(2E,4E,6S,7S,8R,9S,10E)-7,9-dimethoxy-3,6,8-trimethyl-11-phenylundeca-2,4,10-trienamide | 237425-38-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2E,4E,6S,7S,8R,9S,10E)-7,9-dimethoxy-3,6,8-trimethyl-11-phenylundeca-2,4,10-trienamide
• 英文别名: 7,9-dimethoxy-3,6,8-trimethyl-11-phenyl-(2E,4E,6S,7S,8R,9S,10E)-2,4,10-undecatrienamide；(+)-crocacin C；crocacin C
• CAS: 237425-38-6
• 化学式: C₂₂H₃₁NO₃
• 分子量: 357.493
• InChiKey: JCMQQWWEDGWMJB-ZAFMVVCLSA-N

物化性质

• 熔点：
  87-88 °C
• 沸点：
  532.1±50.0 °C(Predicted)
• 密度：
  1.030±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2E,4E,6S,7S,8R,9S,10E)-7,9-dimethoxy-3,6,8-trimethyl-11-phenylundeca-2,4,10-trienamide 、 (Z)-methyl 2-(6-iodohex-5-enamido)acetate 在 copper(l) iodide 、 caesium carbonate 、 N,N'-二甲基乙二胺 作用下， 以 四氢呋喃 为溶剂， 生成 methyl 2-((Z)-6-((2E,4E,6S,7S,8R,9S,10E)-7,9-dimethoxy-3,6,8-trimethyl-11-phenylundeca-2,4,10-trienamido)hex-5-enamido)acetate
  参考文献：
  名称：

  Synthesis of (+)-crocacin D and simplified bioactive analogues

  摘要：

  The total synthesis of (+)-crocacin D has been achieved in 15 steps (9 isolated intermediates) and 14% overall yield from commercially available starting materials and using (+)-crocacin C as a key intermediate. A number of simplified analogues and their biological activities are also reported. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.01.008
• 作为产物：
  描述：

  (4R,5S)-3-<(2R,3R,4E)-3-Hydroxy-2-methyl-5-phenyl-4-pentenoyl>-4-methyl-5-phenyl-2-oxazolidinone 在 三甲基铝 、 sodium hydride 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 34.0h， 生成 (2E,4E,6S,7S,8R,9S,10E)-7,9-dimethoxy-3,6,8-trimethyl-11-phenylundeca-2,4,10-trienamide
  参考文献：
  名称：

  Enantioselective Synthesis of (+)-Crocacin C. An Example of a Highly Challenging Mismatched Double Asymmetric δ-Stannylcrotylboration Reaction

  摘要：

  A concise, enantioselective synthesis of (+)-crocacin C is described, featuring a highly diastereoselective mismatched double asymmetric delta-stannylcrotylboration of the stereochemically demanding chiral aldehyde 9 with the bifunctional crotylborane reagent (S)-E-10. The total synthesis of (+)-crocacin C was accomplished in seven steps (longest linear sequence) starting from commercially available precursors.

  DOI：

  10.1021/ol300476f

文献信息

• [EN] APPARATUS AND METHODS FOR THE AUTOMATED SYNTHESIS OF SMALL MOLECULES<br/>[FR] APPAREIL ET PROCÉDÉS POUR LA SYNTHÈSE AUTOMATISÉE DE PETITES MOLÉCULES
  申请人：UNIV ILLINOIS

  公开号：WO2012012756A1

  公开（公告）日：2012-01-26

  Provided are methods for purifying N-methyliminodiacetic acid (MID A) boronates from solution. Also provided are methods for deprotection of boronic acids from their MIDA ligands. The purification and deprotection methods can be used in conjunction with methods for coupling or otherwise reacting boronic acids. Iterative cycles of deprotection, coupling, and purification can be performed to synthesize chemical compounds of interest. The methods are suitable for use in an automated chemical synthesis process. Also provided is an automated small molecule synthesizer apparatus for performing automated synthesis of small molecules using iterative cycles of deprotection, coupling, and purification in accordance with methods of the invention. Coupling and other reactions embraced by the invention include, without limitation, Suzuki-Miyaura coupling, oxidation, Swern oxidation, "Jones reagents" oxidation, reduction, Evans' aldol reaction, HWE olefmation, Takai olefmation, alcohol silylation, desilylation, /?-methoxybenzylation, iodination, Negishi cross-coupling, Heck coupling, Miyaura borylation, Stille coupling, and Sonogashira coupling.

  提供了从溶液中纯化N-甲基亚胺二乙酸（MID A）硼酸酯的方法。还提供了一种从其MIDA配体中去保护硼酸的方法。这些纯化和去保护方法可以与硼酸的偶联或其他反应方法结合使用。可以进行去保护、偶联和纯化的迭代循环，以合成感兴趣的化合物。这些方法适用于自动化化学合成过程。还提供了一种用于根据本发明方法执行去保护、偶联和纯化迭代循环的自动化小分子合成器装置。本发明涵盖的偶联和其他反应包括但不限于Suzuki-Miyaura偶联、氧化、Swern氧化、"Jones试剂"氧化、还原、Evans的Aldol反应、HWE烯烃化、Takai烯烃化、醇硅基化、去硅基化、/β-甲氧基苄化、碘化、Negishi交叉偶联、Heck偶联、Miyaura硼化、Stille偶联和Sonogashira偶联。
• Total Synthesis of (+)-Crocacin D
  作者：Luiz C. Dias、Luciana G. de Oliveira、Janaína D. Vilcachagua、Florian Nigsch

  DOI：10.1021/jo047732k

  日期：2005.3.1

  The total synthesis of (+)-crocacin D is described. The convergent asymmetric synthesis relies on the use of a Stille cross-coupling between an (E)-vinyl stannane with an (E)-vinyl iodide to establish the (E,E)-dienamide moiety followed by a mild and efficient copper-catalyzed coupling between (+)-crocacin C and a (Z)-vinyl iodide to establish the challenging (Z)-enamide function.
• Total synthesis of (+)-crocacin C
  作者：Gopal Sirasani、Tapas Paul、Rodrigo B. Andrade

  DOI：10.1016/j.bmc.2010.03.003

  日期：2010.6.1

  Two approaches toward the total synthesis of cytotoxic polyketide natural product (+)-crocacin C (1) are described. The first approach, which was ultimately unsuccessful, was replaced altogether with a second that afforded target 1 in 10 linear steps from commercially available Evans' chiral propionimide (5% overall yield). No protecting groups were utilized in the total synthesis of 1. (C) 2010 Elsevier Ltd. All rights reserved.
• Concise Total Synthesis of (+)-Crocacin C
  作者：Gopal Sirasani、Tapas Paul、Rodrigo B. Andrade

  DOI：10.1021/jo800906p

  日期：2008.8.1

  [GRAPHICS]The cytotoxic natural product (+)-crocacin C (1) has been synthesized in 10 linear steps from commercially available Evans' chiral propionimide. in 5% overall yield (8 steps from Evans' chiral dipropionate synthon). No protecting groups were utilized.
• Step-Economic Synthesis of (+)-Crocacin C: A Concise Crotylboronation/[3,3]-Sigmatropic Rearrangement Approach
  作者：Adele E. Pasqua、Frank D. Ferrari、Chris Hamman、Yanzhou Liu、James J. Crawford、Rodolfo Marquez

  DOI：10.1021/jo301210f

  日期：2012.8.17

  The step-economic total synthesis of (+)-crocacin C has been achieved in 20% yield from commercially available starting materials. This approach requires the isolation of only 8 intermediates and can provide a reliable supply of (+)-crocacin C for the development of new antifungal and crop protection agents.