(±)-6-methyl-1-heptyn-4-ol | 151908-10-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (±)-6-methyl-1-heptyn-4-ol
• 英文别名: 6-methyl-hept-1-yn-4-ol；6-Methyl-hept-1-in-4-ol；6-Methylhept-1-yn-4-ol
• CAS: 151908-10-0
• 化学式: C₈H₁₄O
• 分子量: 126.199
• InChiKey: CGFMPFSGADAKSD-UHFFFAOYSA-N

物化性质

• 沸点：
  65-70 °C(Press: 13 Torr)
• 密度：
  0.884±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  (±)-6-methyl-1-heptyn-4-ol 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以60.7%的产率得到6-methyl-hept-1-en-4-ol
  参考文献：
  名称：

  β-乙炔末端醇与氢化铝锂的水铝化

  摘要：

  在THF中用氢化锂铝将末端β-乙炔醇加氢，得到均烯丙基醇。用氘化水，碘或二溴化吡啶分解中间有机铝配合物已证明在三键处非区域选择性氢化物的侵蚀。

  DOI：

  10.1134/s1070363216020109
• 作为产物：
  描述：

  3-溴丙炔 、 异戊醛 在 indium 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 生成 (±)-6-methyl-1-heptyn-4-ol
  参考文献：
  名称：

  通过由α-氧代金卡宾产生的氧鎓叶立德的[2,3]-Sigmatropic重排合成2,5-二取代二氢呋喃-3(2H)-酮

  摘要：

  发现了由α-氧代金卡宾产生的氧鎓叶立德的新型 [2,3]-σ 重排。开发了一种有效的 2,5-二取代二氢呋喃-3(2H)-酮的合成方法，通过金催化烯丙基高炔丙基醚与 N-氧化物的分子间氧化。并且通过(±)-kumausallene的简洁形式合成证明了当前方法的合成效用。

  DOI：

  10.1055/s-0033-1339662

文献信息

• A general method for the synthesis of enantiopure aliphatic chain alcohols with established absolute configurations. Part 1. Application of the MαNP acid method to acetylene alcohols
  作者：Yoko Yamamoto、Megumi Akagi、Kumiko Shimanuki、Shunsuke Kuwahara、Masataka Watanabe、Nobuyuki Harada

  DOI：10.1016/j.tetasy.2014.10.007

  日期：2014.11

  applied to various acetylene alcohols 4–12 and 14. In the case of MαNP esters 21b, 24a, and 26a, their absolute configurations were unambiguously determined by X-ray crystallography, which confirmed the absolute configuration assignments performed by 1H NMR anisotropy. These acetylene alcohol MαNP esters can serve as key intermediates for the synthesis of enantiopure aliphatic chain alcohols with established

  使用（A方法小号（+） - - ）2-甲氧基-2-（1-萘基）丙酸1（MαNP酸）已经施加到炔属醇4 - 14由以确定它们的绝对构型1个1 H NMR各向异性和/或X射线晶体学。从外消旋乙炔醇和（非对映体制备酯MαNP小号（+） - - ）MαNP酸1是易于分离的，通过HPLC在硅胶上。从1 1 H NMR各向异性Δ δ分离非对映体MαNP酯Δ数据δ  =  δ（[R ，X） -  δ（小号，X）=  δ（第二FR） -  δ（第一FR）}，第一洗脱酯的绝对构型进行测定。此MαNP酸方法已成功地应用于各种乙炔醇4 - 12和14。在MαNP酯的情况下21B，24A，和26A，它们的绝对构型通过明确地X射线晶体学，这证实所执行的绝对构型确定分配11 H NMR各向异性。这些炔属醇MαNP酯可以如在本系列的第2部分中描述作为对映体纯的脂肪族链醇既定绝对构型的合成的关键中间体。
• Gold(I)-catalysed synthesis of cyclic sulfamidates: current scope, stereochemistry and competing ene-allene cycloisomerisation
  作者：Mari C.M. Higginbotham、Lorna Kennedy、Anita G. Lindsay、Andreas Troester、Magnus W.P. Bebbington

  DOI：10.1016/j.tet.2014.11.058

  日期：2015.1

  Six-membered cyclic sulfamidates are prepared in high yields by treatment of allenic sulfamates with readily available Ph3PAuNTf2. The reaction enables formation of N-substituted quaternary centres in high yields. The relative stereochemistry has been unambiguously determined. A π-rearrangement is faster than hydroamination in the case of an allyl-substituted sulfamate and a mechanism is proposed for

  通过用容易获得的Ph 3 PAuNTf 2处理烯丙基氨基磺酸盐，可以高收率制备六元环状氨基磺酸盐。该反应能够以高收率形成N-取代的季中心。相对立体化学已经明确确定。在烯丙基取代的氨基磺酸酯的情况下，π重排比氢化氨基化更快，并且提出了用于该方法的机理。
• Gold(III) catalyzed stereoselective synthesis of dialkyl dihydrofuran acetates
  作者：Sagarika Behera、Nabakumar Bera、Debayan Sarkar

  DOI：10.1016/j.tet.2021.132367

  日期：2021.8

  A gold (III) catalyzed stereoselective cycloisomerization of 5-disubstituted-5-hydroxypent-2-yn alkanoate is described. The mild and efficient reaction condition delivers a series of di, tri-substituted dihydrofuran derivatives with high yield s along with an impressive diastereoselectivity. The reaction proceeds via a double [3,3] sigmatropic rearrangement with a concomitant 5-endo-dig cyclization

  描述了金 (III) 催化的 5-二取代-5-羟基戊-2-yn 链烷酸酯的立体选择性环异构化。温和高效的反应条件得到了一系列高收率的二、三取代二氢呋喃衍生物 秒以及令人印象深刻的非对映选择性。通过反应的进行双[3,3]σ重排与并用5-内切-挖环包围的丙二烯基中间体。
• Synthesis of dihydrofuran-3-one and 9,10-phenanthrenequinone hybrid molecules and biological evaluation against colon cancer cells as selective Akt kinase inhibitors
  作者：Jingjing Huang、Yufei Chen、Yinfeng Guo、Ming Bao、Kemiao Hong、Yuanqing Zhang、Wenhao Hu、Jinping Lei、Yongqiang Liu、Xinfang Xu

  DOI：10.1007/s11030-022-10458-w

  日期：——

  10-phenanthrenequinone hybrid compounds were synthetized through a one-pot gold-catalyzed oxidative cyclization and Aldol-type addition cascade reaction of homopropargylic alcohols with 9,10-phenanthrenequinone. The cytotoxicity of newly synthesized compounds was evaluated in CCK8 assay against different human cancer cells, showing significantly antiproliferative activity against tested tumor cell lines

  通过单锅金催化氧化环化和均炔醇与 9,10-菲醌的羟醛型加成级联反应，合成了一系列二氢呋喃-3-酮和 9,10-菲醌杂化化合物。在针对不同人类癌细胞的 CCK8 测定中评估了新合成化合物的细胞毒性，显示出针对测试肿瘤细胞系的显着抗增殖活性，其最低 IC 50值为 0.92 μM，高于 HCT-116。进一步研究表明，用有前途的化合物4c处理 HCT-116 细胞系作为选择性 Akt 抑制剂诱导细胞死亡。此外，对照实验和分子对接研究表明，显着的抗肿瘤活性可能归因于独特的杂化结构，这意味着这种双杂环杂化方法在发现具有结构多样性的新型生物活性分子方面具有广阔的潜力。 图形概要
• The Prevalence of Daytime Napping and Its Relationship to Nighttime Sleep
  作者：June J. Pilcher、Kristin R. Michalowski、Renee D. Carrigan

  DOI：10.1080/08964280109595773

  日期：2001.1

  Many healthy adults report daytime napping. Surprisingly few studies, however have examined spontaneous napping behavior especially very short naps, in healthy adults. The authors examined the prevalence of power naps (lasting less than 20 minutes) and longer naps (20 minutes or more) and their effects on nighttime sleep in a group of healthy young and middle-aged adults. The young and middle-aged adults reported very similar sleep and napping patterns, with approximately 74% of the participants in both groups reporting they had napped during a 7-day sleep-log period. Almost half of the participants reported that the average nap lasted less than 20 minutes. A multivariant analysis of variance (MANOVA) found no significant differences between the no-nap and the power-nap or long-nap groups in sleep quantity or quality for either age group. The current data suggested that power napping occurs frequently in healthy adults and that spontaneous napping does not negatively affect nighttime sleep.