(+)-albicanic acid methyl ester | 112709-39-4

• 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: (+)-albicanic acid methyl ester
• 英文别名: methyl (1R,4aR,8aR)-5,5,8a-trimethyl-2-methylidene-3,4,4a,6,7,8-hexahydro-1H-naphthalene-1-carboxylate
• CAS: 112709-39-4
• 化学式: C₁₆H₂₆O₂
• 分子量: 250.381
• InChiKey: OGTZZPDGRYENGN-DVOMOZLQSA-N

物化性质

• 沸点：
  299.4±19.0 °C(Predicted)
• 密度：
  0.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+)-albicanic acid methyl ester 在 lithium aluminium tetrahydride 、 Candida cylindracea lipase (24.2 U/mg) 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 醋酸奥曲肽杂质
  参考文献：
  名称：

  Studies in Lipase Catalyzed Transesterifications: Synthesis of (+)-Albicanol, (+)-Albicanyl Acetate and Chiral Intermediates Useful in the Synthesis of Drimanes and Labdanes

  摘要：

  Chiral intermediates [(-)-8, (+)-9, (-)-9, (+)-10, (-)-10, (+)-11] useful in the synthesis of drimanes and labdanes, as well as optically active albicanol 1 and albicanyl acetate 2, have been synthesized using enzymatic transesterification as the key step. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00096-x
• 作为产物：
  描述：

  香叶基丙酮 在 四氯化锡 、 sodium hydride 、 sodium amide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 16.25h， 生成 (+)-albicanic acid methyl ester
  参考文献：
  名称：

  Phenol Benzylic Epoxide to Quinone Methide Electron Reorganization: Synthesis of (.+-.)-Taxodone

  摘要：

  The total synthesis of(+/-)-taxodone (1) is described. The C-ring is formed by the cycloaddition of methyl acrylate with furan 8, the latter derived from isodrimenin. The C13 isopropyl group was introduced via a sulfur ylide rearrangement followed by reductive cleavage. Compound I was synthesized in 61% yield by deprotection and intramolecular oxirane opening of diacetate 31 with potassium tert-butoxide and water in THF.

  DOI：

  10.1021/jo00097a057

文献信息

• Synthesis of a novel sphingosine kinase inhibitor (−)-F-12509A and determination of its absolute configuration
  作者：Nobuhiro Maezawa、Noriyuki Furuichi、Hiroshi Tsuchikawa、Shigeo Katsumura

  DOI：10.1016/j.tetlet.2007.05.043

  日期：2007.7

  The synthesis of a novel sphingosine kinase inhibitor, (−)-F-12509A ((−)-1), was achieved in a highly efficient manner that included nine longest linear steps and 45% overall yield from (−)-bicyclic β-ketoester (−)-2, and its absolute configuration was determined to be (5S,9S,10S).

  新型鞘氨醇激酶抑制剂（-）-F-12509A（（-）- 1）的合成以高效的方式完成，该方法包括九个最长的线性步骤，且从（-）-双环β-的总收率达45％酮酸酯（-）- 2，其绝对构型确定为（5 S，9 S，10 S）。
• Preparation of 9α-Fluorinated Sesquiterpenic Drimanes and Evaluation of Their Antifeedant Activities
  作者：Antonio Abad、Consuelo Agulló、Ana C. Cuñat、Azucena González-Coloma、David Pardo

  DOI：10.1002/ejoc.200901499

  日期：2010.4

  of 9α-fluoro analogues of both natural and unnatural drimane-type sesquiterpenes is described. Their synthesis began with the initial preparation of methyl 8-keto-12-nordriman-11-oate from β-ionone and entailed the electrophilic fluorination of C-9 for the stereoselective introduction of the fluorine atom. The drimane skeleton was completed from the intermediate 9α-fluoro-8-keto-12-nordrimane system

  描述了天然和非天然 drimane 型倍半萜的 9α-氟类似物的制备。他们的合成开始于从 β-紫罗兰酮初步制备 8-keto-12-nordriman-11-oate 甲酯，并需要对 C-9 进行亲电氟化以立体选择性地引入氟原子。drimane 骨架由中间体 9α-fluoro-8-keto-12-nordrimane 体系通过 C-8 酮羰基上的不同反应完成，主要是 Wittig 亚甲基化、氰醇形成或钯催化的相应烯醇三氟甲磺酸酯的羰基化. 对源自这些关键反应的官能化进行进一步操作，可以制备 9α-氟代二甲醚，其在结构和功能上与 albicanic acid、drimenin 和 olepupuane 相关。
• Total synthesis of the marine sesquiterpene hydroquinones zonarol and isozonarol and the sesquiterpene quinones zonarone and isozonarone
  作者：Jörg Schröder、Christine Magg、Karlheinz Seifert

  DOI：10.1016/s0040-4039(00)00891-1

  日期：2000.7

  The total synthesis of the naturally occurring sesquiterpene hydroquinones zonarol and isozonarol and the sesquiterpene quinones zonarone and isozonarone was achieved starting from β-ionone, which was transformed via (+)-albicanic acid to (+)-albicanal and (−)-drim-7-en-11-al. Coupling of the aldehydes with lithiated hydroquinone ethers and further modification of the coupling products led to the target

  天然倍半萜烯对苯二酚唑纳洛尔和异唑烷酮以及倍半萜烯醌佐那隆和异唑烷酮的全合成是从β-紫罗兰酮开始的，β-紫罗兰酮通过（+）-白蚁酸转化为（+）-白三醛和（-）-drim- 7-en-11-al。醛与锂化对苯二酚醚的偶联以及偶联产物的进一步修饰产生了目标分子。
• Total Synthesis of the Marine Sesquiterpene Quinones Hyatellaquinone and Spongiaquinone
  作者：Andreas Bernet、Jörg Schröder、Karlheinz Seifert

  DOI：10.1002/hlca.200390158

  日期：2003.6

  The synthesis of the marine sesquiterpene quinone (+)-hyatellaquinone (1) was achieved starting from the sesquiterpene aldehyde (+)-albicanal ((+)-3) (Schemes 3 and 4). Coupling of (+)-albicanal with 2,3,5,6-tetramethoxyphenyllithium led to the aryl-sesquiterpene system, which was modified to the target molecule. Furthermore, the first total synthesis of the marine compound spongiaquinone (2) was carried

  从倍半萜醛（+）-白色醛（（+）- 3）（方案3和4）开始，实现了海洋倍半萜烯醌（+）-杂萘醌（1）的合成。（+）-白色醛与2,3,5,6-四甲氧基苯基锂的偶联导致芳基-倍半萜烯系统，该系统被修饰为目标分子。此外，海洋化合物海绵醌（2）的第一个全合成是从（（-）-白色（3）-3）开始的，其反应顺序包括立体选择性CC键加氢和一锅AcOH消除/去甲基化反应（方案7和10）。1和2的1,2-和1,4-苯醌形式的出现取决于溶剂系统的pH值。
• First synthesis of (−)-spongianolide A and determination of its absolute structure
  作者：Toshiyuki Hata、Katsunori Tanaka、Shigeo Katsumura

  DOI：10.1016/s0040-4039(99)00039-8

  日期：1999.2

  The first synthesis of (−)-spongianolide A (1), a cytotoxic sesterterpenoid, and determination of its absolute structure are described. In this synthesis, a simple and practical method for preparation of enantiomerically pure bicyclic and tricyclic β-ketoesters, and a new Wittig reagent, furanmethylide, were developed.

  描述了（-）-海绵状内酯A（1）的首次合成，细胞毒性的酯类萜类化合物及其绝对结构的确定。在该合成中，开发了一种简单，实用的对映体纯的双环和三环β-酮酸酯的制备方法，并开发了一种新的Wittig试剂呋喃甲基化物。