4,5-dihydro-3-nitro-4-<(tetrahydro-2H-pyran-2-yl)oxy>isoxazole | 346619-07-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: 4,5-dihydro-3-nitro-4-<(tetrahydro-2H-pyran-2-yl)oxy>isoxazole
• 英文别名: 3-Nitro-4-tetrahydro-pyran-2-yloxy-4,5-dihydro-isoxazole；3-nitro-4-(oxan-2-yloxy)-4,5-dihydro-1,2-oxazole
• CAS: 346619-07-6
• 化学式: C₈H₁₂N₂O₅
• 分子量: 216.194
• InChiKey: TUAHCTQHSMQNLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  85.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,5-dihydro-3-nitro-4-<(tetrahydro-2H-pyran-2-yl)oxy>isoxazole 在 diisobutylaluminum hydride 作用下， 以 二甲基亚砜 为溶剂， 生成 (E)-3-[4-(Tetrahydro-pyran-2-yloxy)-4,5-dihydro-isoxazol-3-yl]-propenal
  参考文献：
  名称：

  生成4-氧异恶唑啉的新途径。在合成2-脱氧-2-氨基丁糖衍生物中的应用

  摘要：

  通过连续的硝基缩醛亚硝化环化策略制备的4，5-二氢-3-硝基-4-异恶唑的THP醚被转化为4，5-二氢-3-（二硫代戊酰基）异恶唑。随后的LBH还原分别得到2-脱氧-2-氨基苏糖和-赤藓糖衍生物的95：5非对映异构体混合物，将其环化为四氢-2 H -1,3-恶嗪-2-酮的混合物。

  DOI：

  10.1016/s0040-4039(00)72711-0
• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 在 亚硝酸丙酯 、 sodium carbonate 、 sodium nitrite 作用下， 以 二甲基亚砜 为溶剂， 生成 4,5-dihydro-3-nitro-4-<(tetrahydro-2H-pyran-2-yl)oxy>isoxazole
  参考文献：
  名称：

  生成4-氧异恶唑啉的新途径。在合成2-脱氧-2-氨基丁糖衍生物中的应用

  摘要：

  通过连续的硝基缩醛亚硝化环化策略制备的4，5-二氢-3-硝基-4-异恶唑的THP醚被转化为4，5-二氢-3-（二硫代戊酰基）异恶唑。随后的LBH还原分别得到2-脱氧-2-氨基苏糖和-赤藓糖衍生物的95：5非对映异构体混合物，将其环化为四氢-2 H -1,3-恶嗪-2-酮的混合物。

  DOI：

  10.1016/s0040-4039(00)72711-0

文献信息

• 2-Amino-2-deoxytetrose Derivatives. Preparation from 4,5-Dihydroisoxazoles via Reductive Cleavage
  作者：Peter A. Wade、Stephen G. D'Ambrosio、David T. Price

  DOI：10.1021/jo00125a015

  日期：1995.10

  The 4-alkoxy-3-nitro-4,5-dihydroisoxazoles 2a,b were prepared by condensation of nitromethane and chloroacetaldehyde, protection of the resulting nitroaldol Ic, and subsequent nitrosative cyclization. Multistep replacement of the nitro group of 2a,b by a 2-(1,3-dithiolanyl) group gave 7a,b. Reaction of 7b with lithium borohydride afforded reductive cleavage of the dihydroisoxazole ring to produce the open-chain diastereomeric amino alcohols 6a,b. A reproducible ratio of > 90: 10 6a/6b was obtained using freshly prepared hydride reagent. The amino alcohols were converted to the corresponding (R*,R*)-amide 6c and (R*,S*)-amide 6d which were chromatographically separated. The(R*,R*)-amide was transformed into the 2-amino-2-deoxythreose derivatives 11a,b and hence to 12 while the (R*,S*)-amide was similarly transformed to 2-amino-2-deoxyerythrose derivative 14a and its anomeric isomer 14b.
• Chemoenzymatic synthesis of acetyl (R)-(+)- and (S)-(−)-cycloserine
  作者：Marco de Amici、Carlo de Micheli、Francesca Cateni、Giacomo Carrea、Gianluca Ottolina

  DOI：10.1016/s0957-4166(00)80156-1

  日期：1993.5

  The two enantiomers of acetyl cycloserine 8, the immediate precursors of the chiral forms of cycloserine 1, were prepared in enantiomeric excess higher than 98% by means of lipase-catalyzed hydrolysis of 3-benzyloxy-4-hydroxy-DELTA2-isoxazoline butyrate (+/-)-5. Among the five lipases tested, lipase from Chromobacterium viscosum was by far the most selective catalyst. Since the enantiomeric ratio (E) of the reaction was higher than 100, the hydrolysis spontaneously stopped at 50% conversion to yield (R)-3-benzyloxy-4-hydroxy-DELTA2-isoxazoline [(R)-(+)-4] and (S)-3-benzyloxy-4-hydroxy-DELTA2-isoxazoline butyrate [(S)-(-)-5] in almost enantiomerically pure form. Intermediates (R)-(+)-4 and (S)-(-)-5 were transformed into the enantiomers of acetyl cycloserine through a four step sequence. This strategy constitutes a valid alternative to the previously reported procedures.
• WADE, PETER A.;PRICE, DAVID T., TETRADEHRON LETT., 30,(1989) N0, C. 1185-1188
  作者：WADE, PETER A.、PRICE, DAVID T.

  DOI：——

  日期：——
• [DE] 3-NITRO-DIHYDRO-ISOXAZOLE UND -OXAZINE<br/>[EN] 3-NITRO-DIHYDRO-ISOXAZOLES AND -OXAZINES<br/>[FR] 3-NITRO-DIHYDRO-ISOXAZOLE ET -OXAZINE
  申请人：BAYER AG

  公开号：WO2001046163A2

  公开（公告）日：2001-06-28

  Die Erfindung betrifft die Verwendung teilweise bekannter Isoxazole und Oxazine der Formel (I), in welcher W für CR?1R2-CR3R4¿ oder CR?5R6-CR7R8-CR9R10¿ steht, worin R?1, R2, R3, R4, R5, R7, R8, R9 und R10¿ unabhängig voneinander stehen für Wasserstoff, Halogen, Cyano, Nitro, jeweils gegebenenfalls substituiertes Alkyl, Alkenyl oder Alkinyl, gegebenenfalls substituiertes Aryl, -OR?11, -OCOR12¿, -OCOOR13, -OCONR14R15, -OSO¿2R?16, -OSO-¿2?NR?17R18, -OC(R19)(OR20¿), wobei R?11, R12, R13, R14, R15, R16, R17, R18, R19 und R20¿ unabhängig voneinander stehen können für Wasserstoff, jeweils gegebenenfalls substituiertes Alkyl, Alkenyl, Alkinyl oder gegebenenfalls substituiertes Aryl, als Biozide.
• A new route to 4-oxygenated isoxazolines. Application to the synthesis of 2-deoxy-2-aminobutose derivatives
  作者：Peter A. Wade、David T. Price

  DOI：10.1016/s0040-4039(00)72711-0

  日期：1989.1

  The THP ether of 4,5-dihydro-3-nitro-4-isoxazolol, prepared by a sequential nitroaldol nitrosative cyclization strategy, was converted to a 4,5-dihydro-3-(dithiolanyl)isoxazole; subsequent LBH reduction gave a 95:5 diastereomeric mixture of 2-deoxy-2-aminothreose and -erythrose derivatives, respectively, which was cyclized to a mixture of tetrahydro-2H-1,3-oxazine-2-ones.

  通过连续的硝基缩醛亚硝化环化策略制备的4，5-二氢-3-硝基-4-异恶唑的THP醚被转化为4，5-二氢-3-（二硫代戊酰基）异恶唑。随后的LBH还原分别得到2-脱氧-2-氨基苏糖和-赤藓糖衍生物的95：5非对映异构体混合物，将其环化为四氢-2 H -1,3-恶嗪-2-酮的混合物。