N-nitroso-N-(trans-2-methylcyclopropyl)urea

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: N-nitroso-N-(trans-2-methylcyclopropyl)urea
• 英文别名: trans-(2-Methylcyclopropyl)-N-nitrosoharnstoff；N-Nitroso-N--harnstoff；1-[(1R,2R)-2-methylcyclopropyl]-1-nitrosourea
• 化学式: C₅H₉N₃O₂
• 分子量: 143.145
• InChiKey: QJCRIDRQNRUDDP-QWWZWVQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  75.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  甲醇 、 N-nitroso-N-(trans-2-methylcyclopropyl)urea 在 碳酸氢钠 作用下， 反应 2.0h， 生成 1-甲氧基丁-2-烯 、 3-methoxybut-1-ene
  参考文献：
  名称：

  Deamination of trans-2-Methyl- and trans-2-Phenylcyclopropylamines

  摘要：

  The deaminations of trans-2-methyl- and 2-phenylcyclopropylamine hydrochlorides in acetic acid solution have been examined. A major product in each case was an allylic chloride, and the amount of chlorides increased when the chloride ion concentration was increased, With the methyl-substituted amine, increasing the chloride ion concentration changed the major chloride product from crotyl chloride to methallyl chloride. The addition of lithium perchlorate led to a reduction in the amount of chlorides formed. These results indicate that an ion pair is involved in the reaction. The deamination of the related open chain amines gave only small amounts of chlorides, B3LYP/6-31G* calculations found cyclopropyldazonium chloride to prefer to have the chloride ion over the cyclopropyl ring. The transition state was located, and when followed down to products, allyl chloride was found. Similar calculations for the methyl-substituted series led to crotyl chloride from the ion pair with one chloride ion and to methallyl chloride from the ion-tripler with two chloride ions. The deaminations of the corresponding nitrosoureas in basic methanol also were studied. The products were the expected ethers. The addition of azide ion led to azides that were largely formed by initial reaction with the diazonium ion to give a pentazene that lost nitrogen to give the azide. However, some of the azide was formed by an S(N)2 displacement.

  DOI：

  10.1021/jo9906532
• 作为产物：
  描述：

  trans-2-methylcyclopropylurea 在 乙酸酐 、 溶剂黄146 、 sodium nitrite 作用下， 生成 N-nitroso-N-(trans-2-methylcyclopropyl)urea
  参考文献：
  名称：

  Kirmse,W.; Urbach,H., Chemische Berichte, 1972, vol. 105, p. 832 - 839

  摘要：

  DOI：

文献信息

• Kirmse,W.; Seipp,U., Chemische Berichte, 1974, vol. 107, p. 745 - 758
  作者：Kirmse,W.、Seipp,U.

  DOI：——

  日期：——
• Deamination of <i>trans</i>-2-Methyl- and <i>trans</i>-2-Phenylcyclopropylamines
  作者：Kenneth B. Wiberg、Carmen G. Österle

  DOI：10.1021/jo9906532

  日期：1999.10.1

  The deaminations of trans-2-methyl- and 2-phenylcyclopropylamine hydrochlorides in acetic acid solution have been examined. A major product in each case was an allylic chloride, and the amount of chlorides increased when the chloride ion concentration was increased, With the methyl-substituted amine, increasing the chloride ion concentration changed the major chloride product from crotyl chloride to methallyl chloride. The addition of lithium perchlorate led to a reduction in the amount of chlorides formed. These results indicate that an ion pair is involved in the reaction. The deamination of the related open chain amines gave only small amounts of chlorides, B3LYP/6-31G* calculations found cyclopropyldazonium chloride to prefer to have the chloride ion over the cyclopropyl ring. The transition state was located, and when followed down to products, allyl chloride was found. Similar calculations for the methyl-substituted series led to crotyl chloride from the ion pair with one chloride ion and to methallyl chloride from the ion-tripler with two chloride ions. The deaminations of the corresponding nitrosoureas in basic methanol also were studied. The products were the expected ethers. The addition of azide ion led to azides that were largely formed by initial reaction with the diazonium ion to give a pentazene that lost nitrogen to give the azide. However, some of the azide was formed by an S(N)2 displacement.
• Kirmse,W.; Urbach,H., Chemische Berichte, 1972, vol. 105, p. 832 - 839
  作者：Kirmse,W.、Urbach,H.

  DOI：——

  日期：——