(1S,3R,8R,11R,12R)-10-oxo-2,9-diazatetracyclo[10.2.2.0(2,11).0(3,8)]hexadec-13-ene | 1423018-69-2

• 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: (1S,3R,8R,11R,12R)-10-oxo-2,9-diazatetracyclo[10.2.2.0(2,11).0(3,8)]hexadec-13-ene
• 英文别名: (1S,3R,8R,11R,12R)-2,9-diazatetracyclo[10.2.2.02,11.03,8]hexadec-13-en-10-one
• CAS: 1423018-69-2
• 化学式: C₁₄H₂₀N₂O
• 分子量: 232.326
• InChiKey: DVMHGFODWSSAOY-ZOLYEBIHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,3R,8R,11R,12R)-10-oxo-2,9-diazatetracyclo[10.2.2.0(2,11).0(3,8)]hexadec-13-ene 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 24.0h， 以45%的产率得到(3R,8R,11R)-10-oxo-2,9-diazatetracyclo[10.2.2.0^2.11.0^3.8]hexadecane
  参考文献：
  名称：

  Autoxidation of a tetracyclic lactam and its conversion to an enantiopure tertiary alcohol

  摘要：

  The reduction of chiral tetracyclic lactams 1,2 led to new functionalized derivatives 5-8 containing 3 or 5 stereogenic centers. Autoxidation of compound 5 was observed yielding an enantiopure peroxide 9, which in turn slowly converted into tertiary alcohol 10. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.08.001
• 作为产物：
  描述：

  1,3-环己二烯 、 乙醛酸乙酯 、 (1R,2R)-1,2-diaminocyclohexane 在 三氟化硼乙醚 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 22.0h， 以2.7 g的产率得到(1S,3R,8R,11R,12R)-10-oxo-2,9-diazatetracyclo[10.2.2.0(2,11).0(3,8)]hexadec-13-ene
  参考文献：
  名称：

  Monoimine Derived from trans-1,2-Diaminocyclohexane and Ethyl Glyoxylate: An Intermediate in Aza-Diels–Alder and Mannich Reactions

  摘要：

  Novel enantiopure policyclic nitrogen heterocycles have been obtained in the diastereoselective aza-Diels-Alder or Mannich reaction of dienes with imine formed in situ from ethyl glyoxylate and (1R,2R)-diaminocyclohexane.

  DOI：

  10.1021/jo302820m

文献信息

• Monoimine Derived from <i>trans</i>-1,2-Diaminocyclohexane and Ethyl Glyoxylate: An Intermediate in Aza-Diels–Alder and Mannich Reactions
  作者：Elżbieta Wojaczyńska、Julia Bąkowicz、Mateusz Dorsz、Jacek Skarżewski

  DOI：10.1021/jo302820m

  日期：2013.3.15

  Novel enantiopure policyclic nitrogen heterocycles have been obtained in the diastereoselective aza-Diels-Alder or Mannich reaction of dienes with imine formed in situ from ethyl glyoxylate and (1R,2R)-diaminocyclohexane.
• Autoxidation of a tetracyclic lactam and its conversion to an enantiopure tertiary alcohol
  作者：Elżbieta Wojaczyńska、Ilona Turowska-Tyrk

  DOI：10.1016/j.tetasy.2013.08.001

  日期：2013.10

  The reduction of chiral tetracyclic lactams 1,2 led to new functionalized derivatives 5-8 containing 3 or 5 stereogenic centers. Autoxidation of compound 5 was observed yielding an enantiopure peroxide 9, which in turn slowly converted into tertiary alcohol 10. (C) 2013 Elsevier Ltd. All rights reserved.