N,N'-dimethyl-N,N'-bis-((3'aR,4'aR)-7'-oxooctahydro-6'a,7'a-diaza-7'-phospha-cyclopenta[a]pentalene-7'-yl)-pentane-1,5-diamine | 372022-35-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: N,N'-dimethyl-N,N'-bis-((3'aR,4'aR)-7'-oxooctahydro-6'a,7'a-diaza-7'-phospha-cyclopenta[a]pentalene-7'-yl)-pentane-1,5-diamine
• 英文别名: N,N'-dimethyl-N,N'-bis-((3'aR,4'bR)-7'-oxooctahydro-6'a,7'a-diaza-7'-phosphacyclopenta[a]pentalene-7'-yl)-pentane-1,5-diamine；N,N'-dimethyl-N,N'-bis((3aR,7aR)-7-oxooctahydro-6a,7a-diaza-7-phospha-cyclopenta[a]pentalen-7-yl)pentane-1,5-diamine；N,N'-dimethyl-N,N'-bis[(1R,2R)-7-oxo-6,8-diaza-7lambda5-phosphatricyclo[6.3.0.02,6]undecan-7-yl]pentane-1,5-diamine；N,N'-dimethyl-N,N'-bis[(1R,2R)-7-oxo-6,8-diaza-7λ5-phosphatricyclo[6.3.0.02,6]undecan-7-yl]pentane-1,5-diamine
• CAS: 372022-35-0
• 化学式: C₂₃H₄₄N₆O₂P₂
• 分子量: 498.589
• InChiKey: GKCOBJYSFNJADZ-SSGKUCQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  53.6
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N,N'-dimethyl-N,N'-bis-((3'aR,4'aR)-7'-oxooctahydro-6'a,7'a-diaza-7'-phospha-cyclopenta[a]pentalene-7'-yl)-pentane-1,5-diamine 、 四氯化锡 以 二氯甲烷 、 正戊烷 为溶剂， 生成
  参考文献：
  名称：

  Understanding the Correlation of Structure and Selectivity in the Chiral-Phosphoramide-Catalyzed Enantioselective Allylation Reactions:  Solution and Solid-State Structural Studies of Bisphosphoramide·SnCl₄ Complexes

  摘要：

  Complexation of bisphosphoramides, linked by various length methylene tethers, with tin tetrachloride was studied by both solution NMR spectroscopy and single-crystal X-ray crystallography. The formation of cis-configured, octahedral 1/1 bisphosphoramide.SnCl4 complexes was supported by both crystallographic and solution NMR studies. In addition, the formation of such complexes was shown to be highly dependent on the tether length and solution concentration. Single-crystal X-ray analysis of bisphosphoramide.SnCl4 complexes also provided detailed information on the stereochemical environment relevant to the enantioselectivity of asymmetric allylation reactions.

  DOI：

  10.1021/ja021280g
• 作为产物：
  描述：

  2,2’-bipyrrolidine 在 正丁基锂 、 L-酒石酸 、 溶剂黄146 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙醚 、 水 为溶剂， 反应 5.0h， 生成 N,N'-dimethyl-N,N'-bis-((3'aR,4'aR)-7'-oxooctahydro-6'a,7'a-diaza-7'-phospha-cyclopenta[a]pentalene-7'-yl)-pentane-1,5-diamine
  参考文献：
  名称：

  手性磷酰胺催化的烯丙基三氯硅烷对醛的对映选择性加成。用二齿磷基酰胺进行的制备性研究

  摘要：

  基于机械学的见解，即对映选择性烯丙基化的速率和立体化学决定步骤涉及多个路易斯基本部分（磷酰胺），开发了二齿手性磷酰胺。通过不同长度的亚甲基链的束缚连接不同的手性磷酰胺部分。发现由二齿磷酰胺促进的与烯丙基三氯硅烷的烯丙基化的速率和对映选择性高度依赖于系链长度。设计了一种新的基于2,2'-双吡咯烷骨架的磷酰胺，在烯丙基化反应中具有良好的收率，有效的转化率和高的对映选择性。对映体纯的2,2'-双吡咯烷的合成很容易通过吡咯烷的光二聚化，然后用四氢呋喃进行拆分而大规模完成。l（或d）酒石酸。用各种取代的烯丙基三氯硅烷和不饱和醛检查了烯丙基化反应的范围。通过添加不对称的γ-二取代的烯丙基三氯硅烷，该方法已应用于立体异构的季中心的构建。

  DOI：

  10.1021/jo052203h
• 作为试剂：
  描述：

  苯甲醛 、 三氯-((e)-3,7-二甲基-2, 6-辛二烯)-硅烷 在 N,N'-dimethyl-N,N'-bis-((3'aR,4'aR)-7'-oxooctahydro-6'a,7'a-diaza-7'-phospha-cyclopenta[a]pentalene-7'-yl)-pentane-1,5-diamine 、 N,N-二异丙基乙胺 、 potassium fluoride 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 以83%的产率得到(1S*,2S*)-2,6-Dimethyl-2-ethenyl-1-phenyl-5-hepten-1-ol
  参考文献：
  名称：

  (R,R)-2,2'-BISPYRROLIDINE AND (S,S)-2,2'-BISPYRROLIDINE: USEFUL LIGANDS FOR ASYMMETRIC SYNTHESIS

  摘要：

  DOI：

  10.15227/orgsyn.083.0121

文献信息

• Catalytic, Enantioselective Addition of Substituted Allylic Trichlorosilanes Using a Rationally-Designed 2,2‘-Bispyrrolidine-Based Bisphosphoramide
  作者：Scott E. Denmark、Jiping Fu

  DOI：10.1021/ja016552e

  日期：2001.9.1
• Chiral Phosphoramide-Catalyzed Enantioselective Addition of Allylic Trichlorosilanes to Aldehydes. Preparative Studies with Bidentate Phosphorus-Based Amides
  作者：Scott E. Denmark、Jiping Fu、Michael J. Lawler

  DOI：10.1021/jo052203h

  日期：2006.2.1

  that more than one Lewis basic moiety (phosphoramide) is involved in the rate- and stereochemistry-determining step of enantioselective allylation, bidentate chiral phosphoramides were developed. Different chiral phosphoramide moieties were connected by tethers of methylene chains of varying length. The rate and enantioselectivity of allylation with allyltrichlorosilane promoted by the bidentate phosphoramides

  基于机械学的见解，即对映选择性烯丙基化的速率和立体化学决定步骤涉及多个路易斯基本部分（磷酰胺），开发了二齿手性磷酰胺。通过不同长度的亚甲基链的束缚连接不同的手性磷酰胺部分。发现由二齿磷酰胺促进的与烯丙基三氯硅烷的烯丙基化的速率和对映选择性高度依赖于系链长度。设计了一种新的基于2,2'-双吡咯烷骨架的磷酰胺，在烯丙基化反应中具有良好的收率，有效的转化率和高的对映选择性。对映体纯的2,2'-双吡咯烷的合成很容易通过吡咯烷的光二聚化，然后用四氢呋喃进行拆分而大规模完成。l（或d）酒石酸。用各种取代的烯丙基三氯硅烷和不饱和醛检查了烯丙基化反应的范围。通过添加不对称的γ-二取代的烯丙基三氯硅烷，该方法已应用于立体异构的季中心的构建。
• Understanding the Correlation of Structure and Selectivity in the Chiral-Phosphoramide-Catalyzed Enantioselective Allylation Reactions:  Solution and Solid-State Structural Studies of Bisphosphoramide·SnCl₄ Complexes
  作者：Scott E. Denmark、Jiping Fu

  DOI：10.1021/ja021280g

  日期：2003.2.1

  Complexation of bisphosphoramides, linked by various length methylene tethers, with tin tetrachloride was studied by both solution NMR spectroscopy and single-crystal X-ray crystallography. The formation of cis-configured, octahedral 1/1 bisphosphoramide.SnCl4 complexes was supported by both crystallographic and solution NMR studies. In addition, the formation of such complexes was shown to be highly dependent on the tether length and solution concentration. Single-crystal X-ray analysis of bisphosphoramide.SnCl4 complexes also provided detailed information on the stereochemical environment relevant to the enantioselectivity of asymmetric allylation reactions.