2-[N-(2-methylallyl)-N-tosylamino]acetaldehyde O-tert-butyldimethylsilyloxime | 873692-58-1

• 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: 2-[N-(2-methylallyl)-N-tosylamino]acetaldehyde O-tert-butyldimethylsilyloxime
• 英文别名: N-(2-(((tert-butyldimethylsilyl)oxy)imino)ethyl)-4-methyl-N-(2-methylallyl)benzenesulfonamide；N-[2-[tert-butyl(dimethyl)silyl]oxyiminoethyl]-4-methyl-N-(2-methylprop-2-enyl)benzenesulfonamide
• CAS: 873692-58-1
• 化学式: C₁₉H₃₂N₂O₃SSi
• 分子量: 396.626
• InChiKey: LDFAUNJBQAWYLD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.57
• 重原子数：
  26.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  58.97
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-[N-(2-methylallyl)-N-tosylamino]acetaldehyde O-tert-butyldimethylsilyloxime 在 三氟化硼乙醚 作用下， 生成 (1RS,5SR)-5-methyl-3-tosyl-3,7-diaza-6-oxabicyclo[3.2.1]octane
  参考文献：
  名称：

  Intermolecular Cycloaddition of N-Boranonitrone with Alkenes

  摘要：

  Ethyl glyoxylate O-tert-butyldimethylsilyloxime (8), on treatment with 2.2 equiv of BF3 center dot OEt2, generated N-boranonitrone E, which underwent intermolecular cycloaddition with alkenes 18 to afford isoxazolidines 19 in moderate to high yields. The cycloaddition of N-boranonitrone E with most of the alkenes gave 3,5-trans isoxazolidines as the major isomers via a concerted mechanism. However, in the case of 1-methylated cyclic alkenes (18j and 18l), the cycloaddition surprisingly furnished the 3,3a-cis-cycloadducts (19j and 19l) as major isomers. A possible explanation is that the reaction of 1-methylated cyclic alkenes proceeds mainly via a stepwise mechanism. This reaction of terminal alkenes is very useful for synthesis of 1,3-anti aminoalcohol derivatives by reductive cleavage of an N - O bond.

  DOI：

  10.1021/jo800878p
• 作为产物：
  描述：

  N-(2,2-dimethoxyethyl)-2-methyl-N-tosylprop-2-en-1-amine 在 咪唑 、 盐酸 、 盐酸羟胺 、 sodium acetate 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 5.0h， 生成 2-[N-(2-methylallyl)-N-tosylamino]acetaldehyde O-tert-butyldimethylsilyloxime
  参考文献：
  名称：

  引入氰基，酰基和氨基烷基的钴催化环化

  摘要：

  描述了在钴催化下利用C C，C O和C N键有效合成碳环和杂环的方法。烯烃上的取代基是控制初始氢原子转移步骤中区域和化学选择性的关键，并且在温和条件下可以有效地构建季碳。环丙烷裂解和串联环化可在一次操作中得到高度官能化的双环骨架。

  DOI：

  10.1039/c9ob00637k

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.