methyl (R)-2-(4-bromophenyl)-1-phenylethanesulfonate

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: methyl (R)-2-(4-bromophenyl)-1-phenylethanesulfonate
• 英文别名: methyl (1R)-2-(4-bromophenyl)-1-phenylethanesulfonate
• 化学式: C₁₅H₁₅BrO₃S
• 分子量: 355.252
• InChiKey: WVSPTFFLDQXJGW-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.71
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  苄磺酰氯 在 palladium diacetate 正丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 121.0h， 生成 methyl (R)-2-(4-bromophenyl)-1-phenylethanesulfonate
  参考文献：
  名称：

  Efficient asymmetric synthesis of α-alkylated benzylic methyl sulfonates

  摘要：

  The first highly efficient auxiliary-controlled synthesis of various alpha-substituted sulfortic acid derivatives is described. Alkyl or aryl halides were reacted with lithiated benzylic sulfortic esters bearing 1,2:5,6-di-O-isopropylidene-alpha-D-allofuranose as a removable enantiopure alcohol auxiliary to give the alkylated products in excellent diastereomeric excesses. The racemization-free cleavage conditions provided highly enantioenriched sulfonic acid derivatives (ee >= 98%). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.046

文献信息

• Efficient asymmetric synthesis of α-alkylated benzylic methyl sulfonates
  作者：Dieter Enders、Nicola Vignola、Otto M. Berner、Wacharee Harnying

  DOI：10.1016/j.tet.2005.01.046

  日期：2005.3

  The first highly efficient auxiliary-controlled synthesis of various alpha-substituted sulfortic acid derivatives is described. Alkyl or aryl halides were reacted with lithiated benzylic sulfortic esters bearing 1,2:5,6-di-O-isopropylidene-alpha-D-allofuranose as a removable enantiopure alcohol auxiliary to give the alkylated products in excellent diastereomeric excesses. The racemization-free cleavage conditions provided highly enantioenriched sulfonic acid derivatives (ee >= 98%). (c) 2005 Elsevier Ltd. All rights reserved.