(RS,SR)-N-(2,3-dihydroxy-1-phenylpropyl)-4-toluenesulfonamide

• 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: (RS,SR)-N-(2,3-dihydroxy-1-phenylpropyl)-4-toluenesulfonamide
• 英文别名: N-[(1S,2R)-2,3-dihydroxy-1-phenylpropyl]-4-methylbenzenesulfonamide
• 化学式: C₁₆H₁₉NO₄S
• 分子量: 321.397
• InChiKey: FDTSHBAKZPTUHQ-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  95
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (RS,SR)-N-(2,3-dihydroxy-1-phenylpropyl)-4-toluenesulfonamide 在 咪唑 、 碘 、 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以94%的产率得到4-methyl-N-(1-phenylallyl)benzenesulfonamide
  参考文献：
  名称：

  Introduction of Functionalized C1, C2, and C3 Units to Imines through the Dimethylzinc−Air-Initiated Radical Addition

  摘要：

  Introduction of functionalized C1, C2, and C3 units to imines was achieved by using the dimethylzinc-air-initiated alpha-alkoxyalkyl radical addition as a key reaction. The addition to a C= N double bond chemoselectively occurred in the presence of a C=O double bond, which is one of the advantages of this radical addition reaction over ionic addition reactions.

  DOI：

  10.1021/jo035496s
• 作为产物：
  描述：

  N-[α-(2,2-dimethyl-1,3-dioxolan-4-yl)benzyl]-4-toluenesulfonamide 在 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.0h， 生成 (RS,SR)-N-(2,3-dihydroxy-1-phenylpropyl)-4-toluenesulfonamide 、 (RS,RS)-N-(2,3-dihydroxy-1-phenylpropyl)-4-toluenesulfonamide
  参考文献：
  名称：

  Introduction of Functionalized C1, C2, and C3 Units to Imines through the Dimethylzinc−Air-Initiated Radical Addition

  摘要：

  Introduction of functionalized C1, C2, and C3 units to imines was achieved by using the dimethylzinc-air-initiated alpha-alkoxyalkyl radical addition as a key reaction. The addition to a C= N double bond chemoselectively occurred in the presence of a C=O double bond, which is one of the advantages of this radical addition reaction over ionic addition reactions.

  DOI：

  10.1021/jo035496s

文献信息

• Asymmetric Radical Addition of Ethers to Enantiopure <i>N</i>-<i>p</i>-Toluenesulfinyl Aldimines, Mediated by Dimethylzinc−Air
  作者：Tito Akindele、Yasutomo Yamamoto、Masaru Maekawa、Hiroyuki Umeki、Ken-ichi Yamada、Kiyoshi Tomioka

  DOI：10.1021/ol0621093

  日期：2006.12.1

  Asymmetric radical addition of ethers to enantiopure aromatic N-p-toluenesulfinyl aldimines has been achieved. The requisite radicals were generated by dimethylzinc-air. Lewis acid activation of the N-p-toluenesulfinyl aldimines followed by radical addition gives a mixture of sulfinamide and sulfonamide products. Subsequent treatment of the mixture with dry m-CPBA affords the sulfonamide product in

  已经实现了醚向不纯的芳族Np-甲苯亚磺酰基醛亚胺的不对称自由基加成。必需的自由基是由二甲基锌-空气生成的。N-甲苯亚磺酰基醛亚胺的路易斯酸活化，然后自由基加成，得到亚磺酰胺和磺酰胺产物的混合物。随后用干燥的m-CPBA处理混合物，得到对映体富集形式的磺酰胺产物。[反应：看文字]
• Osmium-catalyzed vicinal oxyamination of olefins by Chloramine-T
  作者：K. B. Sharpless、A. O. Chong、Koichiro Oshima

  DOI：10.1021/jo00863a052

  日期：1976.1
• Introduction of Functionalized C1, C2, and C3 Units to Imines through the Dimethylzinc−Air-Initiated Radical Addition
  作者：Ken-ichi Yamada、Yasutomo Yamamoto、Masaru Maekawa、Kiyoshi Tomioka

  DOI：10.1021/jo035496s

  日期：2004.3.1

  Introduction of functionalized C1, C2, and C3 units to imines was achieved by using the dimethylzinc-air-initiated alpha-alkoxyalkyl radical addition as a key reaction. The addition to a C= N double bond chemoselectively occurred in the presence of a C=O double bond, which is one of the advantages of this radical addition reaction over ionic addition reactions.