N-tosyl-5-bromo-2-thiophenecarboxaldehyde imine

• 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: N-tosyl-5-bromo-2-thiophenecarboxaldehyde imine
• 英文别名: N-[(5-bromothiophen-2-yl)methylidene]-4-methylbenzenesulfonamide
• 化学式: C₁₂H₁₀BrNO₂S₂
• 分子量: 344.253
• InChiKey: XNYKKSNNJDQZAG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  83.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  重氮乙酸甲酯 、 N-tosyl-5-bromo-2-thiophenecarboxaldehyde imine 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以82%的产率得到methyl 2-diazo-3-[2-(5-bromo)thienyl]-3-[(N-tosyl)amino]propanoate
  参考文献：
  名称：

  Concise and diastereoselective approach to syn- and anti-N-tosyl-α-hydroxy β-amino acid derivatives

  摘要：

  The methyl diazoacetate and aryl (N-tosyl)imines can be transformed into syn or anti a-hydroxy P-amino esters with high diastereoselectivities in three steps: the base promoted nucleophilic condensation of the methyl diazoacetate and aryl (N-tosyl)imines to give beta-(N-tosyl)amino alpha-diazoesters, followed by oxidation with Oxoneo to generate alpha-oxo esters, which were reduced with NaBH4 to yield the anti-N-losyl-alpha-hydroxy beta-amino ester, or hydrogenated with Pd/C (10%) as the catalyst to yield corresponding syn isomer, both in high diastereoselectivity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.04.054

文献信息

• Stereoselective nucleophilic addition of chiral lithium enolates to (N-tosyl)imines: enantioselective synthesis of β-aryl-β-amino acid derivatives
  作者：Zhihua Ma、Yonghua Zhao、Nan Jiang、Xianglin Jin、Jianbo Wang

  DOI：10.1016/s0040-4039(02)00498-7

  日期：2002.4

  Nucleophilic addition of the chiral lithium enolates of (S)-(−)-4-benzyl-2-oxazolidinone acetamide with N-tosyl arylaldehyde imines gives β-aryl-β-amino acid derivatives in good yields and excellent diastereoselectivity.

  （S）-（-）-4-苄基-2-恶唑烷酮乙酰胺的手性烯醇锂与N-甲苯磺酰基芳醛亚胺的亲核加成得到β-芳基-β-氨基酸衍生物，产率高，非对映选择性高。
• A Highly Stereoselective Addition of the Anion Derived from ?-Diazoacetamide to AromaticN-Tosylimines
  作者：Yonghua Zhao、Zhihua Ma、Xiaomei Zhang、Yaping Zou、Xianglin Jin、Jianbo Wang

  DOI：10.1002/anie.200460730

  日期：2004.11.12
• Concise and diastereoselective approach to syn- and anti-N-tosyl-α-hydroxy β-amino acid derivatives
  作者：Yonghua Zhao、Nan Jiang、Shufeng Chen、Cheng Peng、Xiaomei Zhang、Yaping Zou、Shiwei Zhang、Jianbo Wang

  DOI：10.1016/j.tet.2005.04.054

  日期：2005.7

  The methyl diazoacetate and aryl (N-tosyl)imines can be transformed into syn or anti a-hydroxy P-amino esters with high diastereoselectivities in three steps: the base promoted nucleophilic condensation of the methyl diazoacetate and aryl (N-tosyl)imines to give beta-(N-tosyl)amino alpha-diazoesters, followed by oxidation with Oxoneo to generate alpha-oxo esters, which were reduced with NaBH4 to yield the anti-N-losyl-alpha-hydroxy beta-amino ester, or hydrogenated with Pd/C (10%) as the catalyst to yield corresponding syn isomer, both in high diastereoselectivity. (c) 2005 Elsevier Ltd. All rights reserved.