<(1R, 2R)-2-methoxy-7,7-dimethylbicyclo<2.2.1>heptane-1-carbonyl>-2-oxazolone | 125554-25-8

• 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: <(1R, 2R)-2-methoxy-7,7-dimethylbicyclo<2.2.1>heptane-1-carbonyl>-2-oxazolone
• 英文别名: (-)-3-(2-Methoxy-1-apocamphanecarbonyl)-2-oxazolone；3-<(1S)-2-exo-methoxy-1-apocamphanecarbonyl>-2-oxazolone；3-[(1S,2R,4R)-2-methoxy-7,7-dimethylbicyclo[2.2.1]heptane-1-carbonyl]-1,3-oxazol-2-one
• CAS: 125554-25-8
• 化学式: C₁₄H₁₉NO₄
• 分子量: 265.309
• InChiKey: SJZDIILGJDPQAD-RULNRJAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  <(1R, 2R)-2-methoxy-7,7-dimethylbicyclo<2.2.1>heptane-1-carbonyl>-2-oxazolone 以 乙醚 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 (4R,5R)-5-allyl-3-<(1S)-2-exo-methoxy-1-apocamphanecarbonyl>-4-methoxy-2-oxazolidinone
  参考文献：
  名称：

  用于2-氨基醇的手性合成子。生物学上感兴趣的旋光性氨基羟基酸的简便制备。

  摘要：

  通过简单杂环2-恶唑酮的烯烃部分的对映选择性官能化，涉及立体定义的易替换基团的引入，然后逐步取代，为手性2-氨基醇的通用合成提供了一种有前途的方法。这种方法的多功能性在不寻常的羟基氨基酸（例如他汀和羟基谷氨酸）的手性合成中得到了证明，它们是生物活性肽的关键成分。

  DOI：

  10.1016/s0040-4020(01)80540-8
• 作为产物：
  描述：

  methyl (1S, 2R)-2-hydroxy-7,7-dimethylbicyclo<2.2.1>heptane-1-carboxylate 在 氢氧化钾 、 正丁基锂 、 水 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 8.5h， 生成 <(1R, 2R)-2-methoxy-7,7-dimethylbicyclo<2.2.1>heptane-1-carbonyl>-2-oxazolone
  参考文献：
  名称：

  Chiral electrophilic “glycinal” equivalents. New synthons for optically active α-amino acids and 4-substituted 2-oxazolidinones

  摘要：

  The thermal reaction of 3-[(IS)-2-alkoxy-1-apocamphanecarbonyl]-2-oxazolones (21a-c) with dialkyl azodicarboxylates (9) results in exclusive formation of [4 + 2] type cycloadducts (22 and 23) with moderate levels of diastereofacial selection (up to 72% d.e.). The diastereomers thus obtained were readily purified and subsequent treatment with acidic methanol followed by removal of the auxiliary with LiBH4/MeOH (1:2) gave optically pure 4-methoxy-5-hydrazino-2-oxazolidinones (26 and 27), which serve as alpha-aminoaldehyde templates useful for the synthesis of a wide variety of optically active alpha-amino acids as well as 4-alkyl and 4-aryl-2-oxazolidinones. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(96)01077-0

文献信息

• Versatile routes to chiral 4-substituted 2-oxazolidinones and .ALPHA.-amino acids. Use of chiron, (4+2) cycloadducts of dialkyl azodicarboxylates and 2-oxazolones.
  作者：Hirofumi MATSUNAGA、Tadao ISHIZUKA、Nobuhiro MARUBAYASHI、Takehisa KUNIEDA

  DOI：10.1248/cpb.40.1077

  日期：——

  The thermal reaction of 3-[(1S)-2-alkoxyl-1-apocamphanecarbonyl]-2-oxazolones with dialkyl azodicarboxylates results in exclusive formation of [4+2] type cycloadducts with moderate levels of diastereofacial selection, which serve as versatile chiral synthons for a wide variety of 4-alkyl and 4-aryl-2-oxazolidinones as well as α-amino acids.

  3-[(1S)-2-烷氧基-1-阿波伞烷酮]-2-噁唑酮与二烷基偶氮二甲酸酯的热反应导致专一性形成[4+2]型环加成物，具有中等程度的非对映面选择性，这些产物作为多功能的手性合成前体，可用于合成多种4-烷基和4-芳基-2-噁唑啉酮以及α-氨基酸。
• Extremely powerful chiral auxiliaries: Enantiomeric [4+2] cycloadducts of 2-oxazolone and 9,10-dimethylanthracene
  作者：Koreichi Kimura、Kazutaka Murata、Keiko Otsuka、Tadao Ishizuka、Mamoru Haratake、Takehisa Kunieda

  DOI：10.1016/s0040-4039(00)60110-7

  日期：1992.7

  Enantiomeric [4+2] cycloadduct-based 2-oxazolidinones (3a and4a), newly derived from 9,10-dimethylanthracene and 2-oxazolone, serve as the most effective Evans' auxiliaries so far developed in diastereoselective alkylations and Diels-Alder reactions.

  对映体[4 + 2]基于环加合物的2-恶唑烷酮（3a和4a），是新衍生自9,10-二甲基蒽和2-恶唑酮的化合物，是迄今为止在非对映选择性烷基化和Diels-Alder反应中开发的最有效的Evans助剂。 。
• New camphor-derived auxiliaries in methoxyselenylation and methoxybromination with opposite diastereofacial selectivity
  作者：Tadao Ishizuka、Seigo Ishibuchi、Takehisa Kunieda

  DOI：10.1016/s0040-4039(00)99269-4

  日期：1989.1

  Methoxyselenylation and methoxybromination of chiral 3-acyl-2-oxazolones with PhSeCl/MeOH and Br2/MeC(OMe)3 smoothly proceed to result in highly stereoselective formation of chiral synthons for β-amino alcohols, but with opposite π-facial selectivity.

  用PhSeCl / MeOH和Br 2 / MeC（OMe）3进行手性3-酰基-2-恶唑酮的甲氧基硒基化和甲氧基溴化反应平稳进行，导致β-氨基醇的手性合成子高度立体选择性形成，但π面选择性相反。
• Ishizuka, Tadao; Matsunaga, Hirofumi; Iwashita, Junji, Heterocycles, 1994, vol. 37, # 2, p. 715 - 718
  作者：Ishizuka, Tadao、Matsunaga, Hirofumi、Iwashita, Junji、Arai, Takenori、Kunieda, Takehisa

  DOI：——

  日期：——
• Conformationally rigid chiral [4+2]cycloadduct-based 2-oxazolidinones as new auxiliaries
  作者：Hirofumi Matsunaga、Koreichi Kimura、Tadao Ishizuka、Mamoru Karatake、Takehisa Kunieda

  DOI：10.1016/0040-4039(91)80573-o

  日期：1991.12

  Newly introduced enantiomerically pure [4 + 2]cycloadduct-based 2-oxazolidinones which are conformationally fixed by bicyclo[2.2.2] and [2.2.1] ring systems, serve well as exellent chiral auxiliaries in the Evans' asymmetric strategy.