(1E)(3R)-2-methyl-1-[2-methyl(1,3-thiazol-4-yl)]hexa-1,5-dien-3-ol | 198571-81-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (1E)(3R)-2-methyl-1-[2-methyl(1,3-thiazol-4-yl)]hexa-1,5-dien-3-ol
• 英文别名: (R)-2-methyl-4-([1E]-2'-methylhexa-1',5'-dien-3'-ol)thiazole；(R,E)-2-methyl-1-(2-methylthiazol-4-yl)hexa-1,5-dien-3-ol；(1E,3R)-2-methyl-1-(2-methyl-1,3-thiazol-4-yl)hexa-1,5-dien-3-ol
• CAS: 198571-81-2
• 化学式: C₁₁H₁₅NOS
• 分子量: 209.312
• InChiKey: SAMXUQPRBXCGFQ-LXSSAFMLSA-N

物化性质

• 沸点：
  353.5±30.0 °C(Predicted)
• 密度：
  1.112±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  61.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1E)(3R)-2-methyl-1-[2-methyl(1,3-thiazol-4-yl)]hexa-1,5-dien-3-ol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 4-二甲氨基吡啶 、 2,4,6-三氯苯甲酰氯 、 四丁基氟化铵 、 溶剂黄146 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 89.0h， 生成 (4S,7E,9R,10S,13E,16R)-9-hydroxy-4,10-dimethyl-16-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1,5,11-trioxacyclohexadeca-7,13-diene-2,6,12-trione
  参考文献：
  名称：

  Synthesis of Macrosphelides with a Thiazole Side Chain:  New Antitumor Candidates Having Apoptosis-Inducing Property

  摘要：

  Hybrid compounds of macrosphelides and epothilones, both of which are natural macrolides having a 16-membered skeleton, were designed and synthesized using a ring-closing metathesis (RCM) strategy. Some of these hybrids were found to exhibit notable apoptosis-inducing activity against human lymphoma cells with higher potency than parent natural macrosphelides, and to be a promising lead compound for development of a new antitumor agent.

  DOI：

  10.1021/ol061922v
• 作为产物：
  描述：

  (R)-2-((2-methylthiazol-4-yl)methyl)hexa-1,5-dien-3-yl acetate 在 potassium tert-butylate 、 水 作用下， 以 叔丁醇 为溶剂， 反应 0.75h， 生成 (1E)(3R)-2-methyl-1-[2-methyl(1,3-thiazol-4-yl)]hexa-1,5-dien-3-ol
  参考文献：
  名称：

  A cyclopropanol approach to the synthesis of both enantiomers of the C13–C21 fragment of epothilones

  摘要：

  Efficient syntheses of both enantiomers of the C13-C21 fragment of epothilone molecules have been performed by use of enantiomeric oxiranyl-substituted cyclopropylsulfonates as key intermediates. The latter were obtained by the cyclopropanation of easily available (R)-methyl 2,3-O-isopropylideneglycerate and subsequent manipulation of the functional groups. Asymmetric allylation of 1-formylcyclopropyl pivalate led to an alternative precursor of the target compounds with moderate enantioselectivity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.02.003

文献信息

• Multi-Step Application of Immobilized Reagents and Scavengers: A Total Synthesis of Epothilone C
  作者：R. Ian Storer、Toshiyasu Takemoto、Philip S. Jackson、Dearg S. Brown、Ian R. Baxendale、Steven V. Ley

  DOI：10.1002/chem.200305669

  日期：2004.5.17

  The total synthesis of the cytotoxic antitumour natural product epothilone C has provided a stage for the exploitation and further development of immobilized reagent methods. A stereoselective convergent synthetic strategy was applied, incorporating polymer-supported reagents, catalysts, scavengers and catch-and-release techniques to avoid frequent aqueous work-up and chromatographic purification.

  细胞毒性抗肿瘤天然产物埃博霉素C的全合成为固定试剂方法的开发和进一步发展提供了一个阶段。应用了立体选择性会聚合成策略，结合了聚合物支持的试剂，催化剂，清除剂和捕集和释放技术，以避免频繁的水后处理和色谱纯化。
• Towards the synthesis of epothilone A: Enantioselective preparation of the thiazole sidechain and macrocyclic ring closure
  作者：Richard E. Taylor、Jeffrey D. Haley

  DOI：10.1016/s0040-4039(97)00285-2

  日期：1997.3

  A synthetic approach to a new class of microtubule-stabilizing natural products is described which employs a macrocyclic olefination strategy to cyclize the 16-membered lactone ring. The C13C19 thiazole subunit of epothilone A and B is prepared in high enantioselectivity using a catalytic asymmetric allylation reaction.

  描述了一种新型的微管稳定天然产物的合成方法，该方法采用大环烯化策略环化16元内酯环。埃博霉素A和B的C13C19噻唑亚基采用催化不对称烯丙基化反应以高对映选择性制备。
• Total Synthesis of Epothilones B and D
  作者：Richard E. Taylor、Yue Chen

  DOI：10.1021/ol010094x

  日期：2001.7.1

  [reaction: see text] A highly convergent total synthesis of the natural products epothilone B and D is described. The route is highlighted by efficient generation of a C12-C13 trisubstituted olefin which exploits a sequential Nozaki-Hiyama-Kishi coupling and a stereoselective thionyl chloride rearrangement.

  [反应：见正文]描述了天然产物埃坡霉素B和D的高度收敛的全合成。有效产生C12-C13三取代的烯烃是该路线的重点，该烯烃利用了连续的Nozaki-Hiyama-Kishi偶联和立体选择性的亚硫酰氯重排。
• Design and synthesis of constrained epothilone analogs: The efficient synthesis of eleven-membered rings by olefin metathesis
  作者：Jeffrey D. Winkler、Joanne M. Holland、Jiri Kasparec、Paul H. Axelsen

  DOI：10.1016/s0040-4020(99)00301-4

  日期：1999.7

  The efficient synthesis of both left- and right-hand halves of a constrained analog of the anticancer natural product epothilone is described. The eleven-membered rings common to both compounds are prepared by olefin metathesis.

  描述了抗癌天然产物埃博霉素的受约束类似物的左半部分和右半部分的有效合成。两种化合物共有的十一元环是通过烯烃复分解制备的。
• Remote Effects in Macrolide Formation through Ring-Forming Olefin Metathesis:  An Application to the Synthesis of Fully Active Epothilone Congeners
  作者：Dongfang Meng、Dai-Shi Su、Aaron Balog、Peter Bertinato、Erik J. Sorensen、Samuel J. Danishefsky、Yu-Huang Zheng、Ting-Chao Chou、Lifeng He、Susan B. Horwitz

  DOI：10.1021/ja964275j

  日期：1997.3.1