1-[(1S)-ketopinyl]piperidine | 136088-00-1

• 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: 1-[(1S)-ketopinyl]piperidine
• 英文别名: 7,7-dimethyl-1-(piperidine-1-carbonyl)bicyclo[2.2.1]heptane-2-one；(1S,4R)-7,7-dimethyl-1-(piperidine-1-carbonyl)bicyclo[2.2.1]heptan-2-one
• CAS: 136088-00-1
• 化学式: C₁₅H₂₃NO₂
• 分子量: 249.353
• InChiKey: PTKFPUSMAFDTLO-ABAIWWIYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.39
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  37.38
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-[(1S)-ketopinyl]piperidine 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 生成 ((1S,2R,4R)-2-hydroxy-7,7-dimethylbicyclo[2.2.1]heptan-1-yl)(piperidin-1-yl)methanone
  参考文献：
  名称：

  Highly diastereoselective synthesis of pyrido[2,1-b][1,3]oxazin-4(6H)-one by intramolecular anodic oxidation

  摘要：

  This paper describes a method for the intramolecular anodic oxidation of omega-hydroxyl amides. Products were obtained in acceptable yields from different starting materials using various applied currents, charge, and reactant concentrations. Compounds 1a and 1d afforded a single diastereomer in 67% yield when the applied current and reactant concentration were 100 mA and 0.04 M. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.08.017
• 作为产物：
  描述：

  (S)-(+)-酮基蒎酸 在 氯化亚砜 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 1-[(1S)-ketopinyl]piperidine
  参考文献：
  名称：

  Enantioselective Addition of Diethylzinc to Aldehydes Catalyzed by (1R,2R)-10-(Dialkylamino)isoborneols

  摘要：

  (1R,2R)-10-二烷基氨基异冰片醇，即γ-氨基醇型配体，由(+)-酮苦杏仁酸合成。其作为手性配体对二乙基锌对醛的不对称加成反应的催化能力进行了评估。其中，以9-氮杂双环[3.3.1]壬烷-9-基团作为氨基部分的配体最为有效，并对多种醛表现出良好的对映选择性。

  DOI：

  10.1055/s-2005-861788

文献信息

• Enantioselective addition of organozinc reagents to carbonyl compounds catalyzed by a camphor derived chiral γ-amino thiol ligand
  作者：Hsyueh-Liang Wu、Ping-Yu Wu、Ying-Ni Cheng、Biing-Jiun Uang

  DOI：10.1016/j.tet.2015.07.038

  日期：2016.5

  synthesis of the chiral camphor derived γ-amino thiol ligand 17 and its application in catalytic enantioselective carbon-carbon forming reactions through the addition of organozinc reagents to carbonyl compounds is described. The catalytic activity and enantioselectivity of ligand 17 is demonstrated in the enantioselective addition of various organozinc reagents to aldehydes and ketoesters, offering the corresponding

  在本文中，描述了手性樟脑衍生的γ-氨基硫醇配体17的设计和合成，以及通过向羰基化合物中添加有机锌试剂在催化对映选择性碳-碳形成反应中的应用。配体17的催化活性和对映选择性通过将各种有机锌试剂对映选择性加成到醛和酮酯中得到证明，从而以高收率和对映选择性提供相应的醇。还讨论了巯基在有机锌与醛的高度对映选择性1,2加成反应中的作用。
• Hydroxyamide-catalyzed enantioselective addition of diethylzinc to benzaldehyde in the absence of titanium
  作者：Tomás de las Casas Engel、Beatriz Lora Maroto、Antonio García Martínez、Santiago de la Moya Cerero

  DOI：10.1016/j.tetasy.2008.02.025

  日期：2008.4

  Three camphor-based tertiary-amido isoborneols have been obtained from ketopinic acid and tested as ligands for the hydroxy-amide-catalyzed enantioselective addition of diethylzinc to benzaldehyde in the absence of Ti(O-i-Pr)(4). The results obtained have been compared with previous results published by Oppolzer. The new chiral ligands showed effective asymmetric activity in the absence of titanium (up to 98% yield and 90% ee). It is demonstrated that non-bulky dialkylamino groups are necessary for obtaining high chemical yields, whereas the C-2 symmetry is necessary to reach a good enantioselection level. (c) 2008 Elsevier Ltd. All rights reserved.