2-[1-(氯甲基)-2-硝基乙氧基]四氢-2H-吡喃 | 124010-16-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 中文名称: 2-[1-(氯甲基)-2-硝基乙氧基]四氢-2H-吡喃
• 英文名称: 2-<1-(chloromethyl)-2-nitroethoxy>tetrahydro-2H-pyran
• 英文别名: 2-(1-Chloro-3-nitropropan-2-yl)oxyoxane
• CAS: 124010-16-8；124010-17-9
• 化学式: C₈H₁₄ClNO₄
• 分子量: 223.656
• InChiKey: XQRRMTKSCVFTGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  64.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[1-(氯甲基)-2-硝基乙氧基]四氢-2H-吡喃 在 亚硝酸丙酯 、 sodium nitrite 作用下， 以 二甲基亚砜 为溶剂， 以71%的产率得到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
• 作为产物：
  描述：

  3,4-二氢-2H-吡喃 、 1-氯-3-硝基-丙-2-醇 在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 生成 2-[1-(氯甲基)-2-硝基乙氧基]四氢-2H-吡喃
  参考文献：
  名称：

  2-Amino-2-deoxytetrose Derivatives. Preparation from 4,5-Dihydroisoxazoles via Reductive Cleavage

  摘要：

  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.

  DOI：

  10.1021/jo00125a015

文献信息

• 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。
• 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：——
• 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.