(S)-N,N'-bis(tert-butoxycarbonyl)-1,2-propanediamine | 185854-57-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 甲亚胺酸及其衍生物
• 英文名称: (S)-N,N'-bis(tert-butoxycarbonyl)-1,2-propanediamine
• 英文别名: tert-butyl N-[(2S)-1-[(2-methylpropan-2-yl)oxycarbonylamino]propan-2-yl]carbamate
• CAS: 185854-57-3
• 化学式: C₁₃H₂₆N₂O₄
• 分子量: 274.36
• InChiKey: FDZFJIXCGHZLKK-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-(-)-α-methoxyphenylacetyl chloride 、 (S)-N,N'-bis(tert-butoxycarbonyl)-1,2-propanediamine 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成
  参考文献：
  名称：

  Diastereo- and Enantioselective Synthesis of Vicinal Diamines via Aza-Michael Addition to Nitroalkenes

  摘要：

  (-)-(2S,3R,4R,5S)-1-氨基-3,4-二甲氧基-2,5-双(甲氧基甲基)的氮杂类似迈克尔加成不对称合成受保护的1,2-二胺4描述了吡咯烷 (ADMP) 转化为硝基烯烃 1 的总收率良好且对映体过量 (ee = 93-96%)。该助剂构成氨的新型手性等价物，并在雷尼镍的还原性 N-N 键断裂下被去除，这也还原了硝基。绝对构型通过核磁共振波谱方法和旋光测定法测定。

  DOI：

  10.1055/s-1996-4411
• 作为产物：
  描述：

  (S)-1-(tert-butoxycarbonyl)-4-methyl-2-phenylimidazoline 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 80.0 ℃ 、5.07 MPa 条件下， 反应 36.17h， 生成 (S)-N,N'-bis(tert-butoxycarbonyl)-1,2-propanediamine
  参考文献：
  名称：

  Catalytic Asymmetric Hydrogenation of N-Boc-Imidazoles and Oxazoles

  摘要：

  Substituted imidazoles and oxazoles were respectively hydrogenated into the corresponding chiral imidazolines and oxazolines (up to 99% ee). The highly enantioselective hydrogenation was achieved by using the chiral ruthenium catalyst, which is generated from Ru(eta(3)-methallyl)(2)(cod) and a trans-chelating chiral bisphosphine ligand, PhTRAP. This is the first successful catalytic asymmetric reduction of 5-membered aromatic rings containing two or more heteroatoms.

  DOI：

  10.1021/ja201543h

文献信息

• Catalytic Asymmetric Hydrogenation of N-Boc-Imidazoles and Oxazoles
  作者：Ryoichi Kuwano、Nao Kameyama、Ryuhei Ikeda

  DOI：10.1021/ja201543h

  日期：2011.5.18

  Substituted imidazoles and oxazoles were respectively hydrogenated into the corresponding chiral imidazolines and oxazolines (up to 99% ee). The highly enantioselective hydrogenation was achieved by using the chiral ruthenium catalyst, which is generated from Ru(eta(3)-methallyl)(2)(cod) and a trans-chelating chiral bisphosphine ligand, PhTRAP. This is the first successful catalytic asymmetric reduction of 5-membered aromatic rings containing two or more heteroatoms.
• Diastereo- and Enantioselective Synthesis of Vicinal Diamines via Aza-Michael Addition to Nitroalkenes
  作者：Dieter Enders、Jürgen Wiedemann

  DOI：10.1055/s-1996-4411

  日期：1996.12

  The asymmetric synthesis of protected 1,2-diamines 4 by aza-analogous Michael addition of (-)-(2S,3R,4R,5S)-1-amino-3,4-dimethoxy-2,5-bis(methoxymethyl)pyrrolidine (ADMP) to nitroalkenes 1 in good overall yields and high enantiomeric excesses (ee = 93-96%) is described. The auxiliary constitutes a novel chiral equivalent of ammonia and is removed under reductive N-N bond cleavage with Raney nickel, which also reduces the nitro group. The absolute configuration was determined by NMR-spectroscopic methods and polarimetry.

  (-)-(2S,3R,4R,5S)-1-氨基-3,4-二甲氧基-2,5-双(甲氧基甲基)的氮杂类似迈克尔加成不对称合成受保护的1,2-二胺4描述了吡咯烷 (ADMP) 转化为硝基烯烃 1 的总收率良好且对映体过量 (ee = 93-96%)。该助剂构成氨的新型手性等价物，并在雷尼镍的还原性 N-N 键断裂下被去除，这也还原了硝基。绝对构型通过核磁共振波谱方法和旋光测定法测定。