3-Hydroxy-2-(naphthalene-1-sulfonylamino)-propionic acid methyl ester | 263404-42-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 3-Hydroxy-2-(naphthalene-1-sulfonylamino)-propionic acid methyl ester
• 英文别名: Methyl 3-hydroxy-2-(naphthalen-1-ylsulfonylamino)propanoate
• CAS: 263404-42-8
• 化学式: C₁₄H₁₅NO₅S
• 分子量: 309.343
• InChiKey: YWGLHNDMBVGPJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-Hydroxy-2-(naphthalene-1-sulfonylamino)-propionic acid methyl ester 在 N-氯代丁二酰亚胺 、 sodium hydride 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 methyl (E)-2-(N-naphthalene-1-sulfonylcinnamamido)-3-chloropropanoate
  参考文献：
  名称：

  Desulfonylation of Amides using Tributyltin Hydride, Samarium Diiodide or Zinc/Titanium Tetrachloride. A Comparison of Methods

  摘要：

  Deprotection of N-sulfonylated amides can be achieved by reaction with Bu3SnH, SmI2 or TiCl4/Zn. All three methods gave good yields (typically >60%) when using N-benzoyl or related amides while the corresponding N-acetyl derivatives proved to be inert to deprotection under the same reaction conditions. The mechanistic implications of this are discussed. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00025-9
• 作为产物：
  描述：

  1-萘磺酰氯 、 DL-丝氨酸甲酯盐酸盐 以 吡啶 为溶剂， 生成 3-Hydroxy-2-(naphthalene-1-sulfonylamino)-propionic acid methyl ester
  参考文献：
  名称：

  Desulfonylation of Amides using Tributyltin Hydride, Samarium Diiodide or Zinc/Titanium Tetrachloride. A Comparison of Methods

  摘要：

  Deprotection of N-sulfonylated amides can be achieved by reaction with Bu3SnH, SmI2 or TiCl4/Zn. All three methods gave good yields (typically >60%) when using N-benzoyl or related amides while the corresponding N-acetyl derivatives proved to be inert to deprotection under the same reaction conditions. The mechanistic implications of this are discussed. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00025-9

文献信息

• Desulfonylation of Amides using Tributyltin Hydride, Samarium Diiodide or Zinc/Titanium Tetrachloride. A Comparison of Methods
  作者：Haydn S Knowles、Andrew F Parsons、Robert M Pettifer、Stéphane Rickling

  DOI：10.1016/s0040-4020(00)00025-9

  日期：2000.2

  Deprotection of N-sulfonylated amides can be achieved by reaction with Bu3SnH, SmI2 or TiCl4/Zn. All three methods gave good yields (typically >60%) when using N-benzoyl or related amides while the corresponding N-acetyl derivatives proved to be inert to deprotection under the same reaction conditions. The mechanistic implications of this are discussed. (C) 2000 Elsevier Science Ltd. All rights reserved.