p-Bromphenylglyoxal-methylhemimercaptal | 13603-52-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-Bromphenylglyoxal-methylhemimercaptal
• 英文别名: 1-(4-bromophenyl)-2-hydroxy-2-(methylthio)ethan-1-one
• CAS: 13603-52-6
• 化学式: C₉H₉BrO₂S
• 分子量: 261.139
• InChiKey: CXHIRTNBFRBWMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.31
• 重原子数：
  13.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  p-Bromphenylglyoxal-methylhemimercaptal 在 sodium tetrahydroborate 、 copper(II) sulfate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 28.0h， 生成 (S_S)-2-amino-1-(4-bromophenyl)-N-(tert-butanesulfinyl)ethan-1-ol 、 (S_S)-2-amino-1-(4-bromophenyl)-N-(tert-butanesulfinyl)ethan-1-ol
  参考文献：
  名称：

  Stereoselective allylation and reduction of N - tert -butanesulfinyl-α-keto aldimines

  摘要：

  A simple methodology for the synthesis of N-tert-butanesulfinyl-alpha-keto aldimines from both alpha-keto aldehydes and carboxylic esters has been developed. The addition of an in situ formed allyl indium reagent to these chiral imines was also studied. The addition took place in a sequential manner, first to the imine group with excellent diastereoselectivity and then to the carbonyl group with lower diastereoselectivity. Ruthenium-catalyzed ring closing metathesis of the resulting 5-aminoocta-1,7-dien-4-ol derivatives provided access to 6-aminocyclohex-3-enols. Reduction of the alpha-keto aldimines led to N-tert-butanesulfinyl-1,2-aminoalcohols as a 1:1 diastereomeric mixture. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2017.08.010
• 作为产物：
  描述：

  CH3CSCH2COC6H4Br-p 在 盐酸 、 水 、 二甲基亚砜 作用下， 反应 24.0h， 以1.754 g的产率得到p-Bromphenylglyoxal-methylhemimercaptal
  参考文献：
  名称：

  Stereoselective allylation and reduction of N - tert -butanesulfinyl-α-keto aldimines

  摘要：

  A simple methodology for the synthesis of N-tert-butanesulfinyl-alpha-keto aldimines from both alpha-keto aldehydes and carboxylic esters has been developed. The addition of an in situ formed allyl indium reagent to these chiral imines was also studied. The addition took place in a sequential manner, first to the imine group with excellent diastereoselectivity and then to the carbonyl group with lower diastereoselectivity. Ruthenium-catalyzed ring closing metathesis of the resulting 5-aminoocta-1,7-dien-4-ol derivatives provided access to 6-aminocyclohex-3-enols. Reduction of the alpha-keto aldimines led to N-tert-butanesulfinyl-1,2-aminoalcohols as a 1:1 diastereomeric mixture. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2017.08.010