1,2-cyclohexylidenedioxybut-3-yne | 131606-81-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-cyclohexylidenedioxybut-3-yne
• 英文别名: (R)-1,2-cyclohexylidenedioxybut-3-yne；(2R)-2-ethynyl-1,4-dioxaspiro[4.5]decane；(2R)-1,2-cyclohexylidenedioxybut-3-yne；(3R)-3-ethynyl-1,4-dioxaspiro[4.5]decane
• CAS: 131606-81-0
• 化学式: C₁₀H₁₄O₂
• 分子量: 166.22
• InChiKey: FHHMEKXWEIFKKR-SECBINFHSA-N

物化性质

• 沸点：
  233.5±35.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2-cyclohexylidenedioxybut-3-yne 在 正丁基锂 、 碘 作用下， 以 四氢呋喃 为溶剂， 以99%的产率得到(R)-2-Iodoethynyl-1,4-dioxa-spiro[4.5]decane
  参考文献：
  名称：

  呋喃木脂素 (+)-芝麻素和 (-)-细辛素的非对映发散手性合成

  摘要：

  两种非对映体木酚素 (+)-芝麻素和 (-)-asarin 已通过手性 Heck 反应生成的常见中间体非对映发散地制备。

  DOI：

  10.1246/cl.1995.543
• 作为产物：
  描述：

  L-门冬酰-L-苯基丙氨酰-L-苯基丙氨酰-L-缬氨酰甘氨酰-L-亮氨酰-L-蛋氨酸 在 sodium periodate 、 lithium aluminium tetrahydride 、 正丁基锂 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.33h， 生成 1,2-cyclohexylidenedioxybut-3-yne
  参考文献：
  名称：

  First Total Synthesis of Symbioramide, a Novel Ca²⁺-ATPase Activator fromSymbiodiniumsp.

  摘要：

  描述了symbioramide (1) 的首次全合成，并同时确定了1的完整立体结构为(2S,3R,2′R,3′E)-N-(2′-羟基-3′-十八烯酰)-二氢鞘氨醇。

  DOI：

  10.1246/cl.1990.1407

文献信息

• Enantioselective total synthesis of callipeltoside A: two approaches to the macrolactone fragment
  作者：David A. Evans、Jason D. Burch、Essa Hu、Georg Jaeschke

  DOI：10.1016/j.tet.2008.02.001

  日期：2008.5

  The enantioselective total synthesis of callipeltoside A is described. Two syntheses of the macrolactone subunit are included: the first relies upon an Ireland-Claisen rearrangement to generate the trisubstituted olefin geometry and the second utilizes an enantioselective vinylogous aldol reaction for this purpose. Enantioselective syntheses of the sugar and chlorocyclopropane side chain fragments

  描述了 callipeltoside A 的对映选择性全合成。包括大环内酯亚基的两种合成：第一种依赖于爱尔兰-克莱森重排来产生三取代的烯烃几何结构，第二种利用对映选择性插烯羟醛反应来实现此目的。还公开了糖和氯代环丙烷侧链片段的对映选择性合成。该天然产物的相对和绝对立体化学通过与侧链片段的两种对映异构体的片段偶联来确定。
• An Efficient Synthesis of Optically Active [4-13C] Labelled Quorum Sensing Signal Autoinducer-2
  作者：Osvaldo S. Ascenso、Gonzalo Carrau、Karina B. Xavier、M. Rita Ventura、Christopher D. Maycock

  DOI：10.3390/molecules26020369

  日期：——

  [1-13C]-bromoacetic acid. The key step in this process was the enantioselective reduction of an intermediate ketone. This synthesis provides, selectively, both enantiomers of the labelled or unlabelled parent compound, (R) or (S)-4,5-dihydroxypentane-2,3-dione (DPD) and was used for an improved synthesis of [1-13C]-AI-2.

  描述了群体感应信号 Autoinducer-2 (AI-2) 的新合成路线，并用于从 [1-13C]-溴乙酸开始制备 [4-13C]-AI-2。该过程的关键步骤是中间体酮的对映选择性还原。该合成选择性地提供标记或未标记母体化合物 (R) 或 (S)-4,5-二羟基戊烷-2,3-二酮 (DPD) 的两种对映异构体，并用于改进 [1-13C ]-AI-2。
• [EN] EXPEDITIOUS SYNTHESIS OF DPD<br/>[FR] SYNTHESE RAPIDE DE DPD
  申请人：UNIV PRINCETON

  公开号：WO2006034269A1

  公开（公告）日：2006-03-30

  This invention provides a practical synthesis route for 4,5-dihydroxypentane-2,3-dione (DPD), an unstable small molecule which is proposed to be the source of universal signaling agents for quorum sensing in bacteria. The synthesis route includes new intermediates and allows preparation of isotopically-labeled DPD and ent-DPD. The method provides sufficient quantities of DPD for study of spontaneous binding of borate to DPD, the signal for the marine bacteria V. harveyi

  这项发明提供了一种实用的合成途径，用于合成4,5-二羟基戊烷-2,3-二酮（DPD），这是一种不稳定的小分子，被认为是细菌群体感应通用信号物质的来源。该合成途径包括新的中间体，并允许制备同位素标记的DPD和ent-DPD。该方法提供了足够数量的DPD，以研究硼酸与DPD的自发结合，这是海洋细菌V. harveyi的信号。
• Synthetic studies of callyspongiolide: synthesis of the macrolactone core of the molecule
  作者：Sudhakar Athe、Ashish Sharma、Kanakaraju Marumudi、Subhash Ghosh

  DOI：10.1039/c6ob01007e

  日期：——

  strategy has been developed for the synthesis of the macrolactone core 2 of a unique polyketide callyspongiolide 1. The key features of the strategy included an Evan's asymmetric alkylation, diastereoselective Michael type alkylation, Brown's asymmetric allylation reaction, an allylic alkylation of an activated Z-allylic alcohol and an intramolecular Z-selective intramolecular H–W–E olefination.

  已开发出一种简明的合成策略，用于合成独特的聚酮化合物Callyspongiolide 1的大内酯核2。该策略的主要特征包括埃文（Evan）不对称烷基化，非对映选择性Michael型烷基化，布朗（Brown）不对称烯丙基化反应，活化的Z-烯丙基醇的烯丙基烷基化和分子内Z-选择性分子内H–W–E烯化反应。
• An Unexpected Switch in the Modulation of AI-2-Based Quorum Sensing Discovered through Synthetic 4,5-Dihydroxy-2,3-pentanedione Analogues
  作者：Colin A. Lowery、Junguk Park、Gunnar F. Kaufmann、Kim D. Janda

  DOI：10.1021/ja802353j

  日期：2008.7.1

  Quorum sensing (QS) has traditionally referred to a mechanism of communication within a species of bacteria. However, emerging research implicates QS in interspecies communication and competition, and such systems have been proposed in a wide variety of bacteria, The AI-2-based QS system represents the most studied of these proposed interspecies systems, and has been proposed to regulate diverse functions such as bioluminescence, expression of virulence factors, and biofilm formation. As such, the development of modulatory compounds, both agonists and antagonists, is of great interest for the treatment of bacterial infections and the study of unknown AI-2-based QS systems. Toward this end, we have designed and synthesized a panel of 4,5-dihydroxy-2,3-pentanedione/AI-2 analogues and evaluated their effects on the AI-2 QS of various bacteria. The panel of compounds exhibited differential effects in the bacterial cell lines examined, providing a platform for the development of broad-spectrum modulators of AI-2-based QS.