Page 237 - 《精细化工》2023年第4期

す 4 ᱌ 䧌⦉㏏喑ぶ: CuI ϸᄩ Reformatsky ࣺᏁ倅᩵व᜽ ȕ-㓌ധ䚜ㆨࡃव➖ g923g

MHz, CDCl 3 ), į: 164.06 (O==C), 163.74 (Ar-C), թ 223.13ȡ
163.44 (Ar-C), 134.62 (Ar-C), 129.21 (Ar-C), 128.41 3-㓌ധ-3-(4-⩟⅔㠜ധ)̮䚥Ά䚜喍18喎喟ᬍ㞟⇦
(Ar-C), 127.76 (Ar-C), 116.46 (Ar-C), 113.91 (Ar-C), [35] 1
111.36 (Ar-C), 73.95 (COH), 73.69 (CF 2 O), 73.43 ⟣➖ 喑209.5 mg喑ϔ⢴ 88%ȡ HNMR (400 MHz,
(CF 2 O), 63.23 (OCH 2 ), 13.77 (CH 3 )ȡESI-MS, m/Z喟 CDCl 3 ), į: 7.32~7.26 (m, 2H, Ar-H), 6.87~6.72 (m,
+
[M+H] ⤳䃧թ 231.06喠჋≸թ 231.08ȡ 2H, Ar-H), 4.29 (s, 1H, OH), 3.99 (q, J = 7.2 Hz, 2H,
OCH 2 ), 3.72 (s, 3H, OCH 3 ), 2.91~2.64 (m, 2H, CH 2 ),
3-㓌ധ-3-㠜ധ̮䚥Ά䚜喍14喎喟叱㞟⇦⟣➖ [33] 喑 1.45 (s, 3H, COHCH 3 ), 1.07 (t, J = 7.2 Hz, 3H, CH 3 )ȡ
1
195.5 mg喑ϔ⢴ 94%ȡ HNMR (400 MHz, CDCl 3 ), į: 13 CNMR (101 MHz, CDCl 3 ), į: 172.81 (O==C),
7.47~7.42 (m, 2H, Ar-H), 7.34~7.31 (m, 2H, Ar-H), 158.39 (Ar-C), 139.07 (Ar-C), 125.68 (Ar-C), 113.53
7.26~7.20 (m, 1H, Ar-H), 4.43 (s, 1H, OH), 4.04 (q, J (Ar-C), 72.51 (COH), 60.74 (CH 2 O), 55.24 (OCH 3 ),
= 7.2 Hz, 2H, OCH 2 ), 3.00~2.74 (m, 2H, CH 2 ), 1.54 (s, 46.51 (CH 2 CO), 30.78 (COHCH 3 ), 14.05 (CH 3 )ȡESI-
13
3H, COHCH 3 ), 1.12 (t, J = 7.2 Hz, 3H, CH 3 )ȡ CNMR MS, m/Z喟[M+H] ⤳䃧թ 239.11喠჋≸թ 239.13ȡ
+
(101 MHz, CDCl 3 ), į: 172.75 (O==C), 146.86 (Ar-C), 3-㓌ധ-3-(2,5-ι⩟ധ㠜ധ)̮䚥Ά䚜喍19喎喟ᬍ
128.26 (Ar-C), 126.87 (Ar-C), 124.49 (Ar-C), 72.78
1
(COH), 60.76 (CH 2 O), 46.44 (CH 2 CO), 30.68 㞟⇦⟣➖ [36] 喑200.5 mg喑ϔ⢴ 85%ȡHNMR (400 MHz,
+
(COHCH 3 ), 14.01 (CH 3 )ȡESI-MS, m/Z喟[M+H] ⤳䃧 CDCl 3 ), į: 7.17 (s, 1H, Ar-H), 6.95~6.93 (m, 1H,
Ar-H), 6.87~6.86 (m, 1H, Ar-H), 4.29 (s, 1H, OH),
թ 209.11喠჋≸թ 209.12ȡ
4.07~3.93 (m, 2H, OCH 2 ), 2.91~2.73 (m, 2H, CH 2 ),
3-㓌ധ-3-(2-⩟㠜ധ)̮䚥Ά䚜喍15喎喟ᬍ㞟⇦⟣ 2.43 (s, 3H, Ar-CH 3 ), 2.21 (s, 3H, Ar-CH 3 ), 1.52 (s,
1
➖喑197.5 mg喑ϔ⢴ 89%ȡHNMR (400 MHz, CDCl 3 ), 3H, COHCH 3 ), 1.07 (t, J = 7.1 Hz, 3H, CH 3 )ȡ CNMR
13
į: 7.35~27.33 (m, 1H, Ar-H), 7.06~7.05 (m, 3H, Ar-H), (101 MHz, CDCl 3 ), į: 173.02 (O==C), 143.56 (Ar-C),
4.31 (s, 1H, OH), 4.06~3.95 (m, 2H, OCH 2 ), 135.02 (Ar-C), 132.75 (Ar-C), 131.99 (Ar-C), 127.81
3.15~2.90 (m, 2H, CH 2 ), 2.49 (s, 3H, Ar-CH 3 ), 1.53 (s, (Ar-C), 126.19 (Ar-C), 74.05 (COH), 60.70 (CH 2 O),
13
3H, COHCH 3 ), 1.07 (t, J = 7.1 Hz, 3H, CH 3 )ȡ CNMR 45.75 (CH 2 CO), 28.89 (COHCH 3 ), 21.91 (Ar-CH 3 ),
(101 MHz, CDCl 3 ), į: 172.98 (O==C), 143.74 (Ar-C), 21.18 (Ar-CH 3 ), 14.06 (CH 3 )ȡESI-MS, m/Z喟[M+H] +
135.37 (Ar-C), 132.80 (Ar-C), 127.21 (Ar-C), 125.75 ⤳䃧թ 237.14喠჋≸թ 237.15ȡ
(Ar-C), 125.38 (Ar-C), 74.14 (COH), 60.76 (CH 2 O),
45.76 (CH 2 CO), 28.91 (Ar-CH 3 ), 22.35 (COHCH 3 ), 3-㓌ധ-3-(2-⅜㠜ധ)̮䚥Ά䚜喍20喎喟ᬍ㞟⇦⟣
1
+
14.03 (CH 3 )ȡESI-MS, m/Z喟[M+H] ⤳䃧թ 223.11喠 ➖ [34] 喑220.1 mg喑ϔ⢴ 91%ȡHNMR (400 MHz, CDCl 3),
į: 7.78~7.77 (m, 1H, Ar-H), 7.28~7.16 (m, 2H, Ar-H),
჋≸թ 223.13ȡ
7.10~7.08 (m, 1H, Ar-H), 4.62 (s, 1H, OH), 3.94 (q, J
3-㓌ധ-3-(3-⩟㠜ധ)̮䚥Ά䚜喍16喎喟ᬍ㞟⇦⟣ = 7.1 Hz, 2H, OCH 2 ), 3.18~2.88 (m, 2H, CH 2 ), 1.64 (s,
1
➖ [34] 喑195.4 mg喑ϔ⢴ 88%ȡ HNMR (400 MHz, 3H, COHCH 3 ), 1.00 (t, J = 7.1 Hz, 3H, CH 3 )ȡ CNMR
13
CDCl 3 ), į: 7.20 (s, 1H, Ar-H), 7.12~7.09 (m, 2H, (101 MHz, CDCl 3 ), į: 172.96 (O==C), 142.92 (Ar-C),
Ar-H), 6.95~6.94 (m, 1H, Ar-H), 4.32 (s, 1H, OH), 131.19 (Ar-C), 130.44 (Ar-C), 128.59 (Ar-C), 128.04
3.96 (q, J = 7.2 Hz, 2H, OCH 2 ), 2.90~2.64 (m, 2H, (Ar-C), 126.97 (Ar-C), 73.10 (COH), 60.74 (CH 2 O),
CH 2 ), 2.25 (s, 3H, Ar-CH 3 ), 1.44 (s, 3H, COHCH 3 ), 43.77 (CH 2 CO), 27.20 (COHCH 3 ), 13.93 (CH 3 )ȡ
13
1.04 (t, J = 7.2 Hz, 3H, CH 3 )ȡ CNMR (101 MHz, ESI-MS, m/Z喟[M+H] ⤳䃧թ 243.08喠჋≸թ 243.09ȡ
+
CDCl 3 ), į: 172.76 (O==C), 146.90 (Ar-C), 137.76
(Ar-C), 128.14 (Ar-C), 127.60 (Ar-C), 125.26 (Ar-C), 3-㓌ധ-3-(4-⅜㠜ധ)̮䚥Ά䚜喍21喎喟ᬍ㞟⇦⟣
1
121.53 (Ar-C), 72.73 (COH), 60.69 (CH 2 O), 46.45 ➖ [28] 喑217.9 mg喑ϔ⢴ 93%ȡHNMR (400 MHz, CDCl 3),
(CH 2 CO), 30.67 (Ar-CH 3 ), 21.63 (COHCH 3 ), 14.03 į: 7.35~7.27 (m, 2H, Ar-H), 7.25~7.19 (m, 2H, Ar-H),
+
(CH 3 )ȡESI-MS, m/Z喟[M+H] ⤳䃧թ 223.11喠჋≸ 4.39 (s, 1H, OH), 4.00 (q, J = 7.2 Hz, 2H, OCH 2 ),
թ 223.13ȡ 2.90~2.67 (m, 2H, CH 2 ), 1.44 (s, 3H, COHCH 3 ), 1.08
13
3-㓌ധ-3-(4-⩟㠜ധ)̮䚥Ά䚜喍17喎喟ᬍ㞟⇦⟣ (t, J = 7.2 Hz, 3H, CH 3 )ȡ CNMR (101 MHz, CDCl 3 ),
1
➖ [28] 喑199.8 mg喑ϔ⢴ 90%ȡ HNMR (400 MHz, į: 172.62 (O==C), 145.46 (Ar-C), 132.70 (Ar-C),
128.37 (Ar-C), 126.06 (Ar-C), 72.51 (COH), 60.93
CDCl 3 ), į: 7.26 (d, J = 8.0 Hz, 2H, Ar-H), 7.07 (d, J = (CH 2 O), 46.18 (CH 2 CO), 30.67 (COHCH 3 ), 14.02
8.0 Hz, 2H, Ar-H), 4.29 (s, 1H, OH), 4.05~3.92 (m, +
2H, OCH 2 ), 2.92~2.67 (m, 2H, CH 2 ), 2.25 (s, 3H, (CH 3 )ȡESI-MS, m/Z喟[M+H] ⤳䃧թ 243.08喠჋≸
Ar-CH 3 ), 1.45 (s, 3H, COHCH 3 ), 1.08 (t, J = 7.2 Hz, թ 243.10ȡ
13
3H, CH 3 )ȡ CNMR (101 MHz, CDCl 3 ), į: 172.81 3-㓌ധ-3-(2-⅌㠜ധ)̮䚥Ά䚜喍22喎喟ᬍ㞟⇦⟣
1
(O==C), 143.95 (Ar-C), 136.41 (Ar-C), 128.95 (Ar-C), ➖ [37] 喑203.4 mg喑ϔ⢴ 90%ȡ HNMR (400 MHz,
124.38 (Ar-C), 72.66 (COH), 60.73 (CH 2 O), 46.41 CDCl 3 ), į: 7.60~7.58 (m, 1H, Ar-H), 7.19~7.12 (m,
(CH 2 CO), 30.77 (ArCH 3 ), 20.98 (COHCH 3 ), 14.04 1H, Ar-H), 7.07~7.05 (m, 1H, Ar-H), 6.96~6.87 (m,
+
(CH 3 )ȡESI-MS, m/Z喟[M+H] ⤳䃧թ 223.11喠჋≸ 1H, Ar-H), 4.54 (s, 1H, OH), 3.95 (q, J = 7.1 Hz, 2H,