methyl 12-oxo-13,14,15,16-tetranorlabd-8(17)-en-19-oate | 39668-54-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 12-oxo-13,14,15,16-tetranorlabd-8(17)-en-19-oate
• 英文别名: methyl (1S,4aR,5S,8aR)-1,4a-dimethyl-6-methylidene-5-(2-oxoethyl)-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylate
• CAS: 39668-54-7
• 化学式: C₁₇H₂₆O₃
• 分子量: 278.392
• InChiKey: WNBWIZVJMQGNLE-ABFRBSLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  20
• 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：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 12-oxo-13,14,15,16-tetranorlabd-8(17)-en-19-oate 在 chromium(VI) oxide 、 硫酸 、 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 、 丙酮 、 苯 为溶剂， 反应 18.5h， 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 13,14,15,16-tetranorlabd-8(17)-ene-12,19-dioate 在 红铝 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 20.5h， 生成 methyl 12-oxo-13,14,15,16-tetranorlabd-8(17)-en-19-oate
  参考文献：
  名称：

  Cambie, Richard C.; Clark, George R.; Goeth, Michelle E., Australian Journal of Chemistry, 1989, vol. 42, # 4, p. 497 - 510

  摘要：

  DOI：

文献信息

• Stereoselective Barbier-Type Allylations and Propargylations Mediated by CpTiCl₃
  作者：Josefa L. López-Martínez、Irene Torres-García、Ignacio Rodríguez-García、Manuel Muñoz-Dorado、Miriam Álvarez-Corral

  DOI：10.1021/acs.joc.8b02643

  日期：2019.1.18

  CpTiCl2, prepared in situ by manganese reduction of CpTiCl3, is an excellent new system for the Barbier-type allylation and propargylation of carbonyl compounds. It can be used in catalytic amounts when combined with Et3N·HBr/TMSBr, which acts as a regenerating system. The high regio- and stereoselectivity shown by this system makes it useful for prenylation and crotylation processes in the synthesis

  CpTiCl 2，由锰还原CpTiCl的原位制备3，是用于羰基化合物的巴比尔型烯丙基炔丙基和优异的新系统。与再生系统Et 3 N·HBr / TMSBr结合使用时，可以催化量使用。该系统显示的高区域选择性和立体选择性使其可用于天然产物合成中的异戊二烯化和丁二酰化过程。
• Synthesis of Phenol Abietane Diterpenes Based on the Oxidative Radical Cyclization Utilizing the Mn(OAc)₃/Ac₂O System
  作者：Enrique Alvarez-Manzaneda、Rachid Chahboun、Eduardo Cabrera、Esteban Alvarez、Ramón Alvarez-Manzaneda、Mohammed Lachkar、Ibtissam Messouri

  DOI：10.1055/s-2007-985586

  日期：2007.9

  A new route to phenol abietane diterpenes from trans-communic acid is reported. The key step is the transformation of a β-ketoester into the corresponding O-acetylsalicilate, via a manganese(III)-based oxidative free-radical cyclization carried out in AC 2 O. Utilizing this, the first synthesis of (-)-sugikurojin A has been achieved. The immunosuppressor 19-hydroxyferruginol has also been synthesized

  报道了从反式通信酸制备苯酚松香烷二萜的新途径。关键步骤是通过在 AC 2 O 中进行基于锰 (III) 的氧化自由基环化反应，将 β-酮酯转化为相应的 O-乙酰水杨酸酯。利用这一点，首次合成了 (-)-sugikurojin A 已经达到。还合成了免疫抑制剂 19-羟基铁黄醇。
• A New Synthesis of a Potent Cancer Chemopreventive Agent, 13-Oxo-15,16-dinorlabda-8(17),11E-dien-19-oic Acid from trans-Communic Acid.
  作者：Takahiro Katoh、Reiko Tanaka、Masatoshi Takeo、Kiyoharu Nishide、Manabu Node

  DOI：10.1248/cpb.50.1625

  日期：——

  The first synthesis of a labdane diterpenoid, (-)-13-oxo-15,16-dinorlabda-8(17),11E-dien-19-oic acid [(-)-1a], isolated from the stem bark of Thuja standishii (GORD.) CARR., from the major component trans-communic acid (3a) is described.

  从金钟柏茎皮中分离出来的拉丹烷二萜，（-）-13-oxo-15,16-dinorlabda-8（17），11E-dien-19-oic acid [（-）-1a]描述了由主要成分反式-共用酸（3a）制成的standishii（GORD。）CARR。
• 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