Hóa hữu cơ bai giang

Hóa Hữu Cơ Organic ChemistryTS... iso-Menthol e,e,a Menthol e,e,eCH3 CHCH32OH CH3 neo-Menthol e,a,e neoiso-Menthol e,a,a... Caran T huyan Pinan Camphan iso-CamphanFenchan iso-BornilanIso

Hóa Hữu Cơ Organic Chemistry

TS Ph m Ng c Tu n Anh ạ ọ ấ

(1R,5R)-(+)-α-pinen (1S,5S)-(−)-α-pinen

Terpen

Isopren

Đầ u Đuô i Đầ u Đuô i

Monoterpen +

O

+ 2HCHO+

Myrcen

Aceton Cetodialdehyd Aldehyd formic

12

34

H2C C

H3C CH3

OH C

HC NaNH2

(+)-Citronellol (−)-citronellol (+)- Citronellol

3,7-Dimethyloct-6-en-1-ol 3,7-dimethyloct-6-en-1-al

Cymbopogon citratus

CH3H

CH3H

CH3

CH3

CH3

C O

CH3

- H2O

+ (CH3)2 CO

CHO

Các giai đoạn tổng hợp

Ionon citral và aceton

CaO

6 5 5

4 4

3

1 1

4 8

7 1

7 6 5

4 3

2 1

9

1,8-p-metadien

Δ1,8-p-mentadien

1,4(8)-p-metadien Δ1,4(8)-p-mentadien

Monoterpen 1 vòng

Limonen

Cl

Cl + 2 HCl

2,3-Epoxy-cineol-1,4

Monoterpen 1 vòng

43

Monoterpen 1 vòng

iso-Menthol (e,e,a) Menthol (e,e,e)

CH3

CH(CH3)2OH

CH3

neo-Menthol (e,a,e) neoiso-Menthol (e,a,a)

Monoterpen 1 vòng

cấu dạng ghế

(1R,2S,5R)-2-Isopropyl-5-methylcyclohexanol

Caran T huyan Pinan Camphan iso-CamphanFenchan iso-BornilanIsocamphan Isobornilan

Monoterpen 2 vòng

4 5

6 7

1

2

3

4 5

6 7

1

2

3

4 5

7 8

6 7

1

2

3

4 5

7 8

9

10

β-pinen

2,6,6-trimethylbicyclo[3.1.1]hept-2-en

β-pinen

6

7

8 9

10

1

2 3 4

5 6

Chuyeå n vò Wagner

Cl + Cl-

- H2O

TiO2

CH3

CH3

OH H

(+)-Camphor (-)-Camphor

(+)-Borneol (-)-Isoborneol (+)-Isoborneol (-)-Borneol

endo exo

Monoterpen 2 vòng

Nhóm Camphan

(+)-3-Bromo-8-camphorsulfonic Acid

S S

R R

(1R)-(+)-Camphor

3,7,11-Trimethyl-1,3,6,10-dodecatetraen

α-Farnesen(3E,6E)

(3Z,6E)

o Sesquiterpen không vòng

o Sesquiterpen 1 vòng

Germacran Humulan

Eleman Bisabolan

Zingiberen

1 2 3

4 5

6

7 10

24

15

19 23

22

1

2 3

4 5

6

7 9

8

8 9

10

14 15

18 19

H

H H

H

H H

H H

H

H H

H H

H

H

H H

H

H H

H H

Astaxanthin

Licopen

H

H H

H

H H

H

H H

Licopen

Retinol

Steroid

Gonan

2,3,4,5,6,7,8,9,10,11,12,13,14,15,16,17-Hexadecahydro-1H-cyclopenta[a]phenanthrenTetracyclo[8.7.0.02,7.011,15]heptadecan

Steran (Gonan) Estran Androstan

Pregnan Cholan Cholestan

9 1414

Cholestan Coprostan

A/B trans A/B cisB/C trans B/C transC/D trans C/D transDãy 5α (dãy normal) Dãy 5β (dãy allo)

o Acid mật

Acid cholic

3α,7α,12α-Trihydroxy-5β-cholanoic acid

o Hormon

o Hormon