Ethyl (2E,4E,6R)-4,6-dimethyl-2,4-dodecadienoic acid | 152984-48-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Ethyl (2E,4E,6R)-4,6-dimethyl-2,4-dodecadienoic acid
• 英文别名: (2E,4E,6R)-4,6-Dimethyldodeca-2,4-dienoic acid；6-(R)-4,6-dimethyldodecadienoic acid；4,6R-dimethyldodeca-2E,4E-dienoic acid；(6R)-4,6-dimethyl-2,4-dodecadienoic acid
• CAS: 152984-48-0
• 化学式: C₁₄H₂₄O₂
• 分子量: 224.343
• InChiKey: JMQOJXLPKZQPAB-FHYDJSHKSA-N

物化性质

• 沸点：
  347.3±11.0 °C(Predicted)
• 密度：
  0.928±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Ethyl (2E,4E,6R)-4,6-dimethyl-2,4-dodecadienoic acid 在 二异丁基氢化铝 、 三乙胺 、 二苯基次膦酰氯 作用下， 以 四氢呋喃 为溶剂， 生成 (2E,4E,6R)-N-[(2S)-1-(4-hydroxyphenyl)-3-oxopropan-2-yl]-4,6-dimethyldodeca-2,4-dienamide
  参考文献：
  名称：

  新型抗生素aranorosin的简明合成

  摘要：

  描述了新型抗生素阿糖胞苷的简短合成，其在关键步骤中采用了新的高价碘介导的酪氨酸衍生物的氧化羟基化作用。采用类似的方法制备6'-表皮阿拉伯糖球蛋白，因此建立了天然化合物的立体化学。

  DOI：

  10.1016/s0040-4039(00)73870-6
• 作为产物：
  描述：

  (R)-2-methyloctan-1-ol 生成 Ethyl (2E,4E,6R)-4,6-dimethyl-2,4-dodecadienoic acid
  参考文献：
  名称：

  隔离和gymnastatin N，一个polo样从真菌激酶1种活性成分的总合成Arachniotus毛虫

  摘要：

  针对POLO样激酶1（Plk1）（一种抗癌靶标）的高通量筛选，鉴定了一种来自点状真菌Arachniotus punctatus的活性提取物。生物测定指导的分馏导致分离出新的天然产物gymaststatin N（1）和已知的化合物阿诺洛糖醇A（2），IC 50值分别为13和118μM 。分离出金格他汀N，3的12'-羟基类似物作为次要成分。Gymnastatin N（1）被认为是（1的52:48混合物小号，6' - [R ）和（1 - [R，6' - [R）非对映异构体，可以合成四种可能的非对映异构体，并比较每种非对映异构体与天然产物的旋光度和手性HPLC谱。合成了类似物1并针对Plk1分析进行了评估，这些SAR研究表明，二烯和游离羧酸部分可能是其生物活性的原因。

  DOI：

  10.1016/j.tet.2004.09.046

文献信息

• A concise synthesis of the novel antibiotic aranorosin
  作者：Alexander McKillop、Lee McLaren、Robert J. Watson、Richard J.K. Taylor、Norman Lewis

  DOI：10.1016/s0040-4039(00)73870-6

  日期：1993.8

  A short synthesis of the novel antibiotic aranorosin is described which employs a novel hypervalent iodine-mediated oxidative hydroxylation of a tyrosinal derivative in the key step. A similar procedure was employed to prepare 6′-epiaranorosin, and hence establish the stereochemistry of the natural compound.

  描述了新型抗生素阿糖胞苷的简短合成，其在关键步骤中采用了新的高价碘介导的酪氨酸衍生物的氧化羟基化作用。采用类似的方法制备6'-表皮阿拉伯糖球蛋白，因此建立了天然化合物的立体化学。
• Isolation and total synthesis of gymnastatin N, a POLO-like kinase 1 active constituent from the fungus Arachniotus punctatus
  作者：Chee Wee Phoon、Brinda Somanadhan、Sabrina Cher Hui Heng、Anna Ngo、Siew Bee Ng、Mark S. Butler、Antony D. Buss、Mui Mui Sim

  DOI：10.1016/j.tet.2004.09.046

  日期：2004.12

  as a minor component. Gymnastatin N (1) was found to be a 52:48 mixture of (1S,6′R) and (1R,6′R) diastereomers, by synthesis of the four possible diastereomers and comparison of the optical rotation and chiral HPLC profile of each diastereoisomer with the natural product. Analogues of 1 were synthesized and evaluated against the Plk1 assay and these SAR studies suggested that the diene and free carboxylic

  针对POLO样激酶1（Plk1）（一种抗癌靶标）的高通量筛选，鉴定了一种来自点状真菌Arachniotus punctatus的活性提取物。生物测定指导的分馏导致分离出新的天然产物gymaststatin N（1）和已知的化合物阿诺洛糖醇A（2），IC 50值分别为13和118μM 。分离出金格他汀N，3的12'-羟基类似物作为次要成分。Gymnastatin N（1）被认为是（1的52:48混合物小号，6' - [R ）和（1 - [R，6' - [R）非对映异构体，可以合成四种可能的非对映异构体，并比较每种非对映异构体与天然产物的旋光度和手性HPLC谱。合成了类似物1并针对Plk1分析进行了评估，这些SAR研究表明，二烯和游离羧酸部分可能是其生物活性的原因。
• Total Synthesis and Structural Reassignment of Aranorosinol A, Aranorosinol B, and EI-2128-1
  作者：Haiyong Yu、Yingyuan Tian、Yan Zong、Jianyu Zhang、Tao Xu

  DOI：10.1021/acs.joc.0c00028

  日期：2020.3.20

  Herein, we report a concise and collective total synthesis of three natural products: aranorosinol A, aranorosinol B, EI-2128-1 and also the known penicimutanolone. A unified strategy was conceived that divergently accessed all four congeners within 9~11 steps (LLS) from a common intermediate. A bisoxirane-directed 1,2-addition was utilized as a key step to generate the desired configuration of the

  在本文中，我们报告了三种天然产物的简明和集体全合成：阿诺洛糖醇A，阿诺洛糖醇B，EI-2128-1以及已知的青霉烷酮。构想出一种统一的策略，可以从一个公共中间体以9到11个步骤（LLS）内的不同方式访问所有四个同类对象。将双环氧乙烷定向的1，2-加成用作关键步骤，以生成所需的阿拉诺诺醇A和B的C8立体中心构型，在首次分离26年后，它们均被指定为S构型，而C4'和C EI-2128-1的C6'构型均被确定为R，R构型。
• Total Synthesis of a Novel Cytotoxic Metabolite Gymnastatin A
  作者：Mukund K. Gurjar、Pushpal Bhaket

  DOI：10.3987/com-99-8745

  日期：——
• Total synthesis and structure assignment of the antitumor antibiotic aranorosin
  作者：Peter Wipf、Yuntae Kim、Paul C. Fritch

  DOI：10.1021/jo00077a050

  日期：1993.12

  The structurally unique antifungal and antitumor antibiotic aranorosin was prepared in a convergent, stereoselective sequence. Oxidative cyclization of N-protected L-tyrosine, followed by face-selective 1,2-addition of [(benzyloxy)methyl]lithium, Henbest oxidation in the presence of Kishi's radical inhibitor, and simultaneous N,O-deprotection led to an amino diol which was N-acylated with the fatty acid side-chain segment. After a low-temperature reduction of the lactone moiety to the lactol, the carbonyl function was regenerated under neutral conditions by diol cleavage with sodium periodate. Preparation of the acid side chain involved a diastereoselective imide alpha-alkylation directed by Evans' oxazolidinone auxiliary, followed by a series of Wittig-Horner chain extensions. Since the relative configuration at the C (6') position of the natural product had not been determined, we prepared both the (6'S) and the (6'R) isomers of aranorosin. Comparison of synthetic material with the reported spectral data for natural (-)-aranorosin, especially H-1 and C-13 NMR and [alpha]D, did not allow a definitive assignment. After purification of a sample of the isolated material from Pseudoarachniotus roseus, the corrected [alpha]D strongly indicated the (6'R)-stereochemistry for the natural compound. This assignment was confirmed by circular dichroism spectra for (6'S)- and (6'R)-aranorosin and the natural material.