(S)-1,5,6,8a-tetrahydro-3H-oxazolo[3,4-a]pyridin-3-one | 332188-53-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (S)-1,5,6,8a-tetrahydro-3H-oxazolo[3,4-a]pyridin-3-one
• 英文别名: (8aS)-1,5,6,8a-tetrahydro-[1,3]oxazolo[3,4-a]pyridin-3-one
• CAS: 332188-53-1
• 化学式: C₇H₉NO₂
• 分子量: 139.154
• InChiKey: HQACCHHRMWGEPO-LURJTMIESA-N

物化性质

• 沸点：
  330.4±32.0 °C(predicted)
• 密度：
  1.25±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-1,5,6,8a-tetrahydro-3H-oxazolo[3,4-a]pyridin-3-one 在 甲醇 、 potassium cyanide 、 sodium hydroxide 、 碘 、 镍 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 24.0h， 生成 ((2S,4S)-4-Methoxymethoxy-piperidin-2-yl)-methanol
  参考文献：
  名称：

  Synthesis of (2 R ,4 R )- and (2 S ,4 S )-4-hydroxypipecolic acid derivatives and (2 S ,4 S )-(−)-SS20846A

  摘要：

  Syntheses of protected derivatives of both enantiomers of trans-4-hydroxypipecolic acid (2) and the natural product (-)-SS20846A (3) were accomplished from vinylglycinols. Key transformations involved construction of the piperidine ring via ring-closing metathesis (Grubbs' catalyst) and installation of the 4-hydroxy substituent by Prevost reaction. X-Ray diffraction analyses conclusively established the regio- and stereochemistry of key intermediates. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02124-9
• 作为产物：
  描述：

  (S)-3-But-3-enyl-4-vinyl-oxazolidin-2-one 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以88%的产率得到(S)-1,5,6,8a-tetrahydro-3H-oxazolo[3,4-a]pyridin-3-one
  参考文献：
  名称：

  Synthesis of (2 R ,4 R )- and (2 S ,4 S )-4-hydroxypipecolic acid derivatives and (2 S ,4 S )-(−)-SS20846A

  摘要：

  Syntheses of protected derivatives of both enantiomers of trans-4-hydroxypipecolic acid (2) and the natural product (-)-SS20846A (3) were accomplished from vinylglycinols. Key transformations involved construction of the piperidine ring via ring-closing metathesis (Grubbs' catalyst) and installation of the 4-hydroxy substituent by Prevost reaction. X-Ray diffraction analyses conclusively established the regio- and stereochemistry of key intermediates. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02124-9

文献信息

• Sn−Li Transmetalation of α‐Aminoorganostannanes for the Stereoselective Synthesis of Substituted Dehydropiperidines and Dehydroazepanes
  作者：Alexandre Lumbroso、Isabelle Beaudet、Jean‐Paul Quintard、Cécile Fraisse、Nicolas Galland、Loïc Toupet、Erwan Le Grognec

  DOI：10.1002/adsc.201900349

  日期：2019.8.21

  A highly diastereoselective synthesis of (R,S) or (S,S) 2,6‐disubstituted dehydropiperidines and 2,7‐disubstituted dehydroazepanes has been developed. The stereochemical preference for the (R,S) or the (S,S) isomer is governed by a tin‐lithium exchange/electrophilic trapping sequence combined with a ring‐closing metathesis. Their relative order was found to have a dramatic influence on the interaction

  已开发出（R，S）或（S，S）2,6-二取代的脱氢哌啶和2,7-二取代的脱氢氮杂环庚烷的高度非对映选择性合成。（R，S）或（S，S）异构体的立体化学偏好是由锡-锂交换/亲电子捕获序列与闭环复分解相结合决定的。发现它们的相对顺序对控制阴离子中心差向异构的相互作用有很大的影响。在每种情况下，反应序列的完全立体发散都是通过考虑羰基锂配位带来的稳定性并通过DFT计算合理化来解释的。
• Concise stereoselective synthesis of cis-3-alkoxy-2-carbomethoxy medium-ring oxacycles from (R)-3-(3-butenyl)-4-propynoyloxazolidin-2-one
  作者：Daisuke Sato、Kenshu Fujiwara、Hidetoshi Kawai、Takanori Suzuki

  DOI：10.1016/j.tetlet.2007.12.111

  日期：2008.2

  A concise process for the stereoselective synthesis of chiral cis-3-alkoxy-2-carbomethoxy medium-ring oxacycles from (R)-3-(3-butenyl)-4-propynoyloxazolidin-2-one (1) was developed. The process includes five major steps: (i) hetero-Michael reaction between an alcohol and 1, (ii) stereoselective reduction of the resulting ketone, featuring stereochemical assistance of the neighboring oxazolidin-2-one

  开发了一种简明的方法，用于从（R）-3-（3-丁烯基）-4-丙炔基恶唑烷丁二酮（1）立体选择性地合成手性顺式-3-烷氧基-2-羰甲氧基中环氧杂环。该方法包括五个主要步骤：（i）醇与1之间的杂-迈克尔反应，（ii）立体选择性还原生成的酮，其特征在于相邻的恶唑烷二-2-酮基团的立体化学辅助，（iii）用烷氧基酯化乙酸，（iv）生成的手性转移的爱尔兰–克莱森重排，生成3-烷氧基烯丙基乙醇酸酯，以提供顺式-2，3-二烷氧基羧酸酯，和（v）中继闭环烯烃复分解反应以形成中环醚，同时除去恶唑烷-2-酮部分。