2-methyl-4-pentyn-1-ol | 58113-69-2

• 分子结构分类: 有机化合物 - 乙炔化物
• 英文名称: 2-methyl-4-pentyn-1-ol
• 英文别名: methyl-2 pentyn-4 ol-1；2-methyl-pent-4-yn-1-ol；2-Methyl-pent-4-in-1-ol；4-Methyl-5-hydroxy-pent-1-in；2-Methylpent-4-yn-1-ol
• CAS: 58113-69-2
• 化学式: C₆H₁₀O
• 分子量: 98.1448
• InChiKey: CUJNHYUUEHYUIY-UHFFFAOYSA-N

物化性质

• 沸点：
  159 °C
• 密度：
  0.899 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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-4-pentyn-1-ol 在 sodium amide 、 碘甲烷 作用下， 以 苯 为溶剂， 反应 138.0h， 生成 (+/-)-xyloketal D
  参考文献：
  名称：

  Total Synthesis of (±)-Xyloketal D and Model Studies towards the Total Synthesis of (-)-Xyloketal A

  摘要：

  DOI：

  10.3987/com-03-s(p)37
• 作为产物：
  描述：

  2-甲基戊-4-炔酸 在 lithium aluminium tetrahydride 、 乙醚 作用下， 生成 2-methyl-4-pentyn-1-ol
  参考文献：
  名称：

  Buchta; Schlesinger, Justus Liebigs Annalen der Chemie, 1955, vol. 598, p. 1,22

  摘要：

  DOI：

文献信息

• 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-
• (+)-Isocryptotanshinone derivatives and its simplified analogs as STAT3 signaling pathway inhibitors
  作者：Xiang Shi、Ting ting Du、Zhihui Zhang、Xiaoyu Liu、Ying Yang、Nina Xue、Xiaozhen Jiao、Xiaoguang Chen、Ping Xie

  DOI：10.1016/j.bioorg.2022.106015

  日期：2022.10

  transducer and activator of transcription-3 (STAT3) signaling pathway inhibitory activity, shows significant inhibitory activity against several tumors. In this study, a series of ICTS derivatives and simplified analogs containing a 1, 4-naphthoquinone core was designed, synthesized, and evaluated. The results demonstrated that most target compounds were potent STAT3 signaling pathway inhibitors based

  异隐丹参酮 (ICTS) 是一种天然产物，具有潜在的信号转导和转录激活剂 3 (STAT3) 信号通路抑制活性，对多种肿瘤具有显着的抑制活性。在这项研究中，设计、合成和评估了一系列含有 1, 4-萘醌核心的 ICTS 衍生物和简化的类似物。结果表明，大多数目标化合物是有效的 STAT3 信号通路抑制剂，基于其抑制 STAT3 磷酸化的机制。此外，基于获得的数据，结构 - 活性关系（SAR）被合理推导。同时，化合物16r的分子对接建议其与 STAT3 的可能交互模式。为了进一步验证抗癌活性，使用 HCT116、HepG 2、MCF-7、A549 和 U251 细胞系测试了所有目标化合物。有趣的是，与不同的肿瘤细胞系相比，HCT-116 细胞系被确定为最敏感。此外，化合物21e、16r、28a和16e显示出对 HCT116 细胞生长的剂量依赖性抑制。因此，确定了 ICTS 衍生物及其简化类似物的
• Relative Asymmetric Induction in the Intramolecular Reaction between Alkynes and Cyclopropylcarbene−Chromium Complexes:  Stereocontrolled Synthesis of Five-Membered Rings Fused to Oxygen Heterocycles
  作者：Jingbo Yan、Jin Zhu、Julius J. Matasi、James W. Herndon

  DOI：10.1021/jo982144q

  日期：1999.2.1

  Synthesis of cyclopentenone derivatives fused to oxygen heterocycles by means of the intramolecular coupling of alkynes and cyclopropylcarbene-chromium complexes has been examined for a variety of cases in which the tethering chain features a stereogenic center. In some cases, this process proceeds with a very high degree of stereoselectivity; however, the extent and direction of relative asymmetric induction is very dependent upon the position of the chiral atom within the tethering chain and the length of the tethering chain. In the best case, featuring a two-carbon tether and a stereogenic center at the homopropargylic position (complex 1N), the heterocyclic ring was produced with 97:3 selectivity for the cis heterocycle (3N). In the worst case, featuring a three-carbon tether and a stereogenic center at the homopropargylic position (complexes 1F and ii), no stereoselectivity was observed. Improvement in stereoselectivity was noticed when terminal alkynes were replaced by silylated alkynes and when proton sources were eliminated from the reaction.
• Discovery of a Photoinduced Dark Catalytic Cycle Using <i>in Situ</i> LED-NMR Spectroscopy
  作者：Dan Lehnherr、Yining Ji、Andrew J. Neel、Ryan D. Cohen、Andrew P. J. Brunskill、Junyu Yang、Mikhail Reibarkh

  DOI：10.1021/jacs.8b08596

  日期：2018.10.24

  We report the use of LED-NMR spectroscopy to study the reaction mechanism of a newly discovered photoinduced iron-catalyzed cycloisomerization of alkynols to cyclic enol ethers. By understanding on/off ligand binding to the catalyst, we were able to appropriately design reaction conditions to balance catalyst activity and stability. LED-NMR was demonstrated to be a powerful tool in elucidating reaction mechanisms of photochemical reactions. Temporal NMR spectroscopic data under visible light illumination (1) revealed the pre-catalyst activation mechanism, (2) proved that photon flux provides a unique external control of the equilibrium distribution between the pre-catalyst and active catalyst, and ultimately the rate of reaction, (3) provided information about the reaction driving forces and the turnover-limiting step, and (4) enabled both real-time structural and kinetic insights into elusive species (e.g., dissolved gases).
• Colonge,J. et al., Bulletin de la Societe Chimique de France, 1966, p. 2005 - 2011
  作者：Colonge,J. et al.

  DOI：——

  日期：——