(S)-3,4,4-trimethyl-1-pentyn-3-yl methanesulphonate | 107201-74-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: (S)-3,4,4-trimethyl-1-pentyn-3-yl methanesulphonate
• 英文别名: (R)-3,4,4-trimethyl-1-pentyn-3-ol methanesulfonate
• CAS: 107201-74-1
• 化学式: C₉H₁₆O₃S
• 分子量: 204.29
• InChiKey: VKRQDCRAGSHYDF-SECBINFHSA-N

物化性质

• 沸点：
  287.2±23.0 °C(Predicted)
• 密度：
  1.084±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13.0
• 可旋转键数：
  2.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (S)-3,4,4-trimethyl-1-pentyn-3-yl methanesulphonate 在 Li⁽¹⁺⁾*Br₃Cu₂H^(1-) 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 1-bromo-3,4,4-trimethylpenta-1,2-diene
  参考文献：
  名称：

  Stoichiometric cyclotrimerisation of chiral alkynes at a ruthenium centre: preparation of optically active (η6-arene)(η4-cycloocta-1,5-diene)ruthenium(0) complexes

  摘要：

  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.

  DOI：

  10.1016/s0022-328x(00)00881-0
• 作为产物：
  描述：

  (S)-3,4,4-trimethyl-1-pentyn-3-ol hydrogen phthalate 在 氢氧化钾 、 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 生成 (S)-3,4,4-trimethyl-1-pentyn-3-yl methanesulphonate
  参考文献：
  名称：

  Stoichiometric cyclotrimerisation of chiral alkynes at a ruthenium centre: preparation of optically active (η6-arene)(η4-cycloocta-1,5-diene)ruthenium(0) complexes

  摘要：

  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.

  DOI：

  10.1016/s0022-328x(00)00881-0

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。
• Caporusso, Anna Maria; Zoppi, Alessandra; Settimo, Federico Da, Gazzetta Chimica Italiana, 1985, vol. 115, # 5, p. 293 - 296
  作者：Caporusso, Anna Maria、Zoppi, Alessandra、Settimo, Federico Da、Lardicci, Luciano

  DOI：——

  日期：——