2-(S)-(methoxycarbonylmethyl)-6-(S)-methylpiperidine | 163956-51-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 2-(S)-(methoxycarbonylmethyl)-6-(S)-methylpiperidine
• 英文别名: methyl 2-[(2S,6S)-6-methylpiperidin-2-yl]acetate
• CAS: 163956-51-2
• 化学式: C₉H₁₇NO₂
• 分子量: 171.239
• InChiKey: ALWGFJCAACSPRJ-YUMQZZPRSA-N

物化性质

• 沸点：
  225.2±13.0 °C(Predicted)
• 密度：
  0.951±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(S)-(methoxycarbonylmethyl)-6-(S)-methylpiperidine 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 苯甲醚 、 三苯基膦 、 三氟乙酸 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 7-chloro-3-(3,5-dimethylphenyl)-4-[2-[(2S,6S)-6-methylpiperidin-2-yl]ethoxy]-2-oxo-N-pyrimidin-4-yl-1H-quinoline-6-carboxamide
  参考文献：
  名称：

  Syntheses and structure–activity relationship studies of piperidine-substituted quinolones as nonpeptide gonadotropin releasing hormone antagonists

  摘要：

  Syntheses and structure-activity relationships of piperidine-substituted quinolones as nonpeptide gonadotropin releasing hormone antagonists are described. Some of substituents on the piperidine ring that were investigated included a fused phenyl group, a (6R)-trifluoromethyl group, (6S) and (6R)-methyl group. This study showed that GnRH binding potency was tolerated by a small group at the 6-position of the piperidine, and blocking the 6-position by a trifluoromethyl group reduced clearance rate and increased oral bioavailability. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.12.101
• 作为产物：
  描述：

  (3S,8aR)-8a-methyl-3-phenyl-3,6,7,8-tetrahydro-2H-[1,3]oxazolo[3,2-a]pyridine-5-thione 在 palladium dihydroxide 氢气 、 三乙胺 、 三甲氧基磷 作用下， 反应 12.0h， 生成 2-(S)-(methoxycarbonylmethyl)-6-(S)-methylpiperidine
  参考文献：
  名称：

  A Novel Asymmetric Route to Chiral, Nonracemic cis-2,6-Disubstituted Piperidines. Synthesis of (+)-Pinidinone and (+)-Monomorine

  摘要：

  DOI：

  10.1021/ja00124a039

文献信息

• Stereocontrolled reduction of chiral pyrrolidine and piperidine β-enamino esters: formal enantioselective synthesis of (+)-calvine
  作者：Sandrine Calvet-Vitale、Corinne Vanucci-Bacqué、Marie-Claude Fargeau-Bellassoued、Gérard Lhommet

  DOI：10.1016/j.tet.2005.05.079

  日期：2005.8

  The results of a study dealing with the chemio- and diastereoselective reduction of chiral pyrrolidine and piperidine β-enamino esters 1, 2 and 3, 4 into β-amino esters are reported. This approach was successfully applied to a formal synthesis of (+)-calvine.

  一个研究交易与chemio-和非对映选择性还原的手性吡咯烷和哌啶β烯氨基酯的结果1，2和3，4为β氨基酯的报道。此方法已成功应用于（+）-牛磺酸的正式合成。
• Total Synthesis of the Galbulimima Alkaloid (−)-GB17
  作者：Reed T. Larson、Michael D. Clift、Regan J. Thomson

  DOI：10.1002/anie.201108227

  日期：2012.3.5

  A tale of two Michaels: The first enantioselective total synthesis of (−)‐GB17 is reported. Construction of this unique naphthoquinolizinone skeleton was achieved by two stereoselective intramolecular Michael additions, one under catalyst control and the other under substrate control.

  两个迈克尔的故事：报道了 (-)-GB17 的第一个对映选择性全合成。这种独特的萘并喹啉酮骨架的构建是通过两种立体选择性分子内迈克尔加成实现的，一种在催化剂控制下，另一个在底物控制下。
• Syntheses and structure–activity relationship studies of piperidine-substituted quinolones as nonpeptide gonadotropin releasing hormone antagonists
  作者：Jinlong Jiang、Robert J. DeVita、Mark T. Goulet、Matthew J. Wyvratt、Jane-L. Lo、Ning Ren、Joel B. Yudkovitz、Jisong Cui、Yi T. Yang、Kang Cheng、Susan P. Rohrer

  DOI：10.1016/j.bmcl.2003.12.101

  日期：2004.4

  Syntheses and structure-activity relationships of piperidine-substituted quinolones as nonpeptide gonadotropin releasing hormone antagonists are described. Some of substituents on the piperidine ring that were investigated included a fused phenyl group, a (6R)-trifluoromethyl group, (6S) and (6R)-methyl group. This study showed that GnRH binding potency was tolerated by a small group at the 6-position of the piperidine, and blocking the 6-position by a trifluoromethyl group reduced clearance rate and increased oral bioavailability. (C) 2004 Elsevier Ltd. All rights reserved.
• A Novel Asymmetric Route to Chiral, Nonracemic cis-2,6-Disubstituted Piperidines. Synthesis of (+)-Pinidinone and (+)-Monomorine
  作者：Michael J. Munchhof、A. I. Meyers

  DOI：10.1021/ja00124a039

  日期：1995.5