(R)-1-叠氮基-4-(甲基亚磺酰)-丁烷 | 155185-01-6

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 中文名称: (R)-1-叠氮基-4-(甲基亚磺酰)-丁烷
• 中文别名: (R)-1-叠氮基-4-(甲基亚磺酰基)-丁烷
• 英文名称: (R)-(-)-1-azido-4-(methylsulfinyl)butane
• 英文别名: (R)-4-Azidobutyl methyl sulfoxide；(R)-1-Azido-4-(methylsulfinyl)-butane；1-azido-4-[(R)-methylsulfinyl]butane
• CAS: 155185-01-6
• 化学式: C₅H₁₁N₃OS
• 分子量: 161.228
• InChiKey: SCBWZMZIFFMINE-SNVBAGLBSA-N

物化性质

• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  二硫化碳 、 (R)-1-叠氮基-4-(甲基亚磺酰)-丁烷 在 三苯基膦 作用下， 生成 (S)-Sulforaphane
  参考文献：
  名称：

  Asymmetric Synthesis of Chiral Sulfinate Esters and Sulfoxides. Synthesis of Sulforaphane

  摘要：

  Reaction of the chiral auxiliary trans-2-phenylcyclohexanol (1) with thionyl chloride afforded a nearly equal mixture of two diastereomeric chlorosulfite esters (6); Treatment of this mixture with an equivalent amount of a dialkylzinc reagent (Me, et, i-Pr) afforded high levels of conversion of both chlorosulfite esters to (mainly) a single diastereomer of the sulfinate ester (7). Levels of absolute stereochemical induction ranged from 10:1 to 96:4 under conditions affording high chemical yields. The method was employed for the separate synthesis of both enantiomers of sulforaphane (13).

  DOI：

  10.1021/jo00082a016
• 作为产物：
  描述：

  (R)-4-(tert-Butyldimethylsiloxy)butyl methyl sulfoxide 在 sodium azide 、 氢氟酸 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 14.5h， 生成 (R)-1-叠氮基-4-(甲基亚磺酰)-丁烷
  参考文献：
  名称：

  Asymmetric Synthesis of Chiral Sulfinate Esters and Sulfoxides. Synthesis of Sulforaphane

  摘要：

  Reaction of the chiral auxiliary trans-2-phenylcyclohexanol (1) with thionyl chloride afforded a nearly equal mixture of two diastereomeric chlorosulfite esters (6); Treatment of this mixture with an equivalent amount of a dialkylzinc reagent (Me, et, i-Pr) afforded high levels of conversion of both chlorosulfite esters to (mainly) a single diastereomer of the sulfinate ester (7). Levels of absolute stereochemical induction ranged from 10:1 to 96:4 under conditions affording high chemical yields. The method was employed for the separate synthesis of both enantiomers of sulforaphane (13).

  DOI：

  10.1021/jo00082a016

文献信息

• Enantiopure Sulforaphane Analogues with Various Substituents at the Sulfinyl Sulfur: Asymmetric Synthesis and Biological Activities
  作者：Noureddine Khiar、Sabine Werner、Siham Mallouk、Franziska Lieder、Ana Alcudia、Inmaculada Fernández

  DOI：10.1021/jo9007749

  日期：2009.8.21

  A convergent and high-yielding approach for the asymmetric synthesis of sulforaphane 2 and four analogues differently substituted at the sulfinyl sulfur has been developed. The key step of the synthesis is the diastereoselective synthesis of sulfinate ester 23-SS, using the DAG (diacetone-d-glucofuranose)-methodology. The biological activity of these compounds as inductors of phase II detoxifying enzyme

  已开发出一种收敛性和高产率的方法，用于不对称合成萝卜硫烷2和在亚磺酰基硫上被不同取代的四个类似物。合成的关键步骤是亚磺酸酯的非对映合成23 -小号小号，使用DAG（diacetone- d -glucofuranose）-methodology。通过确定它们激活细胞保护性转录因子Nrf2的能力，研究了这些化合物作为II期解毒酶诱导剂的生物活性。
• Asymmetric Synthesis of Chiral Sulfinate Esters and Sulfoxides. Synthesis of Sulforaphane
  作者：James K. Whitesell、Man-Shing Wong

  DOI：10.1021/jo00082a016

  日期：1994.2

  Reaction of the chiral auxiliary trans-2-phenylcyclohexanol (1) with thionyl chloride afforded a nearly equal mixture of two diastereomeric chlorosulfite esters (6); Treatment of this mixture with an equivalent amount of a dialkylzinc reagent (Me, et, i-Pr) afforded high levels of conversion of both chlorosulfite esters to (mainly) a single diastereomer of the sulfinate ester (7). Levels of absolute stereochemical induction ranged from 10:1 to 96:4 under conditions affording high chemical yields. The method was employed for the separate synthesis of both enantiomers of sulforaphane (13).