顺式璎柏酸 | 1231-35-2

• 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
• 中文名称: 顺式璎柏酸
• 中文别名: 反式璎柏酸
• 英文名称: (E)-communic acid
• 英文别名: trans-communic acid；(12E)-communic acid；Communic Acid；(1S,4aR,5S,8aR)-1,4a-dimethyl-6-methylidene-5-[(2E)-3-methylpenta-2,4-dienyl]-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid
• CAS: 1231-35-2；2761-77-5；5573-13-7；53109-43-6；60872-81-3；67710-87-6；69427-96-9；83945-57-7；10178-32-2
• 化学式: C₂₀H₃₀O₂
• 分子量: 302.457
• InChiKey: YGBZFOQXPOGACY-VWVSFFKRSA-N

物化性质

• 熔点：
  130-132 °C
• 沸点：
  414.0±34.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

上下游信息

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	(E)-methyl communate	15798-13-7	C21H32O2	316.484
  ——	(1S,4aR,5S,8aR)-1,4a-dimethyl-6-methylidene-5-(2-oxoethyl)-3,4,5,7,8,8a-hexahydro-2H-naphthalene-1-carboxylic acid	426219-76-3	C16H24O3	264.365
  ——	acrostalic acid	55306-07-5	C16H24O4	280.364
  ——	13,14,15,16-tetranorlabda-6,8(17)-diene-12,19-dioic acid	291748-34-0	C16H22O4	278.348
  ——	12S-hydroxylabda-8(17),13(16),14-trien-19-oic acid	366796-98-7	C20H30O3	318.456
  ——	dimethyl 13,14,15,16-tetranorlabd-8(17)-ene-12,19-dioate	39668-50-3	C18H28O4	308.418
  ——	13,14,15,16-tetranorlabda-6,8(17)-diene-12,19-dioic acid 12-methyl ester	291748-44-2	C17H24O4	292.375
  ——	dimethyl 13,14,15,16-tetranorlabda-6,8(17)-diene-12,19-dioate	291748-33-9	C18H26O4	306.402
  ——	(4S,5R,9S,10R,12R)-12,15-epoxylabda-8(17),13-dien-19-oic acid	946416-19-9	C20H30O3	318.456
  ——	(4S,5R,9S,10R,12R)-methyl 12,15-epoxylabda-8(17),13-dien-19-oate	1448547-72-5	C21H32O3	332.483

反应信息

• 作为反应物：
  描述：

  顺式璎柏酸 在 四(三苯基膦)钯 chromium(VI) oxide 、 叔丁基过氧化氢 、 4-二甲氨基吡啶 、 selenium(IV) oxide 、 硫酸 、 氧气 、 potassium carbonate 、 臭氧 、 1-丙烷硫醇钠 作用下， 以 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 42.25h， 生成 13,14,15,16-tetranorlabda-6,8(17)-diene-12,19-dioic acid
  参考文献：
  名称：

  First Synthesis of the Antifungal Oidiolactone C from trans-Communic Acid:  Cytotoxic and Antimicrobial Activity in Podolactone-Related Compounds

  摘要：

  The synthesis of the fungicide oidiolactone C starting from diterpenic trans-communic acid was carried out with an overall yield of 11.7%. The key step in the process consists of a new bislactonization reaction catalyzed by Pd(H), which gives rise to the podolactone-type tetracyclic skeleton from a norlabdadienedioic acid. We also carried out a study of the structure-biological activity of different natural podolactones and their synthetic precursors. Thus, the highest cytotoxic activity was found in dienic dilactones with ether-type substitutions on C-17, whereas the closure of the gamma-lactone ring is not critical for presenting a maximal antimicrobial activity.

  DOI：

  10.1021/jo0161882

文献信息

• 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。
• Anti-tumor Promoting Diterpenes from the Stem Bark of Thuja standishii (Cupressaceae)
  作者：Manabu Iwamoto、Hironori Ohtsu、Harukuni Tokuda、Hoyoku Nishino、Shunyo Matsunaga、Reiko Tanaka

  DOI：10.1016/s0968-0896(01)00099-2

  日期：2001.7

  Three new labdane-type diterpenoids, labda-8(17),13-dien-15,12R-olid-19-oic acid (1), 12S-hydroxylabda-8(17),13(16),14-trien-19-oic acid (2) and 13-ethoxylabda-8(17),11,14-trien-19-oic acid (3), along with known diterpenoids, trans-communic acid (4), totarol (5), 12-methoxyabieta-8,11,13-trien-11-ol (6), and 7 alpha,8 alpha-epoxy-6 alpha-hydroxyabieta-9(11),13-dien-12-one (7) were isolated from the

  三个新的拉丹烷型二萜类化合物，labda-8（17），13-dien-15,12R-olid-19-oic acid（1），12S-hydroxylabda-8（17），13（16），14-trien- 19-油酸（2）和13-乙氧基labda-8（17），11,14-三烯-19-油酸（3），以及已知的二萜类化合物，反式-甲酸（4），甲苯酚（5），12从以下产品中分离出-methoxymethoxyaeta-8,11,13-trien-11-ol（6）和7个alpha，8 alpha-epoxy-6 alpha-hydroxyabieta-9（11），13-dien-12-one（7）金钟柏的茎皮。通过光谱法和化学转化来建立1--3的结构。测试了这些化合物与立式（8），12-羟基-6,7-seco-abieta-8,11,13-trien-6,7-二聚体（9）和6α-羟基sugiol（10
• Syntheses and Structural Confirmations of Members of a Heterocycle-Containing Family of Labdane Diterpenoids
  作者：Daniel J. Mack、Jon T. Njardarson

  DOI：10.1002/anie.201208412

  日期：2013.1.28

  Building with berries! Several labdane natural products have been synthesized for the first time by the combination of a copper‐catalyzed vinyl oxirane ring expansion reaction with an abundant, inexpensive, chiral natural source (juniper berries; see scheme). These expedient (1–5 step) syntheses have resulted in the structural confirmations of five natural products and one reassignment. Reagent‐controlled

  用浆果建造！通过将铜催化的乙烯基环氧乙烷扩环反应与丰富、廉价的手性天然来源（杜松子；参见方案）相结合，首次合成了几种拉丹烷天然产物。这些权宜之计（1-5 步）合成导致了五种天然产物的结构确认和一种重新分配。还提供了试剂控制的氧化和 1,3-二烯异构化结果。
• Diterpenes and flavonoids as 5-alpha-reductase inhibitors
  申请人：Kabushiki Kaisha Yakurigaku Chuo Kenkyusho

  公开号：EP0747048A2

  公开（公告）日：1996-12-11

  Strong 5α-reductase inhibitors are extracted and fractionated from Thuja orientalisis and other similar crude drugs or they may be purified as diterpenes in isolated form. The inhibitors are used either on their own or as active ingredients of therapeutics in the treatment of diseases caused by the overactivity of 5α-reductase or the hypersecretion of androgens, such as male pattern baldness, androgenetic alopecia, hirsutism, acne, prostatomegaly and cancer of the prostate.

  强烈的 5α 还原酶抑制剂是从东方蒺藜和其他类似的粗制药物中提取和分馏出来的，也可以分离纯化为二萜。这些抑制剂可单独使用，也可作为治疗药物的活性成分，用于治疗因 5α 还原酶过度活跃或雄激素分泌过多而引起的疾病，如男性秃发、雄激素性脱发、多毛症、痤疮、前列腺肥大和前列腺癌。
• ROSIN-MODIFIED PHENOL RESIN, PROCESS FOR PRODUCTION THEREOF, VARNISH FOR PRINTING INK, AND PRINTING INK
  申请人：Arakawa Chemical Industries, Ltd.

  公开号：EP2573123A1

  公开（公告）日：2013-03-27

  A rosin-modified phenolic resin, which consists of a reaction product among (a) a rosin that contains a component derived from communic acid in an amount of 0.1 to 0.8wt%, (b) a condensation product of a phenol and formaldehyde, and (c) a polyol. The rosin-modified phenol resin makes it possible to produce a printing ink which has a good balance among ink performances such as fluidity, emulsification resistance, misting resistance, drying properties, and gloss.

  一种松香改性酚醛树脂，它由以下物质的反应产物组成：(a) 松香，松香中含有 0.1 至 0.8wt% 的交流酸成分；(b) 苯酚和甲醛的缩合产物；(c) 多元醇。松香改性酚醛树脂可以生产出在流动性、抗乳化性、抗雾性、干燥性能和光泽度等油墨性能之间具有良好平衡的印刷油墨。