3-methyl-4,5-dihydroisoxazole-5-carboxylic acid ethyl ester | 87823-46-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 3-methyl-4,5-dihydroisoxazole-5-carboxylic acid ethyl ester
• 英文别名: (+/-)-ethyl 3-methyl-4,5-dihydroisoxazole-5-carboxylate；ethyl 3-methyl-4,5-dihydroisoxazole-5-carboxylate；ethyl 3-methyl-4,5-dihydro-1,2-oxazole-5-carboxylate
• CAS: 87823-46-9
• 化学式: C₇H₁₁NO₃
• 分子量: 157.169
• InChiKey: PANVQYQDKCEJEG-UHFFFAOYSA-N

物化性质

• 沸点：
  95-110 °C(Press: 10 Torr)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-methyl-4,5-dihydroisoxazole-5-carboxylic acid ethyl ester 在 molybdenum hexacarbonyl 、 一水合肼 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 2.0h， 生成 5-Hydroxy-3-methyl-4,5-dihydro-pyridazon-(6)
  参考文献：
  名称：

  Nitrile Oxide [3 + 2] Cycloaddition: Application to the Synthesis of 6-Substituted 3(2H)-Pyridazinones and 6-Substituted 4,5-Dihydro-4-hydroxy-3(2H)-pyridazinones

  摘要：

  描述了一种从3,5-二取代的4,5-二氢异噁唑出发，高效制备6-取代的3(2H)-吡嗪酮和6-取代的4,5-二氢-4-羟基-3(2H)-吡嗪酮的方法。通过六羰基钼或催化氢化促进异噁唑啉环的N-O键断裂，获得了α-羟基γ-酮酯4a-f，这些酯在室温或回流条件下与水合肼反应生成6-取代的4,5-二氢-4-羟基-3(2H)-吡嗪酮5a-f或6-取代的3(2H)-吡嗪酮6a-f，且收率较高。该协议的灵活性通过从已知的β-核糖硝基甲烷8合成C-核糖苷7得到了验证。此外，还开发了一种分子内版本的方法来制备已知的抗溃疡三环3(2H)-吡嗪酮12。

  DOI：

  10.1055/s-1994-25663
• 作为产物：
  描述：

  异氰酸苯酯 以73%的产率得到
  参考文献：
  名称：

  Yang S., Hayden W., Griengl H., Monatsh. Chem, 125 (1994) N 4, S 469-477

  摘要：

  DOI：

文献信息

• An Improved Method for Preparation of Nitrile Oxides from Nitroalkanes for In Situ Dipolar Cycloadditions
  作者：Yochai Basel、Alfred Hassner

  DOI：10.1055/s-1997-1181

  日期：1997.3

  A new method has been found for generation of nitrile oxides in situ from nitroalkanes under mild conditions. Thus, reaction of nitroalkanes 1 with di-tert-butyl dicarbonate (2) and 4-dimethyl-aminopyridine (3) as catalyst in the presence of dipolarophiles at room temperature afforded cycloadducts (e.g. 5,6, and 7) in improved yields compared to known methods. Solvent effects were also noted.

  已发现一种新方法，可以在温和条件下从硝基烷烃原位生成腈氧化物。因此，将硝基烷烃1与二叔丁基二羧酸酯（2）和含有催化剂的4-二甲基氨基吡啶（3）在室温下与极性偶极体反应，得到了环加成产物（例如5、6和7），其产率相比已知方法有了改善。同时也观察到了溶剂效应。
• A method for generating nitrile oxides from nitroalkanes: a microwave assisted route for isoxazoles
  作者：Giampaolo Giacomelli、Lidia De Luca、Andrea Porcheddu

  DOI：10.1016/s0040-4020(03)00859-7

  日期：2003.7

  A convenient route has been developed for generation of nitrile oxides in situ from nitroalkanes under very mild conditions using microwave irradiation, using 4-(4,6-dimethoxy[1,3,5]triazin-2-yl)-4-methylmorpholinium chloride (DMTMM) and DMAP as catalyst. Isoxazolines and isoxazoles are obtained in very good yields compared to known methods.

  已经开发了一种简便的方法，可以使用4-（4,6-二甲氧基[1,3,5]三嗪-2-基）-4-甲基吗啉鎓盐在非常温和的条件下使用微波辐射从硝基烷烃原位生成腈氧化物（DMTMM）和DMAP作为催化剂。与已知方法相比，以非常好的产率获得了异恶唑啉和异恶唑。
• Safe and Convenient Reduction of Δ²-Isoxazolines with PMHS-Pd(OH)₂/C
  作者：S. Chandrasekhar、B. Nagendra Babu、Moinuddin Ahmed、M. Venkat Reddy、P. Srihari、B. Jagadeesh、A. Prabhakar

  DOI：10.1055/s-2004-822917

  日期：——

  A practical and safe reduction methodology for the conversion of Δ2-isoxazolines to 1,3-aminols is developed using polymethylhydrosiloxane-Pd(OH)2/C. In presence of (Boc)2O, the isoxazoline was converted into N-Boc protected 1,3-aminol in a one-pot procedure.

  利用聚甲基氢硅氧烷-Pd(OH)2/C，开发了一种实用安全的将δ2-异噁唑啉转化为 1,3-氨基醇的还原方法。在 (Boc)2O 的存在下，异噁唑啉通过一锅程序转化为 N-Boc 保护的 1,3-氨基醇。
• Resolution of ?2-isoxazoline-5-carboxylates by a protease fromAspergillus Oryzae providing masked synthons for enantiopure ?-aminoalcohols and related structures
  作者：S. Yang、W. Hayden、H. Griengl

  DOI：10.1007/bf00811865

  日期：1994.4

  A series of racemic DELTA2-isoxazolinecarboxylates have been synthesized and subjected to enzymatic hydrolysis by a protease from Aspergillus oryzae in a two-phase system. Out of these compounds only isoxazoline-5-carboxylates unsubstituted at C-4 were hydrolyzed. Thus, from 3-ethoxycarbonyl-, 3-methyl-, and 3-phenyl-DELTA2-isoxazoline-5-carboxylates the corresponding (R)-configurated carboxylic acids are obtained. In contrast, an additional methyl group at C-5 changes the steric course of the hydrolysis to give predominantly the (S)-acid. The enantioselectivities obtained are in the range of E = 5-35.
• FURUKAWA, ISAO;NISHIOKA, YOSHIHIRO;HASHIMOTO, SHIZUNOBU, SCI. AND ENG. REV. DOCHISHA UNIV., 1983, 24, N 1, 69-77
  作者：FURUKAWA, ISAO、NISHIOKA, YOSHIHIRO、HASHIMOTO, SHIZUNOBU

  DOI：——

  日期：——