Page 207 - 《精细化工》2023年第11期

第 11 期 董向涛，等: 含氨基酸结构的磺酰胺衍生物合成与生物活性 ·2519·

J=12.4 Hz, CH 3), 1.01 (d, 6H, J= 7.6 Hz, 2CH 3); MHz, CDCl 3), δ: 171.4, 158.8, 141.3, 139.9, 139.4,
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CNMR (100 MHz, CDCl 3), δ: 171.5, 159.1, 140.1, 131.9, 129.9, 128.4, 126.8, 124.4, 121.8, 115.5, 115.3,
139.6, 134.2, 132.2, 128.6, 128.5, 128.4, 128.3, 128.2, 63.9, 63.6, 55.0, 50.3, 24.0, 23.0, 20.7, 16.3, 15.9;
+
126.6, 63.9, 63.3, 53.2, 50.2, 30.7, 18.3, 18.1, 16.4, 16.1; ESI-MS, m/Z: [M+H] 理论值 515.2，实测值 515.2。
+
ESI-MS, m/Z: [M+H] 理论值 483.2，实测值 483.3。 {(4-氟苯基) [2-(苯基磺酰氨基)异己酰氨基]甲基}膦酸
{(2-氟苯基) [2-(苯基磺酰氨基)异戊酰氨基]甲基}膦酸 二乙酯（Ⅲl）：白色固体，收率73%，m.p. 178~179 ℃。
二乙酯（Ⅲh）：白色固体，收率61%，m.p. 182~184 ℃。 1 HNMR (400 MHz, CDCl 3), δ: 8.22 (d, 1H, J=10.0 Hz,
1
HNMR (400 MHz, CDCl 3), δ: 8.21 (b, 1H, NH), NH), 7.54~7.62 (m, 2H, ArH), 7.30~7.31 (m, 2H, ArH),
7.61~7.67 (m, 2H, ArH), 7.45~7.52 (m, 1H, ArH), 7.10~7.14 (m, 3H, ArH), 6.92~7.03 (m, 3H, ArH), 5.79
7.25~7.30 (m, 1H, ArH), 6.95~7.11 (m, 5H, ArH), 6.82 (s, 1H, NH), 5.26~5.43 (m, 1H, PCH), 4.07~4.17 (m, 2H,
(s, 1H, NH), 5.69~5.78 (m, 1H, PCH), 3.97~4.14 (m, 3H, OCH 2), 3.90~4.04 (m, 2H, COCH+OCH 2), 3.68~3.88 (m,
COCH+OCH 2), 3.91~3.98 (m, 1H, OCH 2), 3.71~3.79 (m, 1H, OCH 2), 1.25~1.45 (m, 5H, CH 2+CH 3), 1.06~1.13 (m,
1H, OCH 2), 2.10~2.17 (m, 1H, CCHC), 1.32 (t, 3H, 3H, CH 3), 0.77~0.79 (m, 3H, CH 3) 0.54~0.67 (m, 3H,
13
J=12.0 Hz, CH 3), 1.03 (t, 3H, J=12.0 Hz, CH 3), 0.98 (d, CH 3); CNMR (101 MHz, CDCl 3), δ: 171.7, 161.2,
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6H, J= 7.2 Hz, 2CH 3); CNMR (100 MHz, CDCl 3), δ: 140.1, 139.7, 132.2, 132.1, 130.3, 130.1, 128.5, 126.7,
171.4, 158.8, 140.1, 139.4, 129.8, 129.6, 128.4, 126.7, 126.4, 115.5, 115.3, 64.1, 63.5, 55.0, 49.5, 23.0, 22.8,
+
126.6, 124.3, 121.9, 121.7, 115.3, 63.7, 63.6, 53.1, 51.9, 20.8, 16.4, 16.0; ESI-MS, m/Z: [M+H] 理论值 515.2，
+
30.6, 18.4, 18.1, 16.2, 15.9; ESI-MS, m/Z: [M+H] 理论 实测值 515.1。
值 501.2，实测值 501.2。 {(苯基) [2-(苯基磺酰氨基)乙酰氨基]甲基}膦酸二乙酯
1
{(4-氟苯基) [2-(苯基磺酰氨基)异戊酰氨基]甲基}膦酸 （Ⅲm）：白色固体，收率60%，m.p. 172~174 ℃。HNMR
二乙酯（Ⅲi）：白色固体，收率78%，m.p. 190~191 ℃。 (400 MHz, CDCl 3), δ: 8.63 (d, 1H, J=12.0 Hz, NH),
1
HNMR (400 MHz, CDCl 3), δ: 8.12 (b, 1H, NH), 7.47~7.52 (m, 2H, ArH), 7.22~7.32 (m, 5H, ArH),
7.51~7.58 (m, 2H, ArH), 7.35~7.44 (m, 1H, ArH), 7.01~7.19 (m, 3H, ArH), 6.27 (s, 1H, NH), 5.34~5.54(m,
7.15~7.21 (m, 1H, ArH), 6.94~7.15 (m, 5H, ArH), 6.08 1H, PCH), 4.11~4.24 (m, 2H, OCH 2), 3.87~3.92 (m, 1H,
(s, 1H, NH), 5.32~5.44 (m, 1H, PCH), 4.06~4.17 (m, 3H, OCH 2), 3.61~3.73 (m, 3H, NCH 2+OCH 2), 1.33 (t, 3H,
COCH+OCH 2), 3.89~3.92 (m, 1H, OCH 2), 3.71~3.78 (m, J=16.0 Hz, CH 3), 1.04 (m, 3H, J=16.0 Hz, CH 3);
1H, OCH 2), 2.11~2.16 (m, 1H, CCHC), 1.29 (t, 3H, 13 CNMR (101 MHz, CDCl 3), δ: 167.6, 157.7, 139.2,
J=11.6 Hz, CH 3), 1.08 (t, 3H, J=11.6 Hz, CH 3) , 1.05 (d, 132.5, 128.9, 128.6, 128.5, 128.3, 128.2, 128.1, 126.9,
13
6H, J=7.6 Hz, 2CH 3); CNMR (100 MHz, CDCl 3), δ: 125.5, 94.0 , 63.5, 49.2, 45.3, 16.4, 16.1; ESI-MS, m/Z:
+
171.6, 161.2, 140.2, 132.3, 130.2, 130.1, 130.0, 129.8, [M+H] 理论值 441.1，实测值 441.0。
128.7, 128.6, 126.6, 115.5, 115.3, 63.7, 63.5, 53.3, 51.9, {(2-氟苯基) [2-(苯基磺酰氨基)乙酰氨基]甲基}膦酸二
+
30.7, 18.3, 18.1, 16.3, 16.0; ESI-MS, m/Z: [M+H] 理论 乙酯（Ⅲn）：白色固体，收率76%，m.p. 159~160 ℃。
值 501.2，实测值 501.1。 1 HNMR (400 MHz, CDCl 3), δ: 8.61 (d, 1H, J=8.4 Hz,
{(苯基) [2-(苯基磺酰氨基)异己酰氨基]甲基}膦酸二乙 NH), 7.69~7.71 (d, 2H, ArH), 7.47~7.50 (m, 1H, ArH),
1
酯（Ⅲj）：白色固体，收率72%，m.p. 177~178 ℃。HNMR 7.36~7.39 (m, 1H, ArH), 7.25~7.29 (m, 3H, ArH),
(400 MHz, CDCl 3), δ: 8.26 (d, 1H, J=8.8 Hz, NH), 7.02~7.08 (m, 2H, ArH), 6.24~6.27 (s, 1H, NH),
7.52~7.59 (m, 2H, ArH), 7.27~7.33 (m, 5H, ArH), 5.76~5.84 (m, 1H, PCH), 4.08~4.19 (m, 2H, OCH 2),
6.89~7.09 (m, 3H, ArH), 5.53 (s, 1H, NH), 5.24~5.41 (m, 3.87~3.96 (m, 1H, OCH 2), 3.71~3.79 (m, 1H, OCH 2),
1H, PCH), 4.11~4.19 (m, 2H, OCH 2), 3.90~3.99 (m, 2H, 3.67~3.68 (t, 2H, NCH 2+OCH 2), 1.28 (t, 3H, J=12.4 Hz,
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COCH+OCH 2), 3.61~3.82 (m, 1H, OCH 2), 1.23~1.47 (m, CH 3), 1.04 (t, 3H, J=13.2 Hz, CH 3); CNMR (101 MHz,
5H, CH 2+CH 3), 1.03~1.10 (m, 3H, CH 3), 0.78~0.88 (m, CDCl 3), δ: 167.7, 158.8, 139.8, 132.6, 130.1, 130.0,
13
3H, CH 3) 0.54~0.77 (m, 3H, CH 3); CNMR (101 MHz, 129.5, 128.9, 126.9, 124.4, 122.0, 121.9, 115.4, 64.0,
+
CDCl 3), δ: 171.6, 158.7, 139.9, 139.5, 134.1, 132.0, 63.8 , 45.3, 42.3, 16.3, 16.0; ESI-MS, m/Z: [M+H] 理
128.7, 128.5, 128.4, 128.2, 128.1, 126.6, 126.5, 63.6, 论值 459.1，实测值 459.1。
63.3, 55.0, 50.3, 24.0, 23.0, 20.6, 16.4, 15.9; ESI-MS, {(4-氟苯基) [2-(苯基磺酰氨基)乙酰氨基]甲基}膦酸二
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m/Z: [M+H] 理论值 497.2，实测值 497.3。 乙酯（Ⅲo）：白色固体，收率65%，m.p. 153~155 ℃。
{(2-氟苯基) [2-(苯基磺酰氨基)异己酰氨基]甲基}膦酸 1 HNMR (400 MHz, CDCl 3), δ: 8.62 (d, 1H, NH),
二乙酯（Ⅲk）：白色固体，收率69%，m.p. 170~172 ℃。 7.70~7.72 (d, 2H, ArH), 7.28~7.44 (m, 5H, ArH),
1
HNMR (400 MHz, CDCl 3), δ: 8.14 (d, 1H, J=10.0 Hz, 6.95~6.99 (m, 2H, ArH), 6.23 (s, 1H, NH), 5.38~5.46 (m,
NH), 7.45~7.55 (m, 3H, ArH), 7.33 (m, 1H, ArH), 1H, PCH), 4.05~4.15 (m, 2H, OCH 2), 3.85~3.93 (m, 1H,
7.01~7.09 (m, 3H, ArH), 6.95~6.99 (m, 3H, ArH), OCH 2), 3.62~3.75 (m, 3H, NCH 2+OCH 2), 1.26 (t, 3H,
13
5.63~5.80 (m, 1H, PCH), 5.51 (s, 1H, NH), 4.13~4.21 (m, J=12.8 Hz, CH 3), 1.06 (t, 3H, J=15.2 Hz, CH 3); CNMR
2H,OCH 2), 3.75~4.04 (m, 3H, COCH+OCH 2), 1.31~1.47 (101 MHz, CDCl 3), δ: 167.7, 163.6, 141.0, 139.2, 132.6,
(m, 5H, CH 2+CH 3), 1.05~1.11 (m, 3H, CH 3), 0.78~0.81 130.3, 130.2, 130.0, 129.9, 128.9, 126.9, 115.6, 115.4,
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(m, 3H, CH 3) 0.57~0.65 (m, 3H, CH 3); CNMR (101 63.9, 63.7, 48.4, 45.3, 16.4, 16.1; ESI-MS, m/Z: [M+H] +