tert-butyl N-[(2E)-penta-2,4-dienyl]-N-prop-2-ynoxycarbamate | 1443059-13-9

• 分子结构分类: 有机化合物 - 乙炔化物 - 碳化物
• 英文名称: tert-butyl N-[(2E)-penta-2,4-dienyl]-N-prop-2-ynoxycarbamate
• CAS: 1443059-13-9
• 化学式: C₁₃H₁₉NO₃
• 分子量: 237.299
• InChiKey: DWNSXIPNLSPZCY-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(2E)-penta-2,4-dienyl]-N-prop-2-ynoxycarbamate 在 bis(1,5-cyclooctadiene)nickel (0) 、 samarium diiodide 、 三苯基膦 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 6.0h， 生成 ethyl 2-[4-[[hydroxy-[(2-methylpropan-2-yl)oxycarbonyl]amino]methyl]-3-methylidenecyclonona-1,5-dien-1-yl]acetate
  参考文献：
  名称：

  Synthesis of monocyclic nine-membered compounds by the [4+3+2] cycloaddition-bond cleavage strategy

  摘要：

  Monocyclic nine-membered compounds were synthesized by the cleavage of the six-membered ring of the bicyclic compounds. Thus, the bicyclic compounds which consist of six- and nine-membered rings were synthesized by the Ni-catalyzed [4+3+2] cycloaddition, and the cleavage of the N-O bond, which was incorporated in the six-membered ring, proceeded in the presence of Mo(CO)(6) to yield the monocyclic compound. On the other hand, the cleavage of the C-O bond proceeded efficiently in the presence of SmI2. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.04.094
• 作为产物：
  描述：

  tert-butyl (prop-2-yn-1-yloxy)carbamate 、 (E)-5-bromopenta-1,3-diene 在 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 3.41h， 以67%的产率得到tert-butyl N-[(2E)-penta-2,4-dienyl]-N-prop-2-ynoxycarbamate
  参考文献：
  名称：

  Synthesis of monocyclic nine-membered compounds by the [4+3+2] cycloaddition-bond cleavage strategy

  摘要：

  Monocyclic nine-membered compounds were synthesized by the cleavage of the six-membered ring of the bicyclic compounds. Thus, the bicyclic compounds which consist of six- and nine-membered rings were synthesized by the Ni-catalyzed [4+3+2] cycloaddition, and the cleavage of the N-O bond, which was incorporated in the six-membered ring, proceeded in the presence of Mo(CO)(6) to yield the monocyclic compound. On the other hand, the cleavage of the C-O bond proceeded efficiently in the presence of SmI2. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.04.094

文献信息

• Synthesis of monocyclic nine-membered compounds by the [4+3+2] cycloaddition-bond cleavage strategy
  作者：Ryu Yamasaki、Korehito Kato、Daichi Hanitani、Yuichiro Mutoh、Shinichi Saito

  DOI：10.1016/j.tetlet.2013.04.094

  日期：2013.7

  Monocyclic nine-membered compounds were synthesized by the cleavage of the six-membered ring of the bicyclic compounds. Thus, the bicyclic compounds which consist of six- and nine-membered rings were synthesized by the Ni-catalyzed [4+3+2] cycloaddition, and the cleavage of the N-O bond, which was incorporated in the six-membered ring, proceeded in the presence of Mo(CO)(6) to yield the monocyclic compound. On the other hand, the cleavage of the C-O bond proceeded efficiently in the presence of SmI2. (c) 2013 Elsevier Ltd. All rights reserved.