(R)-3,4,4-trimethyl-1-pentyn-3-ol | 38484-41-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-3,4,4-trimethyl-1-pentyn-3-ol
• 英文别名: (S)-3,4,4-trimethyl-1-pentyn-3-ol；(S)-3,4,4-trimethyl-pent-1-yn-3-ol；(S)-3,4,4-Trimethyl-pent-1-in-3-ol；(R)(-)-3,4,4-Trimethyl-pent-1-in-3-ol；(-)-3,4,4-Trimethyl-pent-1-in-3-ol；(-)-3,4,4-Trimethylpent-1-in-3-ol；1-Pentyn-3-ol, 3,4,4-trimethyl-, (S)-；(3S)-3,4,4-trimethylpent-1-yn-3-ol
• CAS: 38484-41-2
• 化学式: C₈H₁₄O
• 分子量: 126.199
• InChiKey: XXWIEGOAVMLISY-MRVPVSSYSA-N

物化性质

• 沸点：
  45-47 °C(Press: 15 Torr)
• 密度：
  0.889±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  9
• 可旋转键数：
  2
• 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：

  (R)-3,4,4-trimethyl-1-pentyn-3-ol 在 氢溴酸 、 铜 、 溴化铵 、 copper(I) bromide 作用下， 以 二乙二醇二甲醚 为溶剂， 生成 1-bromo-3,4,4-trimethyl-penta-1,2-diene
  参考文献：
  名称：

  Landor,S.R. et al., Journal of the Chemical Society. Perkin transactions II, 1972, p. 1995 - 1998

  摘要：

  DOI：
• 作为产物：
  描述：

  频哪酮 在 sodium 、 ferric nitrate 作用下， 以 氨 为溶剂， 生成 (R)-3,4,4-trimethyl-1-pentyn-3-ol
  参考文献：
  名称：

  283.艾伦。第四部分。光学活性的烯丙基氯的合成

  摘要：

  DOI：

  10.1039/jr9630001506

文献信息

• Reaction of 1-bromo-1,2-dienes with alkylcuprates as a regio- and stereo-selective route to acetylenic or allenic compounds
  作者：Carmela Polizzi、Carla Consoloni、Luciano Lardicci、Anna Maria Caporusso

  DOI：10.1016/0022-328x(91)80179-n

  日期：1991.10

  Alkylcuprates react with 1-bromo-1,2-dienes to give allenic and/or acetylenic products. The selectivity of the crosscoupling is markedly dependent on the nature of the copper reagent, which plays a prominent role in determining both the regio- and the stereo-chemistry. The preparative aspects of these copper-induced reactions are discussed and their possible mechanism discussed.

  烷基杯酸酯与1-溴-1,2-二烯反应生成烯丙基和/或炔属产物。交叉偶联的选择性显着取决于铜试剂的性质，铜试剂在决定区域化学和立体化学方面都起着重要的作用。讨论了这些铜诱导的反应的制备方面，并讨论了其可能的机理。
• Permethylated .beta.-Cyclodextrin as Chiral Solvating Agent for the NMR Assignment of the Absolute Configuration of Chiral Trisubstituted Allenes
  作者：Gloria Uccello-Barretta、Federica Balzano、Anna Maria Caporusso、Antonietta Iodice、Piero Salvadori

  DOI：10.1021/jo00112a050

  日期：1995.4

  Permethylated beta-cyclodextrin is a convenient chiral solvating agent (CSA) for the determination by NMR of the enantiomeric purities of chiral trisubstituted allenes and of their absolute configuration. Al the allene proton resonances are deshielded, and this effect is stronger for the (S)-enantiomer of the allene than for the (R)-enantiomer.
• 464. Allenes. Part VI. The absolute configuration of 3,4,4-trimethylpent-1-yn-3-ol and 1-chloro-3,4,4-trimethylpenta-1,2-diene
  作者：R. J. D. Evans、S. R. Landor

  DOI：10.1039/jr9650002553

  日期：——
• Stoichiometric cyclotrimerisation of chiral alkynes at a ruthenium centre: preparation of optically active (η6-arene)(η4-cycloocta-1,5-diene)ruthenium(0) complexes
  作者：Paolo Pertici、Alessandra Verrazzani、Emanuela Pitzalis、Anna Maria Caporusso、Giovanni Vitulli

  DOI：10.1016/s0022-328x(00)00881-0

  日期：2001.3

  The chiral alkynes (S)-MeCH(R)-C drop CH. 2 (R = Et, 3-methyl-1-pentyne, a; 'Pr, 3,4-dimethyl-1-pentyne, b;'Bu, 3,4,4-trimethyl-1-pentyne, c), containing a stereogenic centre in alpha position to the triple bond, react at room temperature with the complex Ru(eta (6)-naphthalene)(eta (4)-COD). 1. to give the corresponding optically active complexes Ru (eta (6)-(S)-1, 3, 5-C6H3[CH(Me)R](3)} (eta (4)-COD), 6, and Ru(eta (6)-(S)-1,2,4-C6H3[CH(Me)R](3)}(eta (4)-COD), 7. the eta (6)-1.3.5-arene regioisomer being the prevalent product. With (S)-2a, a mixture of 6a and 7a (6a/7a = 90:10) is obtained and, with the more sterically demanding alkynes (S)-2b and (S)-2c, the regioselectivity to the corresponding complexes 6b and 6c is almost complete. This synthetic procedure does not involve the stereogenic centres on the alkynes and it proceeds with complete stereoselectivity. (C) 2001 Elsevier Science B.V. All rights reserved.
• Landor; Taylor-Smith, Proceedings of the Chemical Society, London, 1959, p. 154
  作者：Landor、Taylor-Smith

  DOI：——

  日期：——