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HRID1399550

反应详情

EQUATION

反应方程式

HRID 1399550 的结构方程式

REACTANTS

反应物

3
结构：CS(N)(=O)=O
HCID72879

Methanesulfonamide

CH5NO2S

结构：CC[C@H]1CN2CC[C@H]1C[C@@H]2[C@@H](Oc1nnc(O[C@@H](c2ccnc3ccc(OC)cc23)[C@H]2C[C@@H]3CCN2C[C@@H]3CC)c2ccccc12)c1ccnc2ccc(OC)cc12
HCID11217202

(DHQD)2PHAL

C48H54N6O4

结构：C/C=C(\O[Si](C)(C)C(C)(C)C)c1cccc([N+](=O)[O-])c1
HCID46838067

未命名化合物

PRODUCTS

生成物

1
结构：C[C@@H](O)C(=O)c1cccc([N+](=O)[O-])c1
HCID46838208

未命名化合物

收率 75.9%

AUXILIARIES

试剂、催化剂与溶剂

1
结构：CC(C)(C)O.O
溶剂HCID71401949

2-Methylpropan-2-ol--water (1/1)

C4H12O2

PROCEDURE

实验过程

Compound 10g was synthesized by a procedure similar to that described for (R)-10a using (Z)-tert-butyl(1-(3-nitrophenyl)prop-1-enyloxy)dimethylsilane, (9g, 8.0 g, 0.027 mol), AD-mix-β (38 g), and CH3SO2NH2 (2.64 g, 0.0277 mol) in tert-butyl alcohol-water (110 mL:110 mL). The reaction was quenched with sodium sulfite (27.4 g). After purification by column chromatography on silica gel, 4.0 g (75%) of the desired product was isolated: [α]20D +63.8° (c 1.3, CHCl3); 1H NMR (CDCl3) δ 8.80-8.74 (m, 1H), 8.52-8.44 (m, 1H), 8.31-8.24 (m, 1H), 7.83-7.68 (m, 1H), 5.27-5.13 (m, 1H), 3.59 (d, 1H, J=6.5 Hz), 1.49 (d, 3H, J=7.08 Hz); 13C NMR (CDCl3) δ 200.4, 148.6, 134.9, 134.1, 130.2, 128.1, 121.6, 69.8, 21.9; C9H9NO4.

WORKUP

后处理

  1. customCompound 10g was synthesized by a procedure similar to
  2. customThe reaction was quenched with sodium sulfite (27.4 g)
  3. customAfter purification by column chromatography on silica gel