2-methyl-5-hexyn-3-ol | 54838-77-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-methyl-5-hexyn-3-ol
• 英文别名: (+/-)-2-methyl-5-hexyn-3-ol；2-methyl-hex-5-yn-3-ol；2-Methyl-hex-5-in-3-ol；2-Methylhex-5-yn-3-ol
• CAS: 54838-77-6
• 化学式: C₇H₁₂O
• mdl: MFCD16698299
• 分子量: 112.172
• InChiKey: UIOBNJCNIYKHRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.714
• 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：

  2-methyl-5-hexyn-3-ol 在 chromium(VI) oxide 、 硫酸 作用下， 以 丙酮 为溶剂， 生成 5,5-dimethyl-4-oxo-1,2-pentadiene
  参考文献：
  名称：

  Bertrand,M.; Le Gras,J., Bulletin de la Societe Chimique de France, 1962, p. 2136 - 2140

  摘要：

  DOI：
• 作为产物：
  描述：

  3-溴丙炔 在 四氢呋喃 、 aluminium amalgam 作用下， 生成 2-methyl-5-hexyn-3-ol
  参考文献：
  名称：

  The Prevalence of Daytime Napping and Its Relationship to Nighttime Sleep

  摘要：

  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.

  DOI：

  10.1080/08964280109595773

文献信息

• Substituierte Propargylcarbinole und ihre hypnotische Wirkung
  作者：H. Gutmann、O. Isler、G. Ryser、P. Zeller、B. Pellmont

  DOI：10.1002/hlca.19590420312

  日期：——

  Thirty tertiary propargylic carbinols have been prepared by condensing propargyl bromide with ketones. Some of them showed better hypnotic activity than 3-methylpentyn-3-01. The best compound of the series was 1-chloro-2-chloromethylpent-4-yn-2-01 which proved to be a very effective hypnotic with a favourable therapeutic index.

  通过使炔丙基溴与酮缩合制备了三十种叔炔丙基甲醇。其中一些表现出比3-甲基戊炔-3-01更好的催眠活性。该系列中最好的化合物是1-氯-2-氯甲基戊-4-yn-2-01，事实证明它是一种非常有效的催眠药，具有良好的治疗指数。
• Ni-Catalyzed regio- and stereoselective addition of arylboronic acids to terminal alkynes with a directing group tether
  作者：Madala Hari Babu、Gadi Ranjith Kumar、Ruchir Kant、Maddi Sridhar Reddy

  DOI：10.1039/c6cc10256e

  日期：——

  Addition of arylboronic acids to directing group tethered acetylenes in a regio and stereoselective manner using an inexpensive catalytic system is achieved for the first time to access highly sought after allyl/homoallyl alcohol/amine units.

  首次实现了使用廉价的催化体系以区域选择性和立体选择性的方式将芳基硼酸加成到系链的乙炔基上，从而获得了备受追捧的烯丙基/均烯丙基醇/胺单元。
• 1,2-Silyl-Migrative Cyclization of Vinylsilanes Bearing a Hydroxy Group:  Stereoselective Synthesis of Multisubstituted Tetrahydropyrans and Tetrahydrofurans¹
  作者：Katsukiyo Miura、Takeshi Hondo、Shigeo Okajima、Takahiro Nakagawa、Tatsuyuki Takahashi、Akira Hosomi

  DOI：10.1021/jo026006j

  日期：2002.8.1

  trans-2-alkyl-3-silyltetrahydropyrans 2 exclusively (trans/cis = >99/1 to 97/3). The cyclization efficiency and rate strongly depended on the geometry of the C-C double bond and the silyl group. The use of (E)-vinylsilanes resulted in lower yields with poor cis-selectivity. In the cyclization of (Z)-1 (R = Bu), the silyl group used, the reaction time, and the yield of 2 were as follows: SiMe(2)Ph, 9.5 h, 75%;

  已经研究了酸催化的羟基向α-烷基化的乙烯基硅烷的分子内加成。用5 mol％的TiCl（4）在CHCl（3）中处理（Z）-5-烷基-5-甲硅烷基-4-戊烯-1-醇1（R =烷基）得到反式-2-烷基-3-甲硅烷基四氢吡喃仅2个（trans / cis => 99/1至97/3）。环化效率和速率很大程度上取决于CC双键和甲硅烷基的几何形状。（E）-乙烯基硅烷的使用导致较低的收率和较差的顺式选择性。在（Z）-1（R ＝ Bu）的环化中，所用的甲硅烷基基团，反应时间和2的产率如下：SiMe（2）Ph，9.5h，75％； m / z。SiMe（3），7.5小时，66％；SiMePh（2），24小时，58％；SiMe（2）-t-Bu，0.75小时，85％; SiMe（2）Bn，1.5 h，78％。该1，2-甲硅烷基迁移环化可用于三取代四氢吡喃的立体选择性合成。1-，2-或3-取代的（Z）-5-甲硅烷基-
• Photocatalytic Sulfonylcarbocyclization of Alkynes Using SEt as a Traceless Directing Group: Access to Cyclopentenes and Indenes
  作者：Yulu Zhou、Yizhou Qin、Qinggui Wang、Zuxiao Zhang、Gangguo Zhu

  DOI：10.1002/anie.202110864

  日期：2022.1.3

  A photocatalytic sulfonylcarbocyclization of terminal alkynes using SEt as a traceless directing group is developed, providing a facile access to highly substituted cyclopentenes and indenes from readily available starting materials. It represents a new advance on anti-Baldwin 5-endo-trig radical cyclization of all-carbon systems, which may be valuable for the fast construction of five-membered carbocycles

  开发了使用 SEt 作为无痕导向基团的末端炔烃的光催化磺酰基碳环化，提供了从容易获得的起始材料中轻松获得高度取代的环戊烯和茚的方法。它代表了全碳系统的反鲍德温 5-endo-trig 自由基环化的新进展，这可能对快速构建五元碳环很有价值。
• Hydroalkylation of Alkynyl Ethers via a Gold(I)-Catalyzed 1,5-Hydride Shift/Cyclization Sequence
  作者：Igor Dias Jurberg、Yann Odabachian、Fabien Gagosz

  DOI：10.1021/ja9100134

  日期：2010.3.17

  A series of alkynyl ethers react with an electrophilic gold(I) catalyst to produce a range of structurally complex spiro or fused dihydrofurans and dihydropyrans via a 1,5-hydride shift/cyclization sequence. This hydroalkylation process, which is performed under practical experimental conditions, can be applied to terminal as well as ester-substituted alkynes. It allows the efficient conversion of

  一系列炔基醚与亲电子金 (I) 催化剂反应，通过 1,5-氢化物转移/环化序列产生一系列结构复杂的螺或稠合二氢呋喃和二氢吡喃。这种在实际实验条件下进行的加氢烷基化过程可应用于末端和酯取代的炔烃。它允许通过将乙烯基金物质亲核加成到氧鎓中间体上，将二级或三级 sp(3) CH 键有效转化为新的 CC 键。形成新的五元或六元环的环异构化过程的立体选择性似乎取决于空间因素和炔烃取代模式。