(6S)-1-aza-2,3-didehydro-8-oxabicyclo[4.3.0]nonan-9-one | 87842-81-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (6S)-1-aza-2,3-didehydro-8-oxabicyclo[4.3.0]nonan-9-one
• 英文别名: (8aS)-1,7,8,8a-tetrahydro-[1,3]oxazolo[3,4-a]pyridin-3-one
• CAS: 87842-81-7
• 化学式: C₇H₉NO₂
• 分子量: 139.154
• InChiKey: XUHIOFZVXGYEAK-LURJTMIESA-N

物化性质

• 沸点：
  199.9±23.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 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：

  (6S)-1-aza-2,3-didehydro-8-oxabicyclo[4.3.0]nonan-9-one 生成 (R)-2-哌啶甲醇
  参考文献：
  名称：

  旋光性β-巯基羧酸酯的新合成

  摘要：

  光学活性的β-巯基羧酸酯的合成已经通过一种新的方法来实现，该方法利用光学活性的N-甲氧基羰基哌啶衍生物作为模板，可以由L-赖氨酸通过阳极氧化制备。

  DOI：

  10.1016/s0040-4039(00)93586-x
• 作为产物：
  描述：

  (S)-3,4-二氢-2H-吡啶-1,2-二羧酸二甲酯 在 sodium tetrahydroborate 作用下， 以 甲醇 、 乙二醇二甲醚 为溶剂， 以80%的产率得到(6S)-1-aza-2,3-didehydro-8-oxabicyclo[4.3.0]nonan-9-one
  参考文献：
  名称：

  旋光性β-巯基羧酸酯的新合成

  摘要：

  光学活性的β-巯基羧酸酯的合成已经通过一种新的方法来实现，该方法利用光学活性的N-甲氧基羰基哌啶衍生物作为模板，可以由L-赖氨酸通过阳极氧化制备。

  DOI：

  10.1016/s0040-4039(00)93586-x

文献信息

• First synthesis of optically pure α-amino amine as asymmetric amino transfer reagent and its use in asymmetric Mannich reaction
  作者：Yoshishiro Matsumura、Takashi Tomita

  DOI：10.1016/s0040-4039(00)73085-1

  日期：1994.5

  An optically pure α-amino amine was first synthesized from L-lysine utilizing anodic oxidation as a key step, and its usefulness was exemplified by the asymmetric Mannich reaction to give optically active β-amino acid esters.

  首先，以阳极氧化为关键步骤，由L-赖氨酸合成光学纯的α-氨基胺，其有用性通过不对称曼尼希反应来举例说明，可以得到光学活性的β-氨基酸酯。
• Stereoselective synthesis of azasugars by electrochemical oxidation
  作者：Shigeru Furukubo、Noriaki Moriyama、Osamu Onomura、Yoshihiro Matsumura

  DOI：10.1016/j.tetlet.2004.09.036

  日期：2004.10

  A new method using electrochemical oxidation has been exploited for the stereoselective synthesis of 2,3,6-trihydroxylated 5S-piperidine derivatives. The electrochemical method was Successively used for the conversion of N-protected piperidines to N-protected 1-methoxypiperidines and for the conversion of 1-methoxy-2,3-didehydropiperidine derivatives to 1,2,3-triacetoxypiperidine derivatives. The method provided a new synthetic route to 2S,3S,6-triacetoxy-5S-methylpiperidine and 2R,3R,6-triacetoxy-5S-methylpiperidine. (C) 2004 Elsevier Ltd. All rights reserved.
• Stereoselective synthesis of 3-deoxy-piperidine iminosugars from l-lysine
  作者：Noriaki Moriyama、Yoshihiro Matsumura、Masami Kuriyama、Osamu Onomura

  DOI：10.1016/j.tetasy.2009.11.028

  日期：2009.12

  A new method using electrochemical oxidation and/or OsO4 oxidation has been used for the stereoselective synthesis of 2,3,6-trihydroxylated (5S)-piperidine derivatives. The electrochemical method was successively used for the conversion of N-protected piperidines to N-protected 1-methoxpiperidines and for the conversion of 2,3-didehydro-1-methoxypiperidine derivatives to 2,3-trans-1,2,3-triacetoxypiperidine derivatives. These triacetates were easily transformed into (2S,3S)-6-triacetoxy-(5S)-methylpiperidine and (2R,3R)-6-triacetoxy-(5S)-methylpiperidine. In addition, the 2,3-cis-dihydroxylation of 2,3-didehydro-1-methoxypiperidine derivatives with OsO4 afforded (2R,3S)-6-triacetoxy-(5S)-methylpiperidine and (2S,3R)-(3-triacetoxy-(5S)-methylpiperidine. (C) 2009 Elsevier Ltd. All rights reserved.
• Diastereoselective Cyclopropanation Utilizing a New Chiral<i>N,O</i>-Acetals Prepared by Electrochemical Oxidation of Carbamates
  作者：Yoshihiro Matsumura、Tsuyoshi Asano、Takeshi Nakagiri、Osamu Onomura

  DOI：10.1002/jccs.199800047

  日期：1998.4

  AbstractA new chiral bicyclic tetrahydropyridine derivative was synthesized from L‐lysine derivatives utilizing electrochemical oxidation as a key step. Allyl alcohols were incorporated into the tetrahydropyridine derivative to afford N,O‐acetals, and the reaction of the resulting N,O‐acetals with a carbenoid, which was generated from Et2Zn and CH2l2, yielded cyclopropanated products in moderate diastereoselectivities.