N-[(3,3-dimethyloxiran-2-yl)methyl]-4-methoxybenzenesulfonamide | 1369589-53-6

• 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-[(3,3-dimethyloxiran-2-yl)methyl]-4-methoxybenzenesulfonamide
• CAS: 1369589-53-6
• 化学式: C₁₂H₁₇NO₄S
• 分子量: 271.337
• InChiKey: YFNATZRDEDYHNG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  76.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[(3,3-dimethyloxiran-2-yl)methyl]-4-methoxybenzenesulfonamide 、 苯胺 在 tungsten hexa-ethoxide 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以51%的产率得到N-(2-hydroxy-3-methyl-3-(phenylamino)butyl)-4-methoxybenzenesulfonamide
  参考文献：
  名称：

  Tungsten-Catalyzed Regioselective and Stereospecific Ring Opening of 2,3-Epoxy Alcohols and 2,3-Epoxy Sulfonamides

  摘要：

  The first catalytic, highly C3-selective, stereosepecific ring-opening reaction of 2,3-epoxy alcohols and 2,3-epoxy sulfonamides has been accomplished. This process was efficiently promoted by W-salts, and the developed method was applicable to various epoxides with diverse N- and O-nucleophiles affording the products in good to excellent yields (up to 95%) and generally with high regioselectivities (C3:C2 up to >99:1).

  DOI：

  10.1021/ja5029809
• 作为产物：
  描述：

  4-methoxy-N-(3-methylbut-2-enyl)benzenesulfonamide 在 4-二甲氨基吡啶 、 C₆₈H₇₄N₆O₁₃ 、 双氧水 、 magnesium sulfate 、 N,N'-二异丙基碳二亚胺 作用下， 以 氯仿 、 水 为溶剂， 反应 72.0h， 以96%的产率得到N-[(3,3-dimethyloxiran-2-yl)methyl]-4-methoxybenzenesulfonamide
  参考文献：
  名称：

  橙胺和香叶胺衍生物的催化剂控制的位点选择性不对称环氧化

  摘要：

  已经开发了用于神经胺和香叶胺衍生物的位和对映选择性环氧化的新型催化剂。虽然米CPBA氧化发生在选择性越富电子的双键，得到6,7-环氧化物，这些催化剂提供2,3-环氧化物在中度到高对映选择性通过的相对缺电子的双键的氧化。

  DOI：

  10.1039/c7cc04809b

文献信息

• Hf(IV)-Catalyzed Enantioselective Epoxidation of <i>N</i>-Alkenyl Sulfonamides and <i>N</i>-Tosyl Imines
  作者：José Luis Olivares-Romero、Zhi Li、Hisashi Yamamoto

  DOI：10.1021/ja211880s

  日期：2012.3.28

  Asymmetric epoxidation of allylic and homoallylic amine derivatives catalyzed by Hf(IV)-bishydroxamic acid complexes is described. Under similar conditions, aldimine and ketimine produced oxaziridines. The sulfonyl group is demonstrated to be an effective directing group for these transformations.

  描述了由 Hf (IV)-双异羟肟酸配合物催化的烯丙基和高烯丙基胺衍生物的不对称环氧化。在相似的条件下，醛亚胺和酮亚胺生成恶氮丙啶。磺酰基被证明是这些转化的有效导向基团。
• Tungsten-Catalyzed Regioselective and Stereospecific Ring Opening of 2,3-Epoxy Alcohols and 2,3-Epoxy Sulfonamides
  作者：Chuan Wang、Hisashi Yamamoto

  DOI：10.1021/ja5029809

  日期：2014.5.14

  The first catalytic, highly C3-selective, stereosepecific ring-opening reaction of 2,3-epoxy alcohols and 2,3-epoxy sulfonamides has been accomplished. This process was efficiently promoted by W-salts, and the developed method was applicable to various epoxides with diverse N- and O-nucleophiles affording the products in good to excellent yields (up to 95%) and generally with high regioselectivities (C3:C2 up to >99:1).
• Catalyst-controlled site-selective asymmetric epoxidation of nerylamine and geranylamine derivatives
  作者：Tomoya Nobuta、Takeo Kawabata

  DOI：10.1039/c7cc04809b

  日期：——

  Novel catalysts for site- and enantioselective epoxidation of nerylamine and geranylamine derivatives have been developed. Although mCPBA oxidation took place selectively at the more electron-rich double bond to give the 6,7-epoxides, these catalysts provide the 2,3-epoxides in moderate to high enantioselectivity via the oxidation of the relatively electron-deficient double bond.

  已经开发了用于神经胺和香叶胺衍生物的位和对映选择性环氧化的新型催化剂。虽然米CPBA氧化发生在选择性越富电子的双键，得到6,7-环氧化物，这些催化剂提供2,3-环氧化物在中度到高对映选择性通过的相对缺电子的双键的氧化。