(1S,2S)-1,2-diphenyl-N-ethoxycarbonylethylenediamine | 203922-97-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (1S,2S)-1,2-diphenyl-N-ethoxycarbonylethylenediamine
• 英文别名: ethyl N-[(1S,2S)-2-amino-1,2-diphenylethyl]carbamate
• CAS: 203922-97-8
• 化学式: C₁₇H₂₀N₂O₂
• 分子量: 284.358
• InChiKey: FQQSWGLDUGTCEO-HOTGVXAUSA-N

物化性质

• 沸点：
  443.8±45.0 °C(Predicted)
• 密度：
  1.137±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  64.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,2S)-1,2-diphenyl-N-ethoxycarbonylethylenediamine 在 2-chloro-1,3-dimethyl imidazolium chloride 、 四丁基氟化铵 、 sodium methylate 、 甲基磺酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 131.0h， 生成 (2S,3S,7S,8S)-2,3,7,8-tetraphenyl-1,4,6-triazabicyclo[3.3.0]oct-4-ene
  参考文献：
  名称：

  胍催化羰基化合物的不对称三甲基甲硅烷基氰化

  摘要：

  几种改性的胍被用于3-苯基丙醛，环己烷甲醛，新戊醛和4-苯基-2-丁酮的三甲基甲硅烷基氰化反应。当C 2对称的双环胍，（2 S，3 S，7 S，8 S）-四苯基-1,4,8-三氮杂[2.2.0]时，即使在酮底物上也获得了良好至中等的对映选择性。双环辛-4-烯用作基础催化剂。

  DOI：

  10.1002/adsc.200505161
• 作为产物：
  描述：

  (1S,2S)-1,2-二苯基乙二胺 、 氯甲酸乙酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以74%的产率得到(1S,2S)-1,2-diphenyl-N-ethoxycarbonylethylenediamine
  参考文献：
  名称：

  Modified Guanidines as Potential Chiral Superbases. 2. Preparation of 1,3-Unsubstituted and 1-Substituted 2-Iminoimidazolidine Derivatives and a Related Guanidine by the 2-Chloro-1,3-dimethylimidazolinium Chloride-Induced Cyclization of Thioureas

  摘要：

  Simple preparation methods for modified guanidines were explored for new chiral superbases, Thus, (4S,5S)-4,5-diphenyl- and diastereomeric cyclohexane-fused 2-iminoimidazolidines were prepared from (1S,2S)-1,2-diphenylethylenediamine and (1R,2R)- or (1S,2S)-1,2-diaminocyclohexanes through cyclization of protected thiourea intermediates with 2-chloro-1,3-dimethylimidazolinium chloride (DMC) as a key reaction. In the (4S,SS)-4,5-diphenyl series 1-methyl-2-iminoimidazolidines and 2-diethylaminoimidazoline were also prepared as related guanidines.

  DOI：

  10.1021/jo000745n

文献信息

• Modified Guanidines as Potential Chiral Superbases. 3. Preparation of 1,4,6-Triazabicyclooctene Systems and 1,4-Disubstituted 2-Iminoimidazolidines by the 2-Chloro-1,3-dimethylimidazolinium Chloride-Induced Cyclization of Guanidines with a Hydroxyethyl Substituent
  作者：Toshio Isobe、Keiko Fukuda、Kentaro Yamaguchi、Hiroko Seki、Tatsuhiro Tokunaga、Tsutomu Ishikawa

  DOI：10.1021/jo000746f

  日期：2000.11.1

  Simple preparation methods of modified guanidines have been explored as potential chiral superbases. Thus, 3,7,8-trisubstituted and 3,6,7,8-tetrasubstituted 1,4,6-triazabicyclooctene systems were prepared from (1S,2S)-1,2-diphenylethylenediamine through stepwise 2-chloro-1,3-dimethylimidazolinium chloride (DMC)-induced cyclizations of protected thioureas to the corresponding 2-iminoimidazolidines and then of 2-(2-hydroxyethylimino)imidazolidines to the bicyclic systems. Linear guanidines with a 2-hydroxyethyl functional group were prepared by the reaction of carbodiimides with 2-amino alcohols. Reaction of linear-type guanidines with DMC followed by base treatment afforded 1,4-disubstitued 2-iminoimidazolidines. Furthermore, another type of 1,4,6-triazabicyclooctene was also prepared through double DMC-induced cyclization of guanidines with two a-hydroxyethyl substituents.
• Guanidine-Catalyzed Asymmetric Trimethylsilylcyanation of Carbonyl Compounds
  作者：Yukari Kitani、Takuya Kumamoto、Toshio Isobe、Keiko Fukuda、Tsutomu Ishikawa

  DOI：10.1002/adsc.200505161

  日期：2005.10

  Several kinds of modified guanidines were applied to the trimethylsilylcyanation of 3-phenylpropanal, cylohexanecarboxaldehyde, pivalaldehyde, and 4-phenyl-2-butanone. Good to moderate enantioselectivity was obtained, even on a ketonic substrate, when a C2-symmetrical bicyclic guanidine, (2S,3S,7S,8S)-tetraphenyl-1,4,8-triaza[2.2.0]bicyclooct-4-ene, was used as a base catalyst.

  几种改性的胍被用于3-苯基丙醛，环己烷甲醛，新戊醛和4-苯基-2-丁酮的三甲基甲硅烷基氰化反应。当C 2对称的双环胍，（2 S，3 S，7 S，8 S）-四苯基-1,4,8-三氮杂[2.2.0]时，即使在酮底物上也获得了良好至中等的对映选择性。双环辛-4-烯用作基础催化剂。
• Modified Guanidines as Potential Chiral Superbases. 2. Preparation of 1,3-Unsubstituted and 1-Substituted 2-Iminoimidazolidine Derivatives and a Related Guanidine by the 2-Chloro-1,3-dimethylimidazolinium Chloride-Induced Cyclization of Thioureas
  作者：Toshio Isobe、Keiko Fukuda、Tatsuhiro Tokunaga、Hiroko Seki、Kentaro Yamaguchi、Tsutomu Ishikawa

  DOI：10.1021/jo000745n

  日期：2000.11.1

  Simple preparation methods for modified guanidines were explored for new chiral superbases, Thus, (4S,5S)-4,5-diphenyl- and diastereomeric cyclohexane-fused 2-iminoimidazolidines were prepared from (1S,2S)-1,2-diphenylethylenediamine and (1R,2R)- or (1S,2S)-1,2-diaminocyclohexanes through cyclization of protected thiourea intermediates with 2-chloro-1,3-dimethylimidazolinium chloride (DMC) as a key reaction. In the (4S,SS)-4,5-diphenyl series 1-methyl-2-iminoimidazolidines and 2-diethylaminoimidazoline were also prepared as related guanidines.