(R)-pentan-2-yl-4-methylbenzenesulfonate

• 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: (R)-pentan-2-yl-4-methylbenzenesulfonate
• 英文别名: (R)-2-tosyloxypentane；[(2R)-pentan-2-yl] 4-methylbenzenesulfonate
• 化学式: C₁₂H₁₈O₃S
• 分子量: 242.339
• InChiKey: HQSHAZLGVDYADJ-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  51.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-甲基-2-咪唑啉酮 、 (R)-pentan-2-yl-4-methylbenzenesulfonate 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以7%的产率得到(S)-1-methyl-3-(pentan-2-yl)imidazolidin-2-one
  参考文献：
  名称：

  Gold(I)-Catalyzed Amination of Allylic Alcohols with Cyclic Ureas and Related Nucleophiles

  摘要：

  A 1:1 mixture of [P(t-Bu)(2)-o-biphenyl]AuCl and AgSbF6 catalyzes the Intermolecular amination of allylic alcohols with 1-methylimidazolidin-2-one and related nucleophiles that, in the case of gamma-unsubstituted or gamma-methyl-substituted allylic alcohols, occurs with high gamma-regloselectivity and syn-stereoselectivity.

  DOI：

  10.1021/ol902923e
• 作为产物：
  描述：

  (R)-2-pentanol 、 对甲苯磺酰氯 在 吡啶 作用下， 反应 3.0h， 以84%的产率得到(R)-pentan-2-yl-4-methylbenzenesulfonate
  参考文献：
  名称：

  Gold(I)-Catalyzed Amination of Allylic Alcohols with Cyclic Ureas and Related Nucleophiles

  摘要：

  A 1:1 mixture of [P(t-Bu)(2)-o-biphenyl]AuCl and AgSbF6 catalyzes the Intermolecular amination of allylic alcohols with 1-methylimidazolidin-2-one and related nucleophiles that, in the case of gamma-unsubstituted or gamma-methyl-substituted allylic alcohols, occurs with high gamma-regloselectivity and syn-stereoselectivity.

  DOI：

  10.1021/ol902923e

文献信息

• Anti-selective alkylation of carboxylate enolates with 2-sulfonyloxyalkanes: A new route to optically active 2-arylalkanoic acids
  作者：Tetsuo Kusumoto、Satsuki Ichikawa、Kazunori Asaka、Ken-ichi Sato、Tamejiro Hiyama

  DOI：10.1016/0040-4039(94)02456-l

  日期：1995.2

  Reaction of arylacetic acid enolates with 2-tosyloxyalkanes gave with high anti-selectivity 2-aryl-3-methylalkanoic acids which were useful synthetic intermediates of ferroelectric liquid crystals.
• Gold(I)-Catalyzed Amination of Allylic Alcohols with Cyclic Ureas and Related Nucleophiles
  作者：Paramita Mukherjee、Ross A. Widenhoefer

  DOI：10.1021/ol902923e

  日期：2010.3.19

  A 1:1 mixture of [P(t-Bu)(2)-o-biphenyl]AuCl and AgSbF6 catalyzes the Intermolecular amination of allylic alcohols with 1-methylimidazolidin-2-one and related nucleophiles that, in the case of gamma-unsubstituted or gamma-methyl-substituted allylic alcohols, occurs with high gamma-regloselectivity and syn-stereoselectivity.