(5RS)-5-<(1RS)-1-hydroxypropyl>-3-(p-methoxyphenyl)-2-isoxazoline | 138622-11-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (5RS)-5-<(1RS)-1-hydroxypropyl>-3-(p-methoxyphenyl)-2-isoxazoline
• 英文别名: (1R)-1-[(5R)-3-(4-methoxyphenyl)-4,5-dihydro-1,2-oxazol-5-yl]propan-1-ol
• CAS: 138622-11-4；138622-12-5
• 化学式: C₁₃H₁₇NO₃
• 分子量: 235.283
• InChiKey: YGZNDGANCXAWKC-CHWSQXEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  51
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-戊烯-3-醇 、 ALPHA-氯-4-甲氧基苯甲醛肟 在 乙基溴化镁 作用下， 生成 (5RS)-5-<(1RS)-1-hydroxypropyl>-3-(p-methoxyphenyl)-2-isoxazoline
  参考文献：
  名称：

  First Successful Metal Coordination Control in 1,3-Dipolar Cycloadditions. High-Rate Acceleration and Regio- and Stereocontrol of Nitrile Oxide Cycloadditions to the Magnesium Alkoxides of Allylic and Homoallylic Alcohols

  摘要：

  The first successful control of stereo- and regioselectivity in 1,3-dipolar cycloadditions by metal coordination is described. The presence of magnesium ions dramatically accelerates nitrile oxide dipolar cycloadditions to allylic alcohols, improving both the regio- and stereoselectivity of the reaction. For example, cycloadditions to terminal allylic alcohols bearing alpha-chirality produce syn-stereoisomers of 2-isoxazolines selectively, and reactions involving the magnesium alkoxides of internal allylic alcohols are exclusively regioselective in favor of 5-hydroxymethyl-2-isoxazolines. Metal alkoxides other than magnesium, such as lithium, zinc, and aluminum alkoxides, are less effective. These reactions involve the formation of activated intermediates in which a nitrile oxide and an allylic alkoxide coordinate to the magnesium ion. Theoretical calculations indicate that the formation of the coordinated intermediates enhances the rate of cycloaddition and also improves the syn-selectivity.

  DOI：

  10.1021/ja00085a012

文献信息

• Generation of nitrile oxides through O-metalation of hydroximoyl chlorides. Chelation-controlled syn-selective cycloaddition of nitrile oxides to α-substituted allyl alcohols
  作者：Shuji Kanemasa、Shigeru Kobayashi、Shigeru Kobayashi、Masaki Nishiuchi、Hidetoshi Yamamoto、Eiji Wada

  DOI：10.1016/0040-4039(91)80171-2

  日期：1991.10

  New generation of nitrile oxides by treatment of hydroximoyl chlorides with organometallics is reported. Their cycloadditions to the allyl alcohols bearing a chiral center at the 1-position proceed in a syn-selective manner, providing the first example of stereocontrol of 1,3-dipolar cycloaddition by the aid of metal chelation.

  据报道，通过用有机金属化合物处理羟肟基氯，新一代的腈氧化物。它们在1-位手性中心的烯丙醇上的环加成是以顺选择性方式进行的，这是借助金属螯合来立体控制1,3-偶极环加成的第一个例子。
• First Successful Metal Coordination Control in 1,3-Dipolar Cycloadditions. High-Rate Acceleration and Regio- and Stereocontrol of Nitrile Oxide Cycloadditions to the Magnesium Alkoxides of Allylic and Homoallylic Alcohols
  作者：Shuji Kanemasa、Masaki Nishiuchi、Akio Kamimura、Kenzi Hori

  DOI：10.1021/ja00085a012

  日期：1994.3

  The first successful control of stereo- and regioselectivity in 1,3-dipolar cycloadditions by metal coordination is described. The presence of magnesium ions dramatically accelerates nitrile oxide dipolar cycloadditions to allylic alcohols, improving both the regio- and stereoselectivity of the reaction. For example, cycloadditions to terminal allylic alcohols bearing alpha-chirality produce syn-stereoisomers of 2-isoxazolines selectively, and reactions involving the magnesium alkoxides of internal allylic alcohols are exclusively regioselective in favor of 5-hydroxymethyl-2-isoxazolines. Metal alkoxides other than magnesium, such as lithium, zinc, and aluminum alkoxides, are less effective. These reactions involve the formation of activated intermediates in which a nitrile oxide and an allylic alkoxide coordinate to the magnesium ion. Theoretical calculations indicate that the formation of the coordinated intermediates enhances the rate of cycloaddition and also improves the syn-selectivity.