(2'R,3S,3a'S,7'S)-1,2'-dimethyl-7'-phenyl-6',7'-dihydrospiro[indole-3,3'-isoxazolo[3,2-c][1,4]oxazine]-2,4'(1H,3a'H)-dione | 1024796-33-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2'R,3S,3a'S,7'S)-1,2'-dimethyl-7'-phenyl-6',7'-dihydrospiro[indole-3,3'-isoxazolo[3,2-c][1,4]oxazine]-2,4'(1H,3a'H)-dione
• 英文别名: (2R,3S,3aS,7S)-1',2-dimethyl-7-phenylspiro[2,3a,6,7-tetrahydro-[1,2]oxazolo[3,2-c][1,4]oxazine-3,3'-indole]-2',4-dione
• CAS: 1024796-33-5
• 化学式: C₂₁H₂₀N₂O₄
• 分子量: 364.401
• InChiKey: RPOBVTIYVSGBBZ-QFDFAYKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2'R,3S,3a'S,7'S)-1,2'-dimethyl-7'-phenyl-6',7'-dihydrospiro[indole-3,3'-isoxazolo[3,2-c][1,4]oxazine]-2,4'(1H,3a'H)-dione 在 (3E)-3-ethylidene-1-methyl-1,3-dihydro-2H-indol-2-one 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 (3E)-3-ethylidene-1-methyl-1,3-dihydro-2H-indol-2-one
  参考文献：
  名称：

  Total Synthesis of Maremycins A and D1 Using Chiral and Cyclic Nitrone with (E)-3-Ethylidene-1-methylindolin-2-one

  摘要：

  Total syntheses of maremycin A (4) and maremycin D, (8) were described, featuring 1,3-dipolar cycloaddition of a chiral cyclic nitrone 15 with (E)-3-ethylidene-1-methylindolin-2-one (13). The cycloaddition was reversible, especially at high temperature in the presence of a Lewis acid or in a solvent possessing a high acceptor number. One of the cycloadducts was efficiently led to maremycin A (4) and maremycin D, (8). High optical purity of 4 was confirmed by chiral HPLC comparison with ent-4 prepared from ent-15 and 13.

  DOI：

  10.3987/com-14-s(k)93
• 作为产物：
  描述：

  3-hydroxy-1-methyl-3-(1-methyl-2-oxo-2-phenylethyl)-1,3-dihydro-2H-indol-2-one 在 硫酸 作用下， 以 甲苯 为溶剂， 反应 49.17h， 生成 (2'R,3S,3a'S,7'S)-1,2'-dimethyl-7'-phenyl-6',7'-dihydrospiro[indole-3,3'-isoxazolo[3,2-c][1,4]oxazine]-2,4'(1H,3a'H)-dione
  参考文献：
  名称：

  Total Synthesis of Maremycins A and D1 Using Chiral and Cyclic Nitrone with (E)-3-Ethylidene-1-methylindolin-2-one

  摘要：

  Total syntheses of maremycin A (4) and maremycin D, (8) were described, featuring 1,3-dipolar cycloaddition of a chiral cyclic nitrone 15 with (E)-3-ethylidene-1-methylindolin-2-one (13). The cycloaddition was reversible, especially at high temperature in the presence of a Lewis acid or in a solvent possessing a high acceptor number. One of the cycloadducts was efficiently led to maremycin A (4) and maremycin D, (8). High optical purity of 4 was confirmed by chiral HPLC comparison with ent-4 prepared from ent-15 and 13.

  DOI：

  10.3987/com-14-s(k)93

文献信息

• Synthesis of Maremycins A and D₁ via Cycloaddition of a Nitrone with (<i>E</i>)-3-Ethylidene-1-methylindolin-2-one
  作者：Tohru Ueda、Mitsuhide Inada、Iwao Okamoto、Nobuyoshi Morita、Osamu Tamura

  DOI：10.1021/ol800515w

  日期：2008.5.1

  A concise synthesis of maremycins A and D-1 has been accomplished via cycloaddition of a chiral cyclic nitrone with (E)-3-ethylidene-1-methylindolin-2-one as a key step. This synthesis clarifies the stereochemistry of the maremycins and is suitable for large-scale synthesis for biological screening.
• Total Synthesis of Maremycins A and D1 Using Chiral and Cyclic Nitrone with (E)-3-Ethylidene-1-methylindolin-2-one
  作者：Osamu Tamura、Tohru Ueda、Mitsuhide Inada、Nobuyoshi Morita

  DOI：10.3987/com-14-s(k)93

  日期：——

  Total syntheses of maremycin A (4) and maremycin D, (8) were described, featuring 1,3-dipolar cycloaddition of a chiral cyclic nitrone 15 with (E)-3-ethylidene-1-methylindolin-2-one (13). The cycloaddition was reversible, especially at high temperature in the presence of a Lewis acid or in a solvent possessing a high acceptor number. One of the cycloadducts was efficiently led to maremycin A (4) and maremycin D, (8). High optical purity of 4 was confirmed by chiral HPLC comparison with ent-4 prepared from ent-15 and 13.