methyl 2-[N-(2-methylallyl)-N-tosylamino]acetate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2-[N-(2-methylallyl)-N-tosylamino]acetate
• 英文别名: Methyl 2-[(4-methylphenyl)sulfonyl-(2-methylprop-2-enyl)amino]acetate
• 化学式: C₁₄H₁₉NO₄S
• 分子量: 297.375
• InChiKey: YORABFUSJNVMNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  对甲苯磺酰甘氨酸甲酯 、 3-氯-2-甲基丙烯 在 caesium carbonate 作用下， 以 丙酮 为溶剂， 以88%的产率得到methyl 2-[N-(2-methylallyl)-N-tosylamino]acetate
  参考文献：
  名称：

  Intramolecular Cycloaddition of O-tert-Butyldimethylsilyloximes in the Presence of BF₃·OEt₂

  摘要：

  Intramolecular cycloaddition of novel 1,3-dipoles, N-boranonitrones, was examined. Treatment of O-tert-butyldimethylsilyloximes 9-12 having olefin moieties with 2 equiv of BF3 center dot OEt2 generated N-boranonitrones, which underwent intramolecular cycloaddition to afford N-nonsubstituted cycloadducts 16 (and/or 18) after extractive workup. Despite the Lewis-acidic conditions, the olefin geometry of the substrates was retained in the cycloadducts in the present cycloaddition. The electronic nature of the N-boranonitrones appeared to be electrophilic. In the case of substrate 11c, having an electron-donating methyl group at an internal position of the olefin moiety, the cycloaddition gave the bridged cycloadduct 18b. The cycloaddition proceeded at relatively low temperature, and the diastereoselectivity was high.

  DOI：

  10.1021/jo051652e

文献信息

• Intramolecular Cycloaddition of <i>O</i>-<i>tert</i>-Butyldimethylsilyloximes in the Presence of BF₃·OEt₂
  作者：Osamu Tamura、Takahiro Mitsuya、Xin Huang、Yoshiyuki Tsutsumi、Sanae Hattori、Hiroyuki Ishibashi

  DOI：10.1021/jo051652e

  日期：2005.12.1

  Intramolecular cycloaddition of novel 1,3-dipoles, N-boranonitrones, was examined. Treatment of O-tert-butyldimethylsilyloximes 9-12 having olefin moieties with 2 equiv of BF3 center dot OEt2 generated N-boranonitrones, which underwent intramolecular cycloaddition to afford N-nonsubstituted cycloadducts 16 (and/or 18) after extractive workup. Despite the Lewis-acidic conditions, the olefin geometry of the substrates was retained in the cycloadducts in the present cycloaddition. The electronic nature of the N-boranonitrones appeared to be electrophilic. In the case of substrate 11c, having an electron-donating methyl group at an internal position of the olefin moiety, the cycloaddition gave the bridged cycloadduct 18b. The cycloaddition proceeded at relatively low temperature, and the diastereoselectivity was high.