辛-7-烯-4-炔-1-醇 | 160812-22-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 辛-7-烯-4-炔-1-醇
• 英文名称: oct-7-en-4-yn-1-ol
• CAS: 160812-22-6
• 化学式: C₈H₁₂O
• 分子量: 124.183
• InChiKey: LIOAFCWLPFAZHO-UHFFFAOYSA-N

物化性质

• 沸点：
  179.5±23.0 °C(Predicted)
• 密度：
  0.909±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  辛-7-烯-4-炔-1-醇 在 Jones reagent 作用下， 以 丙酮 为溶剂， 以69%的产率得到oct-7-en-4-ynoic acid
  参考文献：
  名称：

  Total synthesis of the macrophage derived anti-inflammatory lipid mediator Maresin 1

  摘要：

  The total synthesis of Maresin 1, an endogenous macrophage pro-resolving lipid mediator derived from docosahexaenoic acid, has been achieved. The chiral hydroxy-group at C7 was obtained via a Jacobsen hydrolytic kinetic resolution of a terminal epoxide whereas the center at C14 arises from a chiral pool strategy starting from 2-deoxy-D-ribose. Pd-0/Cu-1 Sonogashira coupling of the two key fragments and 2n(Cu/Ag) reduction completed the total synthesis of Maresin 1. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.05.143
• 作为产物：
  描述：

  4-戊炔-1-醇 、 3-溴丙烯 在 四丁基氯化铵 、 potassium carbonate 、 copper(l) chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以90%的产率得到辛-7-烯-4-炔-1-醇
  参考文献：
  名称：

  氯化铜（I）/ 2,2'-联吡啶催化的二氯和三氯乙酸酯的环化反应合成中型内酯

  摘要：

  中性内酯（8至11元环）是通过Cu（bpy）Cl在1,2-二氯乙烷或苯中的80-190°C温度下催化各种烯基二-和三氯乙酸酯的环化反应有效形成的。最好将烯烃加成反应的机理理解为通过自由基型中间体进行的氯原子转移过程。独家内-cyclization在所有病例中观察到。十元和十一元内酯只能通过“刚性链”方法访问，在该方法中，炔烃或烯烃官能团被纳入连接反应中心的链中，从而降低了分子的柔韧性。

  DOI：

  10.1016/s0040-4020(01)89549-1

文献信息

• 4-Hydroxy-6-alkyl-2-pyrones as nucleophilic coupling partners in Mitsunobu reactions and oxa-Michael additions
  作者：Michael J Burns、Thomas O Ronson、Richard J K Taylor、Ian J S Fairlamb

  DOI：10.3762/bjoc.10.116

  日期：——

  Two mild and efficient strategies have been developed for the O-functionalisation of 4-hydroxy-6-alkyl-2-pyrones, by using them as nucleophilic partners in oxa-Michael additions and the Mitsunobu reaction. The reactions proceed in moderate to excellent yields on a range of substrates containing useful functionality. The reactions serve as practical and valuable synthetic methods to construct complex 2-pyronyl ethers, which are found embedded in a number of natural products.

  已开发了两种温和高效的策略，用于将4-羟基-6-烷基-2-吡喃烯氧化功能化，通过将它们用作氧杂Michael加成和三冈反应中的亲核试剂。这些反应在包含有用官能团的一系列底物上以中等至优良的产率进行。这些反应作为实用且有价值的合成方法，用于构建复杂的2-吡喃醚，这些醚嵌入在许多天然产物中。
• Copper(I)-Catalyzed Enantioselective Addition of Enynes to Ketones
  作者：Xiao-Feng Wei、Xiao-Wei Xie、Yohei Shimizu、Motomu Kanai

  DOI：10.1021/jacs.7b01254

  日期：2017.4.5

  A copper(I)-catalyzed enantioselective addition of enynes to ketones was developed. The method allows facile construction of enantiomerically enriched tertiary alcohols using skipped enynes as stable hydrocarbon pronucleophiles. The combination of a soft copper(I)-conjugated Brønsted base catalyst with a chiral diphosphine ligand, (S,S)-Ph-BPE, enabled chemoselective deprotonation of the skipped enynes

  开发了铜（I）催化的烯炔与酮的对映选择性加成。该方法允许使用跳过的烯炔作为稳定的烃亲核试剂轻松构建对映异构体富集的叔醇。软铜 (I)-共轭 Brønsted 碱催化剂与手性二膦配体 (S,S)-Ph-BPE 的组合，能够在带有本质上更具酸性的 α-质子的酮的存在下对跳过的烯炔进行化学选择性去质子化。催化生成的手性烯丙基铜物种对映-、非对映-、区域-和化学选择性与酮反应，从而表现出优异的底物通用性和官能团耐受性。亲核试剂的跳过的烯炔部分专门转化为顺式共轭烯炔，
• Palladium/Norbornene-Catalyzed C−H Alkylation/Alkyne Insertion/Indole Dearomatization Domino Reaction: Assembly of Spiroindolenine-Containing Pentacyclic Frameworks
  作者：Lu Bai、Jingjing Liu、Wenjie Hu、Kunyu Li、Yaoyu Wang、Xinjun Luan

  DOI：10.1002/anie.201801894

  日期：2018.4.23

  indole‐based biaryls with bromoalkyl alkynes by using palladium/norbornene (Pd/NBE) cooperative catalysis. This reaction is realized through a sequence of Catellani‐type C−H alkylation, alkyne insertion, and indole dearomatization, by forming two C(sp2)−C(sp3) and one C(sp2)−C(sp2) bonds in a single chemical operation, thus providing a diverse range of pentacyclic molecules, containing a spiroindolenine fragment

  据报道，通过使用钯/降冰片烯（Pd / NBE）协同催化，吲哚基联芳基与溴代烷基炔烃具有高度化学选择性的分子间环化。通过形成两个C（sp 2）-C（sp 3）和一个C（sp 2）-C（sp 2）来实现一系列Catellani型CH烷基化，炔烃插入和吲哚脱芳香化反应）在一个化学操作中键合，从而以良好的收率和优异的官能团耐受性提供了多种范围的包含螺环吲哚片段的五环分子。初步的机理研究表明，速率决定步骤中可能涉及到CH键的断裂，并且吲哚脱芳香化作用可能是通过烯烃配位/插入和β-氢化物消除的Heck型途径进行的。
• Synthesis of 2-Pyridones by Cycloreversion of [2.2.2]- Bicycloalkene Diketopiperazines
  作者：Kaila A. Margrey、Amy D. Hazzard、Jonathan R. Scheerer

  DOI：10.1021/ol403632t

  日期：2014.2.7

  5-diketopiperazine (DKP) derivatives, is compatible with both aromatic and aliphatic aldehyde components, and can intercept either intra- or intermolecular cycloaddition manifolds. Priming of one aza-bridging function in the intermediate [2.2.2]-DKP scaffold permits cycloreversion (microwave heating) and selective extrusion of cyanate derivatives leading to the formation of 2-pyridone structures. Progress

  报道了将[2.2.2]-二氮杂双环烯烃结构转化为2-吡啶酮芳族杂环产物的一般策略。反应顺序从2,5-二酮哌嗪（DKP）衍生物开始，与芳香族和脂肪族醛组分均相容，并且可以拦截分子内或分子间的环加成歧管。在中间[2.2.2] -DKP支架中引发一种氮杂桥键功能可实现环还原（微波加热）和选择性挤压氰酸酯衍生物，从而导致2-吡啶酮结构的形成。还公开了路易宁A和B，即抗增殖的2-吡啶酮天然产物的合成进展。
• Discovery, Synthetic Methodology, and Biological Evaluation for Antiphotoaging Activity of Bicyclic[1,2,3]triazoles: In Vitro and in Vivo Studies
  作者：Hsin-Yu Hsieh、Wen-Chun Lee、Gopal Chandru Senadi、Wan-Ping Hu、Jium-Jia Liang、Tong-Rong Tsai、Yu-Wei Chou、Kung-Kai Kuo、Chung-Yu Chen、Jeh-Jeng Wang

  DOI：10.1021/jm400394s

  日期：2013.7.11

  Novel bicyclic[1,2,3]triazoles (4, 7, 11, 15) have been synthesized using a one-pot metal free strategy with high structural diversity as photoprotective agents, and their effect on UVA-induced senescence in human dermal fibroblast cells (FB) and the associated mechanism are delineated. lid plus UVA can induce a decrease in reactive oxygen species (ROS) production and senescence-associated beta-galactosiclase (SA-beta-gal) activity but an increase in adenosine triphosphate (ATP) synthesis and mitochondrial membrane potential (Delta psi(mt)). The mRNA levels of six senescence-associated genes, matrix metalloproteinase-1 (MMP-1), was decreased, while elastin, procollagen I type I, fibronectin, COL1 alpha 1, and tissue inhibitor of metalloproteinase-1 (TIMP-1) were increased. lid plus UVA also decreased MMP-1 and increased TIMP-1 protein levels. Additionally, the thickness of the minim dorsal skin and epidermis, by UVA, was decreased by topical lid treatment. Our results indicate that bicyclic[1,2,3]triazoles protect UVA-induced senescence-like characteristics in FB cells, which may provide potential prevention against photoaging.