(1R)-N-nopylpyrrolidine | 132410-33-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R)-N-nopylpyrrolidine
• 英文别名: N-nopylpyrrolidine；1-[2-((1R)-6,6-dimethyl-norpin-2-en-2-yl)-ethyl]-pyrrolidine；1-[2-((1R)-6,6-Dimethyl-norpin-2-en-2-yl)-aethyl]-pyrrolidin；1-[2-[(1R,5S)-6,6-dimethyl-2-bicyclo[3.1.1]hept-2-enyl]ethyl]pyrrolidine
• CAS: 132410-33-4
• 化学式: C₁₅H₂₅N
• 分子量: 219.37
• InChiKey: CQJDGGXCPSOPAL-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1R)-N-nopylpyrrolidine 在 palladium on activated charcoal 、 乙醇 作用下， 100.0 ℃ 、6.86 MPa 条件下， 生成 1-[2-((1S,2X)-6,6-dimethyl-norpinan-2-yl)-ethyl]-pyrrolidine
  参考文献：
  名称：

  The Reaction of Formaldehyde and Secondary Amines with Some Olefins

  摘要：

  DOI：

  10.1021/ja01622a057
• 作为产物：
  描述：

  (1R)6,6-二甲基联环(3.1.1)庚烷-2-烯-2-乙醇 以 四氢呋喃 、 吡啶 为溶剂， 反应 14.0h， 生成 (1R)-N-nopylpyrrolidine
  参考文献：
  名称：

  连接的硼烷的均相反应。第18部分。在极性反转催化条件下，通过手性胺-硼自由基进行对映选择性氢原子抽象以进行动力学拆分的范围

  摘要：

  多种新的和先前已知的旋光胺-硼烷络合物已被用作极性反转催化剂，用于动力学拆分代表性的外消旋含羰基化合物。的关键的步骤涉及由氢原子转移源自催化剂的光学活性胺的氧硼基团从一个C-H键α的羰基官能团的氢的对映选择性抽象叔由二的光解产生的自由基-butoxyl叔正丁基过氧化物。尽管在–74°C的环氧乙烷溶液中，对映体选择性高达8.8，但手性分辨力通常并不大。通常可以通过考虑以非对映异构过渡态连接到硼原子和α-碳原子上的取代基之间的空间相互作用来预测反应性更高的底物对映异构体。但是，氢键和偶极-偶极相互作用以及立体电子效应，也可能在确定对映选择性中起作用，特别是在反应中心周围没有明显的空间不对称性的情况下。

  DOI：

  10.1039/p19940001033

文献信息

• Asymmetric reductions of prochiral ketones with lithium [2-[2-benzyloxy)ethyl]-6,6-dimethylbicyclo[3.1.1]-3-nonyl]-9-boratabicyclo-[3.3.1]nonane (lithium NB-Enantride) and its derivatives
  作者：M. Mark Midland、Aleksander Kazubski、Richard E. Woodling

  DOI：10.1021/jo00003a030

  日期：1991.2

  NB-Enantride, prepared by hydroboration of nopyl benzyl ether with 9-borabicyclo[3.3.1]nonane (9-BBN) followed by treatment with tert-butyllithium, is an effective asymmetric reducing agent. Especially noteworthy is the fact that it can reduce aliphatic ketones such as 2-octanone or 2-butanone in efficiencies approaching 80% enantiomeric excess. Several analogues have been tested in order to probe the structural features which contribute to making this reagent effective. The ether group evidently plays a role in obtaining high selectivity, since changing oxygen to nitrogen or sulfur causes a drop in selectivity. Moving the ether group by one atom in either direction or making it more hindered causes a drop in selectivity. However, replacing the OCH2C6H5 group with a methyl group also results in an effective reducing agent and suggests that steric factors play an important role. The lithium cation was also found to be very important. Whereas the lithium compound reduced acetophenone within minutes at -78-degrees-C, the potassium analogue gave no reduction over an extended period. At higher temperatures (-65-degrees-C) reduction did slowly occur with the potassium compound, but the selectivity was greatly reduced in comparison to the lithium compound.