(1S,2R)-1-N,1-N,2-N,2-N-四甲基环戊烷-1,2-二胺 | 89121-43-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: (1S,2R)-1-N,1-N,2-N,2-N-四甲基环戊烷-1,2-二胺
• 英文名称: cis-N,N,N',N'-tetramethyl-1,2-diaminocyclopentane
• 英文别名: cis-N,N,N',N'-tetramethylcyclopentane-1,2-diamine；cis-1,2-bis(N,N-dimethylamino)cyclopentane；(1S,2R)-1-N,1-N,2-N,2-N-tetramethylcyclopentane-1,2-diamine
• CAS: 89121-43-7
• 化学式: C₉H₂₀N₂
• 分子量: 156.271
• InChiKey: AROKCSAMRXQWCD-DTORHVGOSA-N

物化性质

• 沸点：
  40 °C(Press: 0.8 Torr)
• 密度：
  0.90±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  顺式-1,2-环戊烷二胺 生成 (1S,2R)-1-N,1-N,2-N,2-N-四甲基环戊烷-1,2-二胺
  参考文献：
  名称：

  Efficient one-step synthesis of a cis vicinal tertiary diamine and its complexation to a lithium carbanion salt

  摘要：

  DOI：

  10.1021/jo00181a047

文献信息

• Efficient preparation of cis vicinal tertiary diamines from 2-hydroxy ketones in two steps
  作者：Gideon Fraenkel、Judith Gallucci、Howard S. Rosenzweig

  DOI：10.1021/jo00264a031

  日期：1989.2
• Cyclic cis vicinal tertiary diamines: structure, conformational dynamics, and proton transfer
  作者：Gideon Fraenkel、Vaidyanathan Balasubramanian、Hyejin Lisa Chang、Judith Gallucci

  DOI：10.1021/ja00068a042

  日期：1993.7

  Carbon-13 NMR line-shape analysis of several cyclic (cyclohexenes and cyclopentanes) cis vicinal tertiary diamines with N-piperidino or N-pyrrolidino substituents reveals barriers to cyclohexane inversion (DELTAH(double dagger)) of 10-11 kcal/mol with DELTAS(double dagger) = 6-8 eu, while for piperidine inversion DELTAH(double dagger) = 10-12 kcal/mol with a DELTAS(double dagger) of 2-9 eu. All cis diamines studied exhibited two pK(a)'s, the first 10-11 and the second 3-5. The crystal structure of cis-1,2-bis(N,N-dimethylamino)cyclopentane monopicrate, I-picrate, shows the diamine, 1, to bc unsymmetrically protonated, the acid proton-nitrogen distances being 2.56 and 0.93 angstrom; the entire assembly of O-(picrate), acid proton, and two nitrogens is almost coplanar, with H+ just 0.04 angstrom out of the O-(picrate), N, N+ plane. The cyclopentane forms a half-chair in which the carbons C-N+ and C-N lie, respectively, 0.32 and 0.28 angstrom on opposite sides of the three-methylene-carbon plane. Carbon-13 NMR of several salts of 1 in CD2Cl2 shows that proton transfer between nitrogens within the cation is fast down to 200 K, while reversible transfer of this proton to counterion is much slower. Activation parameters for nitrogen inversion in the monotrifluoroacetate of 9, found from C-13 NMR line-shape analysis to be DELTAH(double dagger) = 22 kcal/mol and DELTAS(double dagger) = 34 eu, imply that fast reversible transfer of a proton between cation and anion is rate determining to nitrogen inversion.
• FRAENKEL, GIDEON;GALLUCCI, JUDITH;ROSENZWEIG, HOWARD S., J. ORG. CHEM., 54,(1989) N, C. 677-681
  作者：FRAENKEL, GIDEON、GALLUCCI, JUDITH、ROSENZWEIG, HOWARD S.

  DOI：——

  日期：——
• FRAENKEL, G.;PRAMANIK, PRADIP, J. ORG. CHEM., 1984, 49, N 7, 1314-1316
  作者：FRAENKEL, G.、PRAMANIK, PRADIP

  DOI：——

  日期：——
• US4078019A
  申请人：——

  公开号：US4078019A

  公开（公告）日：1978-03-07