podocarpa-8,11,13-trien-12,13-diol | 157318-11-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: podocarpa-8,11,13-trien-12,13-diol
• 英文别名: (+)-7-deoxynimbidiol；(+)-deoxynimbidiol；7-deoxo nimbidiol；7-deoxynimbidiol；(4bS,8aS)-4b,8,8-trimethyl-5,6,7,8a,9,10-hexahydrophenanthrene-2,3-diol
• CAS: 157318-11-1
• 化学式: C₁₇H₂₄O₂
• 分子量: 260.376
• InChiKey: KXJMADAZFTXYKB-DOTOQJQBSA-N

物化性质

• 熔点：
  90-92 °C(Solv: ligroine (8032-32-4); ethyl acetate (141-78-6))
• 沸点：
  396.9±42.0 °C(Predicted)
• 密度：
  1.092±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 podocarpa-8,11,13-trien-12,13-diol 以 乙醚 为溶剂， 生成 12,13-dimethoxypodocarpa-8,11,13-triene
  参考文献：
  名称：

  First formal synthesis of (+)-nimbidiol. Synthesis, X-ray structure and anticancer activity of a novel ring C aromatic diterpene: dimethyl (+)-podocarpa-8,11,13-triene-12,13-dicarboxylate

  摘要：

  A novel ring C aromatic diterpene (4) has been prepared in three steps from natural (+)-manool (1). The structure and anticancer activity data for 4 has been investigated. This key intermediate (4) was easily transformed into 7-deoxo nimbidiol dimethyl ether (8). The present work represents the first formal synthesis of (+)-nimbidiol (10). (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00105-9
• 作为产物：
  描述：

  Δ⁸⁽¹⁴⁾-podocarpen-13-one 在 potassium carbonate 、 溶剂黄146 、 lithium bromide 、 copper(ll) bromide 作用下， 以 甲醇 、 乙腈 、 苯 为溶剂， 反应 49.0h， 生成 podocarpa-8,11,13-trien-12,13-diol
  参考文献：
  名称：

  环 C 芳香二萜的简便合成：(+)-13-Hydroxypodocarpa-8,11,13-triene 和 (+)-7-Deoxynimbidiol 的合成

  摘要：

  摘要 已从 (+)-manool 4 方便地合成天然 (+)-13-hydroxypodocarpa-8,11,13-triene 1 和 (+)-7-deoxynimbidiol 2 已实现良好的总收率。

  DOI：

  10.1080/00397911.2010.492078

文献信息

• Syntheses and Antibacterial Activities of Diterpene Catechol Derivatives with Abietane, Totarane and Podocarpane Skeletons against Methicillin-Resistant Staphylococcus aureus and Propionibacterium acnes
  作者：Masahiro Tada、Jun Kurabe、Takashi Yoshida、Tomoyuki Ohkanda、Yusuke Matsumoto

  DOI：10.1248/cpb.58.818

  日期：——

  Natural catechol, quinone and quinone methide diterpenes with abietane (15-deoxyfuerstione, taxodione) and totarane (dispermone, 12,13-dihydroxy-8,11,13-totaratriene-6-one), and podocarpane (nimbidiol, deoxynimbidiol) skeletons were synthesized using ortho-oxidation of phenol with meta-chlorobenzoyl peroxide. Minimum inhibitory activities of these diterpenes and previously synthesized natural diterpenes were measured against methicillin-resistant Staphylococcus aureus (MRSA) and Propionibacterium acnes, which cause serious skin infection associated with acne. Abietaquinone methide and 8,11,13-totaratriene-12,13-diol showed potent activities against S. aureus (MRSA) and P. acnes, and no serious toxicity by oral dose to mice.

  天然儿茶酚、醌和醌甲烯二萜类化合物，具有雪松烃（15-去氧福尔斯特酮、税烯酮）和托塔烃（分散酮、12,13-二羟基-8,11,13-托塔烯-6-酮）以及桃金娘烃（宁比二醇、去氧宁比二醇）骨架，通过对苯酚进行邻位氧化，使用对氯苯甲酰过氧化物合成。此外，测量了这些二萜及之前合成的天然二萜对耐甲氧西林金黄色葡萄球菌（MRSA）和丙酸杆菌的最低抑菌活性，这些细菌引起与痤疮相关的严重皮肤感染。Abieta醌甲烯和8,11,13-托塔烯-12,13-二醇对金黄色葡萄球菌（MRSA）和丙酸杆菌显示出强效活性，并且在口服给药于小鼠时没有严重毒性。
• Facile Access to Optically Active Ring C Aromatic Diterpenes from (+)-manool. Synthesis of (+)-13-Hydroxypodocarpa-8,11,13-Triene, (+)-7-Deoxynimbidiol and (+)-Nimbidiol
  作者：José E. Villamizar、Crisbel Montiel、Carlos Gamez、Antonio Alcalá、Yurimar Herrera、Franklin Salazar、Eleonora Tropper、Nieves Canudas

  DOI：10.3184/030823410x12792754099464

  日期：2010.8

  A practical method for the synthesis of naturally occurring ring C aromatic diterpenes from (+)-manool via key intermediate β-enone is described. The natural (+)-13-hydroxypodocarpa-8,11,13-triene, the antitumour (+)-7-deoxynimbidiol, and (+)-nimbidiol were prepared in good overall yields.

  描述了通过关键中间体 β-烯酮从 (+)-manool 合成天然存在的 C 环芳族二萜的实用方法。天然 (+)-13-hydroxypodocarpa-8,11,13-triene、抗肿瘤 (+)-7-deoxynimbidiol 和 (+)-nimbidiol 以良好的总产率制备。
• Novel synthetic strategy toward abietane and podocarpane-type diterpenes from (−)-sclareol: synthesis of the antitumor (+)-7-deoxynimbidiol
  作者：Enrique Alvarez-Manzaneda、Rachid Chahboun、Eduardo Cabrera、Esteban Alvarez、Ramón Alvarez-Manzaneda、Mohammed Hmamouchi、Hakima Es-Samti

  DOI：10.1016/j.tetlet.2007.10.080

  日期：2007.12

  to abietane and podocarpane-type terpenoids from labdane diterpenes is reported. The key step is the transformation of β-ketoester 9 into the corresponding O-acetylsalicylate ester 18, via a manganese(III)-based oxidative free-radical cyclization carried out in Ac2O. Utilizing this, the synthesis of the antitumor (+)-7-deoxynimbidiol (5) from (−)-sclareol (11) has been achieved. (+)-Nimbidiol (6) and

  据报道，从拉丹烷二萜类化合物中获得一种新的松果烷和罗汉松类萜类化合物的途径。关键步骤是通过在Ac 2 O中进行的基于锰（III）的氧化自由基环化反应，将β-酮酸酯9转变为相应的O-乙酰基水杨酸酯18。从（-）-香紫苏醇（11）获得了）-7-脱氧亚氨基二醇（5）。还已经合成了（+）-二丙二醇（6）和天然萜类化合物20。
• Bendall, Justin G.; Cambie, Richard C.; Rutledge, Peter S., Australian Journal of Chemistry, 1994, vol. 47, # 3, p. 487 - 500
  作者：Bendall, Justin G.、Cambie, Richard C.、Rutledge, Peter S.、Stevenson, Ralph J.、Woodgate, Paul D.

  DOI：——

  日期：——
• Facile and Simple Synthesis of Ring C Aromatic Diterpenes: Synthesis of (+)-13-Hydroxypodocarpa-8,11,13-triene and (+)-7-Deoxynimbidiol
  作者：José E. Villamizar、Carlos Gamez、Antonio Alcalá、Franklin Salazar、Eleonora Tropper、Ana Angarita、Nieves Canudas

  DOI：10.1080/00397911.2010.492078

  日期：2011.5.4

  Abstract A convenient synthesis of the natural (+)-13-hydroxypodocarpa-8,11,13-triene 1 and (+)-7-deoxynimbidiol 2 from (+)-manool 4 has been achieved in good overall yield.

  摘要 已从 (+)-manool 4 方便地合成天然 (+)-13-hydroxypodocarpa-8,11,13-triene 1 和 (+)-7-deoxynimbidiol 2 已实现良好的总收率。