(1S)-ketopinic acid

• 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: (1S)-ketopinic acid
• 英文别名: ketopinic acid；(1S)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptane-1-carboxylic acid
• 化学式: C₁₀H₁₄O₃
• 分子量: 182.219
• InChiKey: WDODWBQJVMBHCO-TYICEKJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S)-ketopinic acid 在 4-二甲氨基吡啶 、 氯化亚砜 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 butyl (1S)-ketopinate
  参考文献：
  名称：

  Stereoselective preparation of (1S, 2R)- and (1S, 2S)-2-hydroxy-7,7-dimethylbicyclo(2.2.1)heptane-1-carboxylic acids.

  摘要：

  从 (1S)-ketopinic acid（7, 7-二甲基-2-氧代双环[2.2.1]庚烷-1-羧酸）开始，轻松高产地合成了非对映纯的 (1S, 2R)- 和 (1S, 2S)-2-hydroxy-7, 7-dimethylbicyclo[2.2.1]heptane-1-carboxylic acids。后者（2-内向异构体）的关键步骤涉及碱催化(1S, 2R)-2-羟基异构体（2-外向异构体）的外延化。

  DOI：

  10.1248/cpb.38.1717

文献信息

• ORGANOCATALYST
  申请人：Chen Kwunmin

  公开号：US20110040104A1

  公开（公告）日：2011-02-17

  The present invention provides an organocatalyst of formula (I), wherein R 1 is —H, —OH, —O—Si(R 4 )(R 5 )(R 6 ) or C 1-6 alkoxy, in which R 4 , R 5 and R 6 are identical or different and independently selected from the group consisting of C 1-6 alkyl, phenyl and phenyl substituted with C 1-6 alkyl; R 2 is —OH or ═O; X 1 is one selected from the group consisting of —NH—, —S— and X 2 is one selected from the group consisting of —C(═O)—, —CH 2 — and and X 1 is different from X 2 . The high yield and enantioselectivity of an addition reaction are obtained by using the organocatalyst of the present invention.

  本发明提供了一种式(I)的有机催化剂，其中R1为—H，—OH，—O—Si(R4)(R5)(R6)或C1-6烷氧基，其中R4、R5和R6相同或不同，并且独立地选自由C1-6烷基、苯基和苯基上取代的C1-6烷基的群；R2为—OH或═O；X1为从—NH—、—S—中选择的一种；X2为从—C(═O)—、—CH2—中选择的一种；X1与X2不同。通过使用本发明的有机催化剂，可以获得加成反应的高产率和对映选择性。
• Synthesis of Nitrone‐derived Pyrrolidine Scaffolds and Their Combinatorial Libraries to Develop Selective α‐ <scp>l</scp> ‐Rhamnosidase Inhibitors
  作者：Wei‐An Chen、Huang‐Yi Li、Ashik Sayyad、Chun‐Yen Huang、Wei‐Chieh Cheng

  DOI：10.1002/asia.202200172

  日期：2022.7.15

  efficient strategy to develop selective α-l-rhamnosidase inhibitors is described. Five functionalized pyrrolidine scaffolds were rationally designed and synthesized from cyclic nitrones. Their corresponding diverse libraries prepared by combinatorial chemistry enable us to increase the chemical space of pyrrolidine-based iminosugars and allow us to identify selective and potent α-l-rhamnosidase inhibitors

  描述了开发选择性α- l-鼠李糖苷酶抑制剂的有效策略。以环状硝酮为原料，合理设计并合成了五种功能化吡咯烷支架。通过组合化学制备的相应的多样化文库使我们能够增加基于吡咯烷的亚胺糖的化学空间，并使我们能够鉴定选择性且有效的α- l-鼠李糖苷酶抑制剂。
• QUINOLINE COMPOUNDS AND METHODS OF USE
  申请人：Gaudino John

  公开号：US20110053931A1

  公开（公告）日：2011-03-03

  Compounds of Formula (I), and stereoisomers, geometric isomers, tautomers, solvates, metabolites, salts and pharmaceutically acceptable prodrugs thereof, are useful for inhibiting receptor tyrosine kinases and for treating hyperproliferative disorders mediated thereby. Methods of using compounds of Formula (I), and stereoisomers, geometric isomers, tautomers, solvates and pharmaceutically acceptable salts thereof, for in vitro, in situ, and in vivo diagnosis, prevention or treatment of such disorders in mammalian cells, or associated pathological conditions are disclosed.

  式（I）的化合物及其立体异构体、几何异构体、互变异构体、溶剂化物、代谢物、盐和药学上可接受的前药，用于抑制受体酪氨酸激酶并治疗由此介导的过度增殖性疾病。本文揭示了使用式（I）的化合物及其立体异构体、几何异构体、互变异构体、溶剂化物和药学上可接受的盐，在哺乳动物细胞中进行体外、体内和原位诊断、预防或治疗此类疾病或相关病理条件的方法。
• WO2007/146824
  申请人：——

  公开号：——

  公开（公告）日：——
• Camphor containing organocatalysts in asymmetric aldol reaction on water
  作者：Zheng-Hao Tzeng、Hung-Yao Chen、Ching-Ting Huang、Kwunmin Chen

  DOI：10.1016/j.tetlet.2008.04.122

  日期：2008.6

  A new class of bifunctional organocatalysts were synthesized and proved to be effective in catalyzing aldol reaction on water with high to excellent diastereo- and enantioselectivities. (C) 2008 Elsevier Ltd. All rights reserved.