(10S,14R)-(-)-isoagath-12-en-15-ol | 59909-44-3

• 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: (10S,14R)-(-)-isoagath-12-en-15-ol
• 英文别名: (14R)-isoagath-12-en-15-ol；(14S)-isoagath-12-en-15-ol；isoanticopal-12-en-15-ol；1.1.4ar.7c.8ac-Pentamethyl-8c-hydroxymethyl-(4btH.10atH)-Δ⁶-dodekahydro-phenanthren；14-Hydroxymethyl-8β,13-dimethylpodocarpan；[(1R,4aR,4bS,8aS,10aR)-2,4b,8,8,10a-pentamethyl-4,4a,5,6,7,8a,9,10-octahydro-1H-phenanthren-1-yl]methanol
• CAS: 59909-44-3
• 化学式: C₂₀H₃₄O
• 分子量: 290.489
• InChiKey: URRUSDHNWZECKY-ORZNMBHWSA-N

物化性质

• 熔点：
  110-113 °C
• 沸点：
  371.0±11.0 °C(Predicted)
• 密度：
  0.942±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (10S,14R)-(-)-isoagath-12-en-15-ol 在 四丙基高钌酸铵 对甲苯磺酸 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 3.0h， 生成 isoanticopal-13-en-15-al
  参考文献：
  名称：

  Synthesis of Three Marine Natural Sesterterpenolides from Methyl Isoanticopalate. First Enantioselective Synthesis of Luffolide

  摘要：

  The synthesis of three marine sponge metabolites, luffolide (4), 5, and 6, are described for the first time, establishing the absolute configuration of these compounds. The key intermediate, aldehyde 17, wash obtained from methyl isoanticopalate, 11. The addition of 3-furyllithium to 17 and subsequent photochemical oxidation give the gamma-hydroxybutenolide 5 and its epimer at C-16. Sesterterpenolide 6 is obtained by dehydration of 5. From the key aldehyde 17, luffolide (4) was obtained in six steps.

  DOI：

  10.1021/jo0515529
• 作为产物：
  描述：

  香叶基香叶醇 在 Alicyclobacillus acidocaldarius squalene-hopene cyclase 、 Triton X-100 作用下， 反应 16.0h， 以6.3 mg的产率得到(10S,14R)-(-)-isoagath-12-en-15-ol
  参考文献：
  名称：

  Enzymatic cyclization reactions of geraniol, farnesol and geranylgeraniol, and those of truncated squalene analogs having C₂₀and C₂₅by recombinant squalene cyclase

  摘要：

  使用 C10-C25 类似物（包括天然物质，如香叶醇（C10）、法呢醇（C15）和香叶基香叶醇（C20））研究了角鲨烯-蒎烯环化酶的底物特异性。香叶醇没有发生环化反应，但法尼醇的转化率却很高（64%），产生了由 6/6 融合双环系统组成的环状倍半萜化合物。在这些化合物中，产生了一种具有吸引力的 C30 化合物，其结构中的非环芳樟醇单元通过醚键与双环骨架相连。香叶醇的转化率很低（约为 12%）。具有 C20 和 C25 的角鲨烯类似物也被环化，收率约为 33-36%。C(7)-Me和/或C(11)-Me的立体体积较大，在所有前椅构象中都呈α-排列，因此会与靠近C(7)和/或C(11)的环化酶识别位点发生排斥作用，导致无法在反应腔内构建全椅构象。香叶基苯二酚的产量相对较低，这表明必须在 C(14)处设置一个不太笨重的氢原子，才能有效地进行多环化反应。角鲨烯环化酶的底物特异性非常广泛，除了 C30 外，还能接受碳链长度为 C15-C25 的截短类似物。

  DOI：

  10.1039/b407001a

文献信息

• Superacidic cyclisation–lipase-mediated kinetic resolution as a short route from achiral linear isoprenoid alcohols to scalemic cyclic isomers
  作者：Edward P. Serebryakov、Galina D. Gamalevich、Veacheslav N. Kulcitki、Nicon D. Ungur、Pavel F. Vlad

  DOI：10.1070/mc2002v012n02abeh001566

  日期：2002.1

  (+/-)-alpha-Cyclogeraniol and (+/-)-drim-7-en-11-ol acetates obtained via the FSO3H-induced cyclisation of geraniol and (E)-farnesol and subsequent acetylation were hydrolysed in the presence of hog pancreas lipase (PPL) to afford (R)-(+)-alpha-cyclogeraniol (ee similar to30% at the optimal conversion C = 20+/-2%) and (5R,9R,10R)-(+)-drim-7-en-11-ol (ee 78.5% at C = 30%), respectively; (+/-)-15-acetoxy-isoagath-12-ene, obtained similarly from all-E-geranylgeraniol, is resistant to PPL-mediated hydrolysis, but is hydrolysed in the presence of lipase from Candida cylindracea to afford (10S,14R)-(-)-isoagath-12-en-15-ol of 69-80% ee in similar to3% yield.

  (+/−)-α-环瑞香醇和(+/−)-7-降-11-醇乙酸酯通过发烟硫酸(FSO3H)诱导的茉莉醇和(E)-法尼醇的环化反应，随后经乙酰化制得；在猪胰脂酶(PPL)存在下水解，分别得到(R)-(+)-α-环瑞香醇(在最优转化率C = 20±2%时，ee ≈30%)和(5R,9R,10R)-(+)-7-降-11-醇(在C = 30%时，ee 为78.5%);而(+/-)-15-乙酸氧-异灰独木烯-12-烯，由全顺式-香叶基香叶醇类似制得，在PPL介导下对水解具有抗性，但在来自于Candida cylindracea的脂酶存在下水解，以≈3%的收率得到(10S,14R)-(-)-异灰独木烯-12-烯-15-醇，ee为69-80%。
• Chemical studies of british columbia nudibranchs
  作者：Kirk Gustafson、Raymond J. Andersen

  DOI：10.1016/s0040-4020(01)96478-6

  日期：1985.1

  The chemical constituents of the skin extracts of several nudibranchs have been examined. Extracts of Archidoris montereyensis contain the diterpenoic acid glyceride 20, its two monoacetates 24 and 25, the drimane sesquiterpenoic acid glyceride 26, the monoacetate 28, the monocyclofarnesic acid glyceride 30 and the glyceryl ether 31. Glyceride 20 has also been isolated from extracts of Archidoris odhneri

  已经检查了几种裸露分支的皮肤提取物的化学成分。满天星（Archidoris montereyensis）的提取物包含二萜酸甘油酯20，其两个单乙酸酯24和25，drimane倍半萜烯酸甘油酯26，单乙酸酯28，单环法酸甘油酯30和甘油醚31。甘油20也已从Archidoris odhneri的提取物中分离出来。Amsodoris nobilis提取物的气味原理被证明是降解的倍半萜类化合物33。聚三色提取物含有三氮磷（19）作为其主要成分。14 C标记的甲羟戊酸掺入二萜附加甘油酯20和sesquiterpenoic酸甘油酯26由A. montereyensis，并进入famesic附加甘油酯12由A. odhneri。十二烷酸加甘油酯26和甘油醚31对潮汐池的头皮Oligocottus maculosus具有拒食活性。
• Terpenoic acid glycerides from the dorid nudibranch
  作者：Kirk Gustafson、Raymond J. Andersen、Marie H.M. Chen、Jon Clardy、Jill E. Hochlowski

  DOI：10.1016/s0040-4039(01)91135-9

  日期：1984.1

  Extracts of the dorid nudibranch contain a diterpenoic acid glyceride 1 whose structure has been determined by x-ray diffraction analysis. The structure of a minor metabolite, the sesquiterpenoic acid glyceride 2, was determined by chemical correlation.

  苦丁香的提取物含有二萜酸甘油酯1，其结构已通过X射线衍射分析确定。通过化学相关性确定次要代谢产物倍半萜酸甘油酯2的结构。
• Chemoenzymatic synthesis of (+)-isoagatholactone, (+)-spongian-16-one, and 3-deoxychavalone A <i>via</i> biocatalytic polyene cyclization
  作者：Wen Xiao、Su-Jing Wang、Ming-Zhu Yu、Xue-Jie Zhang、Zheng Xiang

  DOI：10.1039/d3ob00206c

  日期：——

  The stereoselective cyclization of geranylgeraniol catalysed by squalene-hopene cyclase (SHC) was investigated. By use of this transformation, spongiane diterpenoids (+)-isoagatholactone and (+)-spongian-16-one, and meroterpenoid 3-deoxychavalone A were synthesized in a concise and redox-economic manner. This work showcases the application of SHC-catalysed cyclization as a key step in terpenoid synthesis

  研究了角鲨烯-藿烯环化酶（SHC）催化香叶基香叶醇的立体选择性环化反应。通过该转化，以简洁且氧化还原经济的方式合成了海绵二萜(+)-isoagatholactone和(+)-spongi-16-one，以及类萜3-脱氧查瓦酮A。这项工作展示了 SHC 催化环化作为萜类化合物合成关键步骤的应用。
• The first synthesis of marine sesterterpene (+)-scalarolide
  作者：Xiang-Jian Meng、Yang Liu、Wen-Yuan Fan、Bin Hu、Wenting Du、Wei-Ping Deng

  DOI：10.1016/j.tetlet.2009.06.064

  日期：2009.9

  The synthesis of the first example of C12 oxygenated marine scalaranic sesterterpenes (+)-scalarolide was achieved through three key steps including the ring-opening rearrangement of epoxide, stereoselective Diels-Alder addition and one-pot gamma-butenolide formation process, and the absolute configuration of natural scalarolide was confirmed. (C) 2009 Elsevier Ltd. All rights reserved.