be potentially useful as anticancer agents.
• An Efficient Synthesis of the Antifungal Dilactone LL-Z1271α and of other Biologically Active Compounds
  作者：A Barrero

  DOI：10.1016/00404-0399(50)0949d-

  日期：1995.7.17
• Synthesis of Ambrox® from communic acids
  作者：Alejandro F. Barrero、Joaquín Altarejos、Enrique J. Alvarez-Manzaneda、José M. Ramos、Sofía Salido

  DOI：10.1016/s0040-4020(01)87963-1

  日期：1993.7

  Two routes for preparing Ambrox(R) (1) from the methyl esters of trans-communic acid (2b) and/or cis-communic acid (3b), via selective degradation of their side chains, stereoselective formation of the tetrahydrofurane ring, and reduction of the axial methoxycarbonyl group, are described.
• BARRERO, ALEJANDRO F.;SANCHEZ, JUAN F.;ALTAREJOS, JOAQUIN, TETRAHEDRON LETT., 30,(1989) N0, C. 5515-5518
  作者：BARRERO, ALEJANDRO F.、SANCHEZ, JUAN F.、ALTAREJOS, JOAQUIN

  DOI：——

  日期：——
• Enantiospecific syntheses of the potent bioactives nagilactone F and the mould metabolite LL-Z1271α an evaluation of their allelopathic potential
  作者：Alejandro F Barrero、Juan F Sánchez、Jamal Elmerabet、David Jiménez-González、Francisco A Macías、Ana M Simonet

  DOI：10.1016/s0040-4020(99)00355-5

  日期：1999.6

  Improved syntheses are described for nagilactone F and the antibiotic LL-Z1271 alpha, two of the most potent bioactive members of the podolactone family. The allelopathic potential of some members of this podolactone series has been evaluated, with the result that the metabolite LL-Z1271 alpha is one of the most active compounds. (C) 1999 Elsevier Science Ltd. All rights reserved.