(S)-2,5-dimethylhex-4-enal | 218924-92-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-2,5-dimethylhex-4-enal
• 英文别名: (S)-5,5-dimethyl-4-pentenal；2,5-dimethyl-4-hexenal；(s)-2,5-Dimethylhex-4-enal；(2S)-2,5-dimethylhex-4-enal
• CAS: 218924-92-6
• 化学式: C₈H₁₄O
• 分子量: 126.199
• InChiKey: NTPNJYFKMSTHQR-QMMMGPOBSA-N

物化性质

• 沸点：
  167.0±9.0 °C(Predicted)
• 密度：
  0.831±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-2,5-dimethylhex-4-enal 在 戴斯-马丁氧化剂 、 magnesium 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 (S)-4,7-dimethyl-6-octen-3-one
  参考文献：
  名称：

  Syntheses and odor properties of optically active dimethyl octenone and its analogs

  摘要：

  The optically active isomers of dimethyl octenone, which is used in citrus accords, and its analogs, were synthesized from a common chiral intermediate prepared by the lipase-catalyzed desymmetrization of prochiral diol. The results of an olfactory evaluation of the prepared isomers are also reported. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.02.002
• 作为产物：
  描述：

  (3-甲基丁-2-烯基)丙二酸二乙酯 在 吡啶 、 lithium aluminium tetrahydride 、 Amano PS Lipase 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 异丙醚 为溶剂， 反应 9.0h， 生成 (S)-2,5-dimethylhex-4-enal
  参考文献：
  名称：

  Syntheses and odor properties of optically active dimethyl octenone and its analogs

  摘要：

  The optically active isomers of dimethyl octenone, which is used in citrus accords, and its analogs, were synthesized from a common chiral intermediate prepared by the lipase-catalyzed desymmetrization of prochiral diol. The results of an olfactory evaluation of the prepared isomers are also reported. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.02.002

文献信息

• Thermal proteome profiling efficiently identifies ribosome destabilizing oxazolidinones
  作者：Christina Nöcker、Nadine Kaiser、Daniel Foley、Sonja Sievers、Petra Janning、Herbert Waldmann、Luca Laraia

  DOI：10.1016/j.tet.2021.132118

  日期：2021.5

  Identifying the targets of bioactive small molecules is a challenging endeavor for which no general solution currently exists. Classical affinity purification experiments suffer from the need to functionalise a bioactive compound and link it to a solid support, which may interfere with target binding. A modern mass spectrometry-based proteomics technique that has partially circumvented this problem

  鉴定具有生物活性的小分子的靶标是一项具有挑战性的工作，目前尚无通用的解决方案。经典的亲和纯化实验需要功能化生物活性化合物并将其连接到固体支持物上，这可能会干扰靶标结合。基于现代质谱的蛋白质组学技术已部分规避了此问题，是热蛋白质组分析（TPP），它同时确定了未修饰的小分子对整个蛋白质组的热稳定性的影响。在这里，我们使用TPP来识别基于经常用作手性助剂的恶唑烷酮的新发现的自噬抑制剂的作用方式。出乎意料的是，发现所有核糖体蛋白中有很大一部分被抑制剂破坏了稳定性，
• ——
  作者：Claudia M. Schulz、Lutz Lehmann、Rumsaïs Blatrix、Pierre Jaisson、Abraham Hefetz、Wittko Francke

  DOI：10.1023/a:1021492204400

  日期：——

  Extracts of Dufour's gland of the ponerine ant, Gnamptogenys striatula, were analyzed by using the combination of gas chromatography and mass spectrometry. Series of esters of the new homoterpenoids (2E,6)-3,4,7-trimethyl-2,6-octadiene-1-ol (4-methylgeraniol) and (2E,6)-3,4,7-trimethyl-2,6-nonadiene-1-ol (bishomogeraniol) with unbranched medium-chain fatty acids were identified. Transformation of the

  通过使用气相色谱法和质谱法相结合的方法对杜弗氏蚂蚁腺体Gnamptogenys striatula的提取物进行了分析。新的类萜类化合物（2E，6）-3,4,7-三甲基-2,6-辛二烯-1-醇（4-甲基香叶醇）和（2E，6）-3,4,7-三甲基-鉴定了具有直链中链脂肪酸的2，6-壬二烯-1-醇（双香叶香叶醇）。手性天然产物向1,4-二（三氟乙酰氧基）-3-甲基戊烷的转化以及在修饰的环糊精相上的气相色谱保留时间与合成旋光参考样品的气相色谱保留时间的比较证明，立体中心可以保持（S）-组态。萃取物中的（2E，4S，6）-3,4,7-三甲基-2,6-辛二烯-1-基酯和相应的十二烷酸酯是主要的挥发物。
• A Novel Aldol Condensation with 2-Methyl-4-pentenal and Its Application to an Improved Total Synthesis of Epothilone B
  作者：Aaron Balog、Christina Harris、Kenneth Savin、Xiu-Guo Zhang、Ting-Chao Chou、Samuel J. Danishefsky

  DOI：10.1002/(sici)1521-3773(19981016)37:19<2675::aid-anie2675>3.0.co;2-o

  日期：1998.10.16

  responsible for the high diastereoface selectivity of the aldol reaction. This key step in the highly concise total synthesis of epothilone B is followed by a Suzuki coupling to introduce the thiazole domain, a Noyori reduction to control the stereochemistry at C3, and a final macrolactonization (see reaction scheme). X=protecting group.

  通过1的双键和2的羰基之间的良好相互作用来稳定过渡态似乎是醛醇缩醛反应的高非对映体选择性的原因。高度精确的埃博霉素B合成的关键步骤是进行铃木偶联以引入噻唑结构域，Noyori还原以控制C3的立体化学，以及最终的大内酯化（参见反应方案）。X ＝保护基。
• New Chemical Synthesis of the Promising Cancer Chemotherapeutic Agent 12,13-Desoxyepothilone B: Discovery of a Surprising Long-Range Effect on the Diastereoselectivity of an Aldol Condensation
  作者：Christina R. Harris、Scott D. Kuduk、Aaron Balog、Ken Savin、Peter W. Glunz、Samuel J. Danishefsky

  DOI：10.1021/ja991189l

  日期：1999.8.1

  The epothilones are naturally occurring cytotoxic molecules that possess the remarkable ability to arrest cell division through the stabilization of microtubule assemblies. Our in vivo studies with 12,13-desoxyepothilone B (dEpoB), have established that the desoxy compound is well tolerated and virtually curative against a variety of sensitive and resistant xenograft tumors in animal models. In light of these discoveries, we sought a chemical synthesis of dEpoB that would be able to support a serious and substantial discovery research program directed toward the clinical development of this molecule. The overall strategy for this endeavor assumed the ability to synthesize dEpoB from three constructs which include an achiral beta,delta-diketo ester construct A, an (S)-2-methylpentenal moiety B, and the thiazoyl-containing vinyl iodide moiety C. We envisioned that a diastereoselective aldol condensation between an achiral C5-C6 (Z)-metalloenolate derived from construct A and an (S)-2-methylalkanal fragment, B, would generate the desired C6-C7 bond. Second, a B-alkyl Suzuki coupling between the vinyl iodide construct C and an alkyl borane would form the C11-C12 bond. Finally, a late-stage reduction of the C3 ketone to the requisite C3 alcohol with high asymmetric induction would permit us to introduce the beta,delta-diketo ester fragment A, into the synthesis as a readily accessible achiral building block. The governing concepts for our new synthesis are described herein.