2-methyl-5-phenyl-hex-3-yne-2,5-diol | 23695-53-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-methyl-5-phenyl-hex-3-yne-2,5-diol
• 英文别名: 2-Methyl-5-phenyl-hex-3-in-2,5-diol；(+/-)-2.5-Dihydroxy-2-methyl-5-phenyl-hexin-(3)；2-Methyl-5-phenyl-hexin-(3)-diol-(2,5)；5-Methyl-2-phenyl-hexin-(3)-diol-(2,5)；2-Methyl-5-phenylhex-3-yne-2,5-diol
• CAS: 23695-53-6
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: WEAHJVGMHZDNNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methyl-5-phenyl-hex-3-yne-2,5-diol 在 钯 、 乙酸乙酯 作用下， 19.0 ℃ 、99.06 kPa 条件下， 生成 2-methyl-5-phenyl-hex-3-ene-2,5-diol
  参考文献：
  名称：

  Salkind; Iwanow, Zhurnal Obshchei Khimii, 1941, vol. 11, p. 803,810, 815

  摘要：

  DOI：
• 作为产物：
  描述：

  乙基溴化镁 、 2-甲基-3-丁炔-2-醇 在 乙醚 作用下， 生成 2-methyl-5-phenyl-hex-3-yne-2,5-diol
  参考文献：
  名称：

  Salkind; Iwanow, Zhurnal Obshchei Khimii, 1941, vol. 11, p. 803,810, 815

  摘要：

  DOI：

文献信息

• Gold-Catalyzed Stereocontrolled Synthesis of 2,3-Bis(acetoxy)-1,3-dienes
  作者：Xiaogen Huang、Teresa de Haro、Cristina Nevado

  DOI：10.1002/chem.200900391

  日期：2009.6.8

  the stereochemistry: 2,3‐Bis(acetoxy)‐1,3‐dienes are obtained in a stereocontrolled manner by a novel tandem 1,2‐/1,2‐bis(acetoxy) rearrangement (see scheme, R1 and R2 are δ+ stabilizing). Upon stabilization of the reaction intermediates, the ligand attached to gold controls the stereochemistry of the alkene in the second acetate migration, that is, N‐heterocyclic carbenes (NHC) favor cis alkenes, whereas

  改变配体，改变立体化学：通过新的串联1,2- / 1,2-双（乙酰氧基）重排以立体控制方式获得2,3-双（乙酰氧基）-1,3-二烯（参见方案， R 1和R 2为δ +稳定化。反应中间体稳定后，与金连接的配体控制了第二次乙酸盐迁移过程中烯烃的立体化学，即N-杂环卡宾（NHC）有利于顺式烯烃，而膦配体则选择性地提供了反式烯烃。
• One-step Synthesis of Fulgides by Palladium-catalyzed Carbonylation of Substituted 2-Butyne-1,4-diols
  作者：Jitsuo Kiji、Hisatoshi Konishi、Tamon Okano、Shinji Kometani、Akio Iwasa

  DOI：10.1246/cl.1987.313

  日期：1987.2.5

  The reaction of carbon monoxide with substituted 2-butyne-1,4-diols by pd(OAc)2/I2 catalyst gives derivatives of dimethylenesuccinic anhydride, “fulgides”, in high yields.

  在 pd(OAc)2/I2 催化剂的作用下，一氧化碳与取代的 2-丁炔-1,4-二醇发生反应，产生了高产率的二亚甲基丁二酸酐衍生物 "富尔酸盐"。
• Korobizyna et al., Zhurnal Obshchei Khimii, 1959, vol. 29, p. 3880,3882; engl. Ausg. S. 3839, 3841
  作者：Korobizyna et al.

  DOI：——

  日期：——
• Babajan, Zhurnal Obshchei Khimii, 1940, vol. 10, p. 1177,1181
  作者：Babajan

  DOI：——

  日期：——
• Iron-Catalyzed Cyclization of Alkynols with Diorganyl Diselenides: Synthesis of 2,5-Dihydrofuran, 3,6-Dihydro-2<i>H</i>-pyran, and 2,5-Dihydro-1<i>H</i>-pyrrole Organoselanyl Derivatives
  作者：Kamila K. Casola、Davi F. Back、Gilson Zeni

  DOI：10.1021/acs.joc.5b01448

  日期：2015.8.7

  An iron-catalyzed system, using diorganyl diselenides as an organoselenium source, was used for the cyclization of 1,4-butyne-diols in the preparation of 3,4-bis(organoselany1)-2,5-dihydrofurans. The optimized reaction conditions are compatible with many functional groups in 1,4-butyne-diols and diorganyl diselenides. In addition, this catalyst system was also efficient with diorganyl disulfides, but it did not work for diorganyl ditellurides. The same reaction conditions were also extended to pentyne-1,5diol for the preparation of 4,5-bis(organoselany1)-3,6-dihydro-2H-pyrans and to 4-amino-butynol for the preparation of 2,5-dihydro1H-pyrrole derivatives. The synthetic utility of these heterocycles was studied using 5-bis(organoselany1)-3,6-dihydro-2H-pyrans as substrate in a Kumada-type cross-coupling reaction.