[ CAS No. 150-84-5 ] {[proInfo.proName]}

Name: 150-84-5|3,7-Dimethyloct-6-en-1-yl acetate|95%
Brand: Ambeed
SKU: A522404
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Quality Control of [ 150-84-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 150-84-5 ]

Product Details of [ 150-84-5 ]

CAS No. :	150-84-5	MDL No. :	MFCD00015039
Formula :	C₁₂H₂₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JOZKFWLRHCDGJA-UHFFFAOYSA-N
M.W :	198.30	Pubchem ID :	9017
Synonyms :

Calculated chemistry of [ 150-84-5 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.75
Num. rotatable bonds :	7
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	60.61
TPSA :	26.3 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.33 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.29
Log Po/w (XLOGP3) :	4.48
Log Po/w (WLOGP) :	3.32
Log Po/w (MLOGP) :	3.04
Log Po/w (SILICOS-IT) :	3.14
Consensus Log Po/w :	3.46

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.43
Solubility :	0.0737 mg/ml ; 0.000372 mol/l
Class :	Soluble
Log S (Ali) :	-4.75
Solubility :	0.00351 mg/ml ; 0.0000177 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-2.88
Solubility :	0.261 mg/ml ; 0.00132 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	2.69

Safety of [ 150-84-5 ]

Signal Word:	Danger	Class:	9
Precautionary Statements:	P501-P273-P260-P270-P264-P280-P391-P314-P337+P313-P305+P351+P338-P301+P312+P330	UN#:	3082
Hazard Statements:	H302-H319-H372-H410	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 150-84-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 150-84-5 ]

[ 150-84-5 ] Synthesis Path-Downstream 1~87

1
[ 150-84-5 ]
(+/-)-6-acetoxy-4-methylhexanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With ozone In ethyl acetate
	Multi-step reaction with 2 steps 1.1: oxygen / dichloromethane / 0.5 h / -78 °C 1.2: 2 h / 25 °C 2.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; disodium hydrogenphosphate; sodium hypochlorite; sodium chloride / acetonitrile; water / 3 h / 35 °C

Reference： [1]Beckwith,A.L.J. et al. [Australian Journal of Chemistry, 1977, vol. 30, p. 2177 - 2188]
[2]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - WO2021/225968, 2021, A1

2
[ 150-84-5 ]
[ 26759-58-0 ]

Yield	Reaction Conditions	Operation in experiment
97%	With N-methyl-2-indolinone In water; acetone; <i>tert</i>-butyl alcohol at 20℃; for 36h;
67%	With ruthenium trichloride; sodium periodate In water; ethyl acetate; acetonitrile at 0℃; for 0.05h;
67%	With ruthenium trichloride; sodium periodate In ethyl acetate; acetonitrile for 0.05h;

With tert.-butylhydroperoxide; osmium(VIII) oxide; tetraethylammonium chloride; sodium acetate In acetone; <i>tert</i>-butyl alcohol

Reference： [1]Huang, Yangen; Meng, Wei-Dong; Qing, Feng-Ling [Tetrahedron Letters, 2004, vol. 45, # 9, p. 1965 - 1968]
[2]Shing, Tony K. M.; Tai, Vincent W.-F.; Tam, Eric K. W. [Angewandte Chemie, 1994, vol. 106, # 22, p. 2408 - 2409]
[3]Shing, Tony K. M.; Tam, Eric K. W.; Tai, Vincent W.-F.; Chung, Ivan H. F.; Jiang, Qin [Chemistry - A European Journal, 1996, vol. 2, # 1, p. 50 - 57]
[4]Akashi,K. et al. [Journal of Organic Chemistry, 1978, vol. 43, # 10, p. 2063 - 2066]

3
[ 150-84-5 ]
[ 60857-06-9 ]

Yield	Reaction Conditions	Operation in experiment
40%	With tert.-butylhydroperoxide; dipyridinium dichromate In benzene at 25℃; for 11h;
	(i) tBuOH, CrO₃, CCl₄, (ii) /BRN= 1723886/, Ac₂O, AcOH; Multistep reaction;

Reference： [1]Chidambaram, Nallaperumal; Chandrasekaran, Srinivasan [Journal of Organic Chemistry, 1987, vol. 52, # 22, p. 5048 - 5051]
[2]Patel,J.S. et al. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1978, vol. 16, p. 188 - 190]

4
[ 150-84-5 ]
[ 922-67-8 ]
[ 71708-03-7 ]

Yield	Reaction Conditions	Operation in experiment
	With aluminium trichloride In benzene

Reference： [1]Snider,B.B.; Rodini,D. [Tetrahedron Letters, 1978, p. 1399 - 1400]

5
[ 150-84-5 ]
[ 922-67-8 ]
(E)-9-Acetoxy-4-isopropenyl-7-methyl-non-2-enoic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In benzene

Reference： [1]Snider,B.B. et al. [Journal of the American Chemical Society, 1979, vol. 101, p. 5283 - 5293]

6
[ 908094-01-9 ]
[ 150-84-5 ]
[ 64988-49-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium periodate 1.) CCl₄, CH₃CN, H₂O, 0.5h, 25 deg C, 2.) Et₂O; Yield given. Multistep reaction;

Reference： [1]Carlsen, Per H. J.; Katsuki, Tsutomu; Martin, Victor S.; Sharpless, K. Barry [Journal of Organic Chemistry, 1981, vol. 46, # 19, p. 3936 - 3938]

7
[ 67-56-1 ]
[ 150-84-5 ]
[ 868552-81-2 ]

Yield	Reaction Conditions	Operation in experiment
82%	With diphenyl diselenide; magnesium sulfate at 66 - 68℃; electrolysis under a constant current 6.7 mA/cm²;

Reference： [1]Torii, Sigeru; Uneyama, Kenji; Ono, Michio; Bannou, Tadashi [Journal of the American Chemical Society, 1981, vol. 103, # 15, p. 4606 - 4608]

8
[ 79-43-6 ]
[ 150-84-5 ]
3,7-dimethyloctyl acetate [ No CAS ]
Dichloro-acetic acid 7-acetoxy-1,1,5-trimethyl-heptyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 65% 2: 20%	With triethylsilane; lithium perchlorate at 20℃; for 48h;

Reference： [1]Julia, Marc; Roy, Pierre [Tetrahedron, 1986, vol. 42, # 18, p. 4991 - 5002]

9
[ 50-00-0 ]
[ 150-84-5 ]
[ 84143-54-4 ]

Yield	Reaction Conditions	Operation in experiment
98.5%	With dimethylaluminum chloride In n-heptane; dichloromethane at 0℃; for 1h;

Reference： [1]Snider, Barry B; Phillips, Gary B. [Journal of Organic Chemistry, 1983, vol. 48, # 4, p. 464 - 469]

10
[ 930-68-7 ]
[ 150-84-5 ]
[ 75265-22-4 ]

Yield	Reaction Conditions	Operation in experiment
45%	With ethylaluminum dichloride In n-heptane; benzene at 25℃; for 72h;

Reference： [1]Snider,B.B.; Rodini,D.J.; Straten,J.V. [Journal of the American Chemical Society, 1980, vol. 102, p. 5872]

11
[ 106-22-9 ]
[ 150-84-5 ]

Yield	Reaction Conditions	Operation in experiment
57%	With tin(ll) chloride In water; acetic acid for 17h; Ambient temperature;
	With Pichia kluyveri NBRC 1165; S-acetyl coenzyme A In decane for 288h;	2.6. Transacetylation of citronellol with P. kluyveri NBRC 1165 Microbial transacetylation of citronellol by acetyl-CoA produced viaglucose metabolism was compared between the S-L IBR and L-L IBRtac.P. kluyveri NBRC 1165 was cultivated in 25 ml of the CA-medium at30 °C with rotation (200 rpm) for 1 day as a seed broth.Concerning the S-L IBR, 150 μl of the 1-day seed broth was inoculatedon the CA-agar plate prepared in a glass vial (50 ml; 30mmi.d.) and stationary precultivation was done at 30 °C for 1 day. The samefour reactors were constructed. Three ml of a 10 or 20% solution ofcitronellol in n-decane was added onto a biofilm formed on the agarplate, and incubation was continued for 12 days. The products accumulatedin the organic phase were directly determined by the GLC

Reference： [1]Fischli, Albert; Mueller, Peter Michael [Helvetica Chimica Acta, 1980, vol. 63, # 2, p. 529 - 554]
[2]Oda, Shinobu; Nakanishi, Mami; Ishikawa, Asako; Baba, Toshiki [Process Biochemistry, 2019, vol. 80, p. 1 - 8]

12
[ 616-42-2 ]
[ 150-84-5 ]
methyl 6-acetoxy-1-isopropenyl-4-methylhexylsulfinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With boron trifluoride diethyl etherate at 25℃; for 1h;

Reference： [1]Dragan, V. A.; Moiseenkov, A. M. [Russian Chemical Bulletin, 1993, vol. 42, # 1, p. 95 - 97][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1993, # 1, p. 105 - 107]

13
[ 150-84-5 ]
[ 36336-08-0 ]
3,7-Dimethyl-7-fluoro-6-methoxyoctyl acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	In methanol; chloroform; acetonitrile

Reference： [1]Rozen, Shlomo; Mishani, Eyal; Kol, Moshe; Ben-David, Iris [Journal of Organic Chemistry, 1994, vol. 59, # 15, p. 4281 - 4284]

14
[ 150-84-5 ]
[ 1787-98-0 ]

Yield	Reaction Conditions	Operation in experiment
96%	With (NMe₄)(Co-ortho-phenylenebis(N'-methyloxamidate)2H₂OCH₃CN; oxygen; pivalaldehyde In fluorobenzene for 1.25h; Ambient temperature;
95%	With sodium acetate; bis[3,5-bis(trifluoromethyl)diphenyl] diselenide In 2,2,2-trifluoroethanol at 20℃; for 0.5h;
90%	With <NMe4>2<Ni(Me2opba)>*4H2O; oxygen; pivalaldehyde In fluorobenzene for 2.5h;

65%	With sodium chlorite; edetate disodium In water; acetonitrile at 55 - 65℃; for 15h;
55%	With dihydrogen peroxide In water at 20℃; for 6h; Green chemistry;
94.5 % Chromat.	With oxygen; isobutyraldehyde In 1,2-dichloro-ethane for 3h; Ambient temperature;
95 % Chromat.	With Ni(dmp)2; oxygen; isobutyraldehyde In 1,2-dichloro-ethane for 24h; Ambient temperature;
90 % Turnov.	With <Fe3O(piv)3(MeOH)3>Cl; oxygen at 60℃; for 20h;
81 % Chromat.	With <N,N'-bis(salicylidene-γ-iminopropyl)methylaminato>cobalt (II); oxygen; 2-Methylcyclohexanone at 75℃; for 6h;
86 % Chromat.	With 1,1-diethoxypropane; bis(3-methyl-2,4-pentanedionato)cobalt(II); 4 A molecular sieve; oxygen at 45℃; for 20h;
	With oxygen; isobutyraldehyde In 1,2-dichloro-ethane for 7h; Ambient temperature; Yield given;
82 % Chromat.	With 1,1-diethoxypropane; bis(3-methyl-2,4-pentanedionato)cobalt(II); 4 A molecular sieve; oxygen at 45℃; for 20h;
	Multi-step reaction with 2 steps 1: 1.) I₂, 4 angstroem molecular sieves, 2.) pyridinium chloride / 1.) dry CH₂Cl₂, room temp, 30 min, 2.) 3 h 2: 70 percent / Al₂O₃
	With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃;
	With [((S,S)-N,N′-bis(2-pyridylmethyl)-(S,S)-2,2′-bipyrrolidine)Fe^II(OTf)₂]; dihydrogen peroxide; acetic acid In water; acetonitrile at 0℃; Inert atmosphere; chemospecific reaction;
	With ferredoxin reductase; [2Fe–2S] ferredoxin; cytochrome P₄₅₀ enzyme CYP₁₀₁C₁ In aq. buffer Enzymatic reaction;

Reference： [1]Estrada, Jesus; Fernandez, Isabel; Pedro, Jose R.; Ottenwaelder, Xavier; Ruiz, Rafael; Journaux, Yves [Tetrahedron Letters, 1997, vol. 38, # 13, p. 2377 - 2380]
[2]Ten Brink, Gerd-Jan; Fernandes, Bruno C.M.; Van Vliet, Michiel C.A.; Arends, Isabel W.C.E.; Sheldon, Roger A. [Journal of the Chemical Society. Perkin Transactions 1 (2001), 2001, # 3, p. 224 - 228]
[3]Fernandez, Isabel; Pedro, Jose R.; Rosello, Antonio L.; Ruiz, Rafael; Ottenwaelder, Xavier; Journaux, Yves [Tetrahedron Letters, 1998, vol. 39, # 18, p. 2869 - 2872]
[4]Geng, Xue-Li; Wang, Zhi; Li, Xiao-Qiang; Zhang, Chi [Journal of Organic Chemistry, 2005, vol. 70, # 23, p. 9610 - 9613]
[5]Cunningham, William B.; Tibbetts, Joshua D.; Hutchby, Marc; Maltby, Katarzyna A.; Davidson, Matthew G.; Hintermair, Ulrich; Plucinski, Pawel; Bull, Steven D. [Green Chemistry, 2020, vol. 22, # 2, p. 513 - 524]
[6]Yamada, Tohru; Takai, Toshihiro; Rhode, Oliver; Mukaiyama, Teruaki [Chemistry Letters, 1991, # 1, p. 1 - 4]
[7]Yamada, Tohru; Takai, Toshihiro; Rhode, Oliver; Mukaiyama, Teruaki [Bulletin of the Chemical Society of Japan, 1991, vol. 64, # 7, p. 2109 - 2117]
[8]Ito, Satoru; Inoue, Koh; Mastumoto, Masakatsu [Journal of the American Chemical Society, 1982, vol. 104, # 23, p. 6450 - 6452]
[9]Takai, Toshihiro; Hata, Eiichiro; Yorozu, Kiyotaka; Mukaiyama, Teruaki [Chemistry Letters, 1992, # 10, p. 2077 - 2080]
[10]Mukaiyama, Teruaki; Yorozu, Kiyotaka; Takai, Toshihiro; Yamada, Tohru [Chemistry Letters, 1993, # 3, p. 439 - 442]
[11]Takai, Toshihiro; Hata, Eiichiro; Yamada, Tohru; Mukaiyama, Teruaki [Bulletin of the Chemical Society of Japan, 1991, vol. 64, # 8, p. 2513 - 2518]
[12]Yorozu, Kiyotaka; Takai, Toshihiro; Yamada, Tohru; Mukaiyama, Teruaki [Bulletin of the Chemical Society of Japan, 1994, vol. 67, # 8, p. 2195 - 2202]
[13]Antonioletti, Roberto; D'Auria, Maurizio; Mico, Antonella De; Piancatelli, Giovanni; Scettri, Arrigo [Tetrahedron, 1983, vol. 39, # 10, p. 1765 - 1768]
[14]Location in patent: experimental part Justicia, José; Jiménez, Tania; Morcillo, Sara P.; Cuerva, Juan M.; Oltra, J. Enrique [Tetrahedron, 2009, vol. 65, # 52, p. 10837 - 10841]
[15]Yazerski, Vital A.; Spannring, Peter; Gatineau, David; Woerde, Charlotte H.M.; Wieclawska, Sara M.; Lutz, Martin; Kleijn, Henk; Klein Gebbink, Robertus J.M. [Organic and Biomolecular Chemistry, 2014, vol. 12, # 13, p. 2062 - 2070]
[16]Sarkar, Md. Raihan; Bell, Stephen G. [Catalysis science and technology, 2020, vol. 10, # 17, p. 5983 - 5995]

15
[ 150-84-5 ]
[ 1787-98-0 ]
[ 123074-79-3 ]

Yield	Reaction Conditions	Operation in experiment
1: 40% 2: 40%	With potassium permanganate; water; copper(II) sulfate; <i>tert</i>-butyl alcohol In dichloromethane at 25℃; for 2h;

Reference： [1]Baskaran, Sundarababu; Das, Jagattaran; Chandrasekaran, Srinivasan [Journal of Organic Chemistry, 1989, vol. 54, # 21, p. 5182 - 5184]

16
[ 150-84-5 ]
3,7-dimethyloctyl acetate [ No CAS ]
[ 110109-63-2 ]

Yield	Reaction Conditions	Operation in experiment
1: 1% 2: 90%	With triethylsilane; lithium perchlorate; trifluoroacetic acid In various solvent(s) at 20℃; for 22h;

Reference： [1]Julia, Marc; Roy, Pierre [Tetrahedron, 1986, vol. 42, # 18, p. 4991 - 5002]

17
[ 150-84-5 ]
3-methyl-6-oxohexyl acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With ozone In dichloromethane at -78℃;
90%	With ozone In dichloromethane at -78℃;
88%	Stage #1: citronellyl-acetate With oxygen In dichloromethane at -78℃; for 0.5h; Stage #2: With dimethylsulfide In dichloromethane at 25℃; for 2h;	45 PREPARATION 45: 3-methyl-6-oxohexyl acetate A solution of 3,7-dimethyloct-6-en-1-yl acetate (6 g, 30.26 mmol) in DCM (50 mL) was purged with ozone at -78°C for 30 minutes and then with O2 until there was no ozone observed in the off-gas. Next, Me2S (10.63 g, 171.08 mmol, 12.57 mL) was added and the mixture was stirred at 25°C for 2 hours. TLC (petroleum ether/EtOAc = 5:1, Rf =0.4) indicated the starting material was consumed and one major new spot with larger polarity was detected. The reaction mixture was concentrated under reduced pressure and purified by column chromatography (SiO2) using a gradient of petroleum ether/EtOAc (10:1 to 5:1) to give the title compound as a yellow oil (4.6 g, 88%).1H NMR (CDCl3) δ ppm 9.68 - 9.73 (m, 1H), 3.99 - 4.07 (m, 2H), 2.28 - 2.47 (m, 2H), 1.97 (s, 3H), 1.56 - 1.67 (m, 2H), 1.49 - 1.55 (m, 1H), 1.37 - 1.47 (m, 2H), 0.86 (d, J = 6.4 Hz, 2H), 0.84 (br s, 1H).

88%

Stage #1: citronellyl-acetate With oxygen In dichloromethane at -78℃; for 0.5h; Stage #2: With dimethylsulfide In dichloromethane at 25℃; for 2h;

45 PREPARATION 45: 3-methyl-6-oxohexyl acetate A solution of 3,7-dimethyloct-6-en-1-yl acetate (6 g, 30.26 mmol) in DCM (50 mL) was purged with ozone at -78°C for 30 minutes and then with O2 until there was no ozone observed in the off-gas. Next, Me2S (10.63 g, 171.08 mmol, 12.57 mL) was added and the mixture was stirred at 25°C for 2 hours. TLC (petroleum ether/EtOAc = 5:1, Rf =0.4) indicated the starting material was consumed and one major new spot with larger polarity was detected. The reaction mixture was concentrated under reduced pressure and purified by column chromatography (SiO2) using a gradient of petroleum ether/EtOAc (10:1 to 5:1) to give the title compound as a yellow oil (4.6 g, 88%).1H NMR (CDCl3) δ ppm 9.68 - 9.73 (m, 1H), 3.99 - 4.07 (m, 2H), 2.28 - 2.47 (m, 2H), 1.97 (s, 3H), 1.56 - 1.67 (m, 2H), 1.49 - 1.55 (m, 1H), 1.37 - 1.47 (m, 2H), 0.86 (d, J = 6.4 Hz, 2H), 0.84 (br s, 1H).

Reference： [1]Hon; Lin; Chen [Synthetic Communications, 1993, vol. 23, # 11, p. 1543 - 1553]
[2]Hon, Yung-Son; Lin, Sheng-Wun; Lu, Ling; Chen, Yao-Jung [Tetrahedron, 1995, vol. 51, # 17, p. 5019 - 5034]
[3]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - WO2021/225968, 2021, A1 Location in patent: Paragraph 0221; 0222
[4]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - WO2021/225968, 2021, A1 Location in patent: Paragraph 0221; 0222

18
[ 150-84-5 ]
[ 54702-06-6 ]

Yield	Reaction Conditions	Operation in experiment
60%	With hydrogenchloride In acetic acid at 0℃; for 1h;

Reference： [1]Moiseenkov, A. M.; Dragan, V. A.; Lozanova, A. V.; Veselovskii, V. V. [Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1988, vol. 37, p. 1603 - 1609][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1988, # 8, p. 1797 - 1803]

19
[ 150-84-5 ]
[ 74514-34-4 ]

Yield	Reaction Conditions	Operation in experiment
86%	With sodium chloride In dichloromethane; water for 4h; Ambient temperature; electrolysis by using Pt foils at constant current (50 mA);
84%	With sodium chloride In dichloromethane; water at 25℃; for 0.3h; electrolysis: ruthenium oxide: anode; titanium cylinder: cathode; I = 0.94 A;
67%	With chlorine In tetrachloromethane at 0℃; for 0.583333h;

	In dichloromethane; water at 25℃; for 0.3h; influence of concentration of electrolyte NaCl and reaction time on the product yield;
	With hypochloric acid In dichloromethane
	Multi-step reaction with 2 steps 1: 95 percent / LiClO₄ / CH₂Cl₂ / 0 °C 2: 70 percent / BnEt₃NCl / CHCl₃ / 7 h / Heating

Reference： [1]Torii, Sigeru; Uneyama, Kenji; Nakai, Toshiyuki; Yasuda, Tsuneo [Tetrahedron Letters, 1981, vol. 22, # 24, p. 2291 - 2294]
[2]Lyalin, B. V.; Lozanova, A. V.; Petrosyan, V. A.; Moiseenkov, A. M. [Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1989, vol. 38, # 2, p. 309 - 313][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1989, vol. 38, # 2, p. 361 - 365]
[3]Moiseenkov, A. M.; Lozanova, A. V. [Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1986, vol. 35, # 11, p. 2400 - 2402][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1986, # 11, p. 2615 - 2617]
[4]Lyalin, B. V.; Lozanova, A. V.; Petrosyan, V. A.; Moiseenkov, A. M. [Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1989, vol. 38, # 2, p. 309 - 313][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1989, vol. 38, # 2, p. 361 - 365]
[5]Hegde, Shridhar G.; Vogel, Martin K.; Saddler, John; Hrinyo, Tanya; Rockwell, Ned; et al. [Tetrahedron Letters, 1980, vol. 21, p. 441 - 444]
[6]Moiseenkov, A. M.; Dragan, V. A.; Veselovskii, V. V. [Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1989, vol. 38, # 2, p. 314 - 319][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1989, vol. 38, # 2, p. 365 - 372]

20
[ 150-84-5 ]
[ 74514-34-4 ]
[ 122571-72-6 ]

Yield	Reaction Conditions	Operation in experiment
82%	With pyridine; sulfuryl dichloride In dichloromethane at -60℃;

Reference： [1]Veselovskii, V. V.; Dragan, V. A.; Gafurov, N. M.; Adekenov, S. M.; Kagarlitskii, A. D.; et al. [Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1988, vol. 37, # 10, p. 2185 - 2186][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1988, # 10, p. 2423 - 2424]

21
[ 150-84-5 ]
[ 74514-34-4 ]
E/Z-1-acetoxy-8-chloro-3,7-dimethyl-6-octene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With selenium oxychloride In dichloromethane at -20℃; for 0.75h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

Reference： [1]Moiseenkov, A. M.; Lozanova, A. V. [Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1986, vol. 35, # 11, p. 2400 - 2402][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1986, # 11, p. 2615 - 2617]

22
[ 150-84-5 ]
(3S)-3,7-dimethyl-6,7-epoxyoctan-1-yl acetate [ No CAS ]
[ 1147880-35-0 ]

Yield	Reaction Conditions	Operation in experiment
	With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0℃; for 2h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

Reference： [1]Lee, Eun; Lee, Yong Rok; Moon, Bongjin; Kwon, Ohyun; Shim, Mi Seong; Yun, Jae Sook [Journal of Organic Chemistry, 1994, vol. 59, # 6, p. 1444 - 1456]

23
[ 150-84-5 ]
(3RS,6RS)-6,7-Epoxycitronellyl Acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With 3-chloro-benzenecarboperoxoic acid In chloroform 1.) 0 deg C, 2.) 24 h, room temp.;

Reference： [1]Anderson, Richard J.; Adams, Karen G.; Chinn, Henry R.; Henrick, Clive A. [Journal of Organic Chemistry, 1980, vol. 45, # 11, p. 2229 - 2236]

24
[ 150-84-5 ]
[ 91464-78-7 ]

Yield	Reaction Conditions	Operation in experiment
80%	With diphenyl diselenide; water; magnesium sulfate In acetonitrile at 66 - 68℃; electrolysis under a constant current 6.7 mA/cm²;

Reference： [1]Torii, Sigeru; Uneyama, Kenji; Ono, Michio; Bannou, Tadashi [Journal of the American Chemical Society, 1981, vol. 103, # 15, p. 4606 - 4608]

25
[ 150-84-5 ]
[ 95576-02-6 ]

Yield	Reaction Conditions	Operation in experiment
53%	Stage #1: citronellyl-acetate With tert.-butylhydroperoxide; selenium(IV) oxide In dichloromethane Stage #2: With sodium tetrahydroborate
	With tert.-butylhydroperoxide; sodium tetrahydroborate; selenium(IV) oxide 1.) CH₂Cl₂, 22 deg C, 2.) MeOH; Yield given. Multistep reaction;

Reference： [1]Shibata, Chie; Furukawa, Ayako; Mori, Kenji [Bioscience, Biotechnology and Biochemistry, 2002, vol. 66, # 3, p. 582 - 587]
[2]Williams, David R,; Bremmer, Martin L.; Brown, David L.; D'Antuono, Joseph [Journal of Organic Chemistry, 1985, vol. 50, # 15, p. 2807 - 2809]

26
[ 150-84-5 ]
[ 67-68-5 ]
[ 407-25-0 ]
(6-acetoxy-1-isopropenyl-4-methylhexyl)dimethylsulfonium perchlorate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With lithium perchlorate In dichloromethane at 0℃;

Reference： [1]Moiseenkov, A. M.; Dragan, V. A.; Veselovskii, V. V. [Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1989, vol. 38, # 2, p. 314 - 319][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1989, vol. 38, # 2, p. 365 - 372]

27
[ 150-84-5 ]
[ 67-68-5 ]
[ 407-25-0 ]
[ 123564-19-2 ]

Yield	Reaction Conditions	Operation in experiment
95%	In dichloromethane at 0℃;

28
[ 109143-32-0 ]
[ 150-84-5 ]

Yield	Reaction Conditions	Operation in experiment
90%	With thionyl chloride; triethylamine In dichloromethane at 25℃;

Reference： [1]Grigor'eva, N. Ya.; Lozanova, A. V.; Lutsenko, A. I.; Moiseenkov, A. M. [Bulletin of the Academy of Sciences of the USSR Division of Chemical Science, 1986, vol. 35, # 11, p. 2300 - 2306][Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1986, # 11, p. 2514 - 2520]

29
[ 150-84-5 ]
2,6-Dimethyl-non-2-en-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46 % Chromat.	With tert.-butylhydroperoxide; cetyltrimethylammonium chlorochromate In benzene at 80℃; for 2h;

Reference： [1]Agarwal, D. D.; Kaul, Anju; Raina, Daisy [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1995, vol. 34, # 2, p. 158 - 160]

30
[ 150-84-5 ]
[ 79763-09-0 ]

Yield	Reaction Conditions	Operation in experiment
85%	With tert.-butylhydroperoxide; selenium(IV) oxide; silica gel In dichloromethane for 0.166667h; Irradiation;
60%	With tert.-butylhydroperoxide In dichloromethane; water at 20℃; for 24h;	(E)-3,7-Dimethyl-8-oxooct-6-enyl acetate (4) To a stirred suspension of 5 wt% SeO2 on silica (15.0 g, 6.75 mmol) in CH2Cl2 (135 mL) was added aq 70 wt% tBuOOH (4.9 mL, 34.1 mmol) as a bolus followed by a solution of citronellyl acetate (3.0 mL, 2.7 g, 13.5 mmol) in CH2Cl2 (12.5 mL) added over a period of 15 min. The resulting suspension was stirred vigorously open to the atmosphere for 24 h, and then filtered through a frit. The filtrate was concentrated in vacuo to yield a yellow oil (3.58 g), which was purified by Kugelrohr distillation (130 °C oven temperature/2 Torr) to afford aldehyde 4 (2.86 g, 60%) as a pale yellow oil comprised of a 96:4 mixture of E-and Z-isomers. The E-isomer can be isolated using column chromatography (30% Et2O/hexane) to give analytically pure material with spectroscopic data identical to those reported in the literature.
	With tert.-butylhydroperoxide; selenium(IV) oxide In toluene for 120h; Ambient temperature;

Reference： [1]Singh, Jasvinder; Sharma, Munisha; Kad, Govesdhan L.; Chhabra, Balder R. [Journal of Chemical Research - Part S, 1997, # 7, p. 264 - 265]
[2]Ungarean, Chad N.; Mason, Jeremy D.; Eyer, Benjamin R.; Duca, Nicholas S.; Mong, Jaimie M.; Murphree, S. Shaun [Synthesis, 2017, vol. 49, # 10, p. 2177 - 2181]
[3]Dawson, Glenn W.; Pickett, John A.; Smiley, Diane W. M. [Bioorganic and Medicinal Chemistry, 1996, vol. 4, # 3, p. 351 - 361]

31
[ 106-22-9 ]
[ 108-24-7 ]
[ 150-84-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	With pyridine In dichloromethane at 20℃;
99%	With C₁₂H₈N₂*2CH₄O₃S at 60℃; for 3h;
98%	With iodine at 25℃; for 0.0166667h;

96%	With silica-supported phosphomolybdic acid at 20℃; for 0.133333h;
95%	With lanthanum(III) nitrate at 20℃; for 0.166667h;
95%	With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 16h;	44 PREPARATION 44: 3,7-dimethyloct-6-en-1-yl acetate To a solution of 3,7-dimethyloct-6-en-1-ol (10 g, 63.99 mmol) in DCM (100 mL) were added DIPEA (24.81 g, 191.98 mmol, 33.44 mL) and Ac2O (7.19 g, 70.39 mmol, 6.59 mL). The mixture was stirred at 20°C for 16 hours. TLC (petroleum ether/EtOAc = 10:1, Rf =0.79) indicated the starting material was consumed and one major new spot with lower polarity was detected. The reaction mixture was concentrated under reduced pressure and purified by column chromatography (SiO2) using a gradient of petroleum ether/EtOAc (1:0 to 100:1) to give the title compound as a colorless oil (12 g, 95%).1H NMR (CDCl3) δ ppm 5.06 - 5.10 (m, 1H), 4.06 - 4.13 (m, 2H), 2.03 (s, 3H), 1.68 - 1.95 (m, 2H), 1.64 - 1.65 (m, 1H), 1.53 - 1.60 (m, 4H), 1.44 - 1.45 (m, 3H), 1.34 - 1.42 (m, 1H), 1.17 - 1.19 (m, 2H), 0.92 - 1.17 (d, 1H), 0.90 (d, 3H).
95%	With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 16h;	44 PREPARATION 44: 3,7-dimethyloct-6-en-1-yl acetate To a solution of 3,7-dimethyloct-6-en-1-ol (10 g, 63.99 mmol) in DCM (100 mL) were added DIPEA (24.81 g, 191.98 mmol, 33.44 mL) and Ac2O (7.19 g, 70.39 mmol, 6.59 mL). The mixture was stirred at 20°C for 16 hours. TLC (petroleum ether/EtOAc = 10:1, Rf =0.79) indicated the starting material was consumed and one major new spot with lower polarity was detected. The reaction mixture was concentrated under reduced pressure and purified by column chromatography (SiO2) using a gradient of petroleum ether/EtOAc (1:0 to 100:1) to give the title compound as a colorless oil (12 g, 95%).1H NMR (CDCl3) δ ppm 5.06 - 5.10 (m, 1H), 4.06 - 4.13 (m, 2H), 2.03 (s, 3H), 1.68 - 1.95 (m, 2H), 1.64 - 1.65 (m, 1H), 1.53 - 1.60 (m, 4H), 1.44 - 1.45 (m, 3H), 1.34 - 1.42 (m, 1H), 1.17 - 1.19 (m, 2H), 0.92 - 1.17 (d, 1H), 0.90 (d, 3H).
92%	With nickel dichloride at 20℃; for 0.416667h; Neat (no solvent);
92%	In pyridine at 0 - 30℃; for 12h;
90%	at 20℃; for 6h;
62%	With nickel dichloride for 0.133333h; microwave irradiation;
	With pyridine; dmap
	With pyridine
	With triethylamine In dichloromethane at 20℃; for 16h;
	With immobilized enzyme Novozym 435<SUP>®</SUP> at 150℃; Enzymatic reaction;
93.1 %Spectr.	With sulfonated biochar at 20.1℃; for 4h;

Reference： [1]Shibata, Chie; Furukawa, Ayako; Mori, Kenji [Bioscience, Biotechnology and Biochemistry, 2002, vol. 66, # 3, p. 582 - 587]
[2]Chen, Yongle; Ding, Shiya; Zheng, Wentao; Zhang, Yiyang; Wu, Youting; Hu, Xingbang [Cuihua Xuebao/Chinese Journal of Catalysis, 2016, vol. 37, # 12, p. 2114 - 2121]
[3]Phukan, Prodeep [Tetrahedron Letters, 2004, vol. 45, # 24, p. 4785 - 4787]
[4]Das, Biswanath; Thirupathi, Ponnaboina; Kumar, Rathod Aravind; Laxminarayana, Keetha [Advanced Synthesis and Catalysis, 2007, vol. 349, # 17-18, p. 2677 - 2683]
[5]Reddy, T. Srikanth; Narasimhulu; Suryakiran; Mahesh, K. Chinni; Ashalatha; Venkateswarlu [Tetrahedron Letters, 2006, vol. 47, # 38, p. 6825 - 6829]
[6]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - WO2021/225968, 2021, A1 Location in patent: Paragraph 0219; 0220
[7]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - WO2021/225968, 2021, A1 Location in patent: Paragraph 0219; 0220
[8]Location in patent: experimental part Meshram, Gangadhar; Patil, Vishvanath D. [Synthetic Communications, 2009, vol. 39, # 24, p. 4384 - 4395]
[9]Buntasana, Supanat; Hayashi, Jun; Klumphu, Piyatida; Padungros, Panuwat; Saetung, Prakorn; Vilaivan, Tirayut [Journal of Organic Chemistry, 2021]
[10]Chakraborti, Asit K.; Gulhane, Rajesh [Tetrahedron Letters, 2003, vol. 44, # 17, p. 3521 - 3525]
[11]Constantinou-Kokotou, Violetta; Peristeraki, Anna [Synthetic Communications, 2004, vol. 34, # 22, p. 4227 - 4232]
[12]Dawson, Glenn W.; Pickett, John A.; Smiley, Diane W. M. [Bioorganic and Medicinal Chemistry, 1996, vol. 4, # 3, p. 351 - 361]
[13]Garcia-Rubio, Silvina; Attygalle, Athula B; Weldon, Paul J; Meinwald, Jerrold [Journal of chemical ecology, 2002, vol. 28, # 4, p. 769 - 781]
[14]Ortar, Giorgio; Schiano Moriello, Aniello; Morera, Enrico; Nalli, Marianna; Di Marzo, Vincenzo; De Petrocellis, Luciano [Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 23, p. 5507 - 5511]
[15]Adarme, Carlos A.A.; Leão, Raquel A.C.; de Souza, Stefania P.; Itabaiana, Ivaldo; de Souza, Rodrigo O.M.A.; Rezende, Claudia M. [Molecular catalysis, 2018, vol. 453, p. 39 - 46]
[16]Kerton, Francesca M.; MacQuarrie, Stephanie L.; Vidal, Juliana L.; Wyper, Olivia M. [European Journal of Organic Chemistry, 2021, vol. 2021, # 44, p. 6052 - 6056]

32
[ 106-22-9 ]
[ 141-78-6 ]
[ 150-84-5 ]

Yield	Reaction Conditions	Operation in experiment
	With Mucor miehei lipase at 55 - 60℃; for 8h;
100 %Spectr.	With Candida rugosa lipase In toluene at 40℃; for 96h; Enzymatic reaction;
	With immobilized enzyme Novozym 435<SUP>®</SUP> at 50℃; for 0.133333h; Enzymatic reaction;

Reference： [1]Chatterjee; Bhattacharyya [Journal of the American Oil Chemists' Society, 1998, vol. 75, # 5, p. 651 - 655]
[2]Ramilijaona, Jade; Raynaud, Elsa; Bouhlel, Charfeddine; Sarrazin, Elise; Fernandez, Xavier; Antoniotti, Sylvain [Chemistry and biodiversity, 2013, vol. 10, # 12, p. 2291 - 2301]
[3]Adarme, Carlos A.A.; Leão, Raquel A.C.; de Souza, Stefania P.; Itabaiana, Ivaldo; de Souza, Rodrigo O.M.A.; Rezende, Claudia M. [Molecular catalysis, 2018, vol. 453, p. 39 - 46]

33
[ 150-84-5 ]
[ 74-95-3 ]
6-acetoxy-4-methyl-2-methylenehexanal [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	Stage #1: citronellyl-acetate With ozone In dichloromethane at -78℃; Stage #2: 1,1-dibromomethane With diethylamine In dichloromethane at -78 - 55℃;

Reference： [1]Hon, Yung-Son; Chang, Feng-Jon; Lu, Ling; Lin, Wei-Chi [Tetrahedron, 1998, vol. 54, # 20, p. 5233 - 5246]

34
[ 106-22-9 ]
[ 64-19-7 ]
[ 150-84-5 ]

Yield	Reaction Conditions	Operation in experiment
99.9%	With Candida antarctica lipase B at 50℃; for 4h; Molecular sieve; Ionic liquid; Green chemistry; Enzymatic reaction;
95%	With ZrCl₄-Mg(ClO₄)₂ composite In neat (no solvent) at 20℃; for 0.133333h;	Typical experimental procedure for the onepotsynthesis of benzyl acetate General procedure: A mixture of 4-methoxy benzyl alcohol (1b, 1 mmol),acetic acid (3 mmol), 2 mol% ZrCl4-Mg(ClO4)2 catalyst was stirred at room temperature for the time specified inTable 5. After completion of reaction (monitored by TLC),the solid or liquid product was filtered and washed with25 ml diethyl ether and water. The organic layer wassuccessively washed with saturated NaHCO3 solution. Theorganic layer was dried over anhydrous sodium sulfateand evaporated of the solvent under reduced pressure toprovide a residue which was passed through a short padof silica gel (60-120 mesh) using hexane as eluent to providethe analytically pure acylated product (please seeAppendix S1).Note that as we know that esterification is a reversiblereaction, to avoid this reversible we used every time activatedmolecular sieves as dehydrating agent/waterabsorbing agent. We have not mentioned it in our actualexperimental procedure.
90%	With cetyltrimethylammonium chloride; potassium hexacyanoferrate(III) at 80℃; for 1h;

	With molecular sieve at 120℃; for 8h;
	With tin(II) chloride dihdyrate In acetonitrile at 24.84℃; for 6h;
	With N,N′,N′′,N′′′-hexadecyltrimethylammonium bis(trifluoromethylsulfonyl)imide; Novozym 435 (immobilized Candida antarctica lipase B) at 50℃; for 4h; Green chemistry; Enzymatic reaction;	Lipase-catalyzed synthesis of flavour esters in sponge-like ionic liquid (SLILs) Three mmol of citronellol, geraniol, nerol or anisyl alcohol, and 1, 2 or 3mmol of acetic acid were added to 3mL screw-capped vials with teflon-lined septa. Then, the corresponding amount of [C16tma][NTf2] was added to reach a final IL concentration of 60 or 70% (w/w) with respect to the mass substrates. Reaction mixtures were pre-incubated at 50°C for 10min, resulting in fully clear monophasic systems. Then, 80mg of MS13× per mmol of carboxylic acid were also added. The reaction was started by adding Novozym 435 (40mg/mmol of carboxylic acid) and the reaction was incubated for 4h at 50°C while shaking (300rpm), or under 4W microwave irradiation (which provided a 50°C constant temperature). For products analysis, aliquots (20μL) were taken at selected times and suspended in 500μL octane, and the resulting biphasic mixture was shaken to extract the products. The resulting mixture was centrifuged at 14,000rpm for 10min. Finally, 300μL of the octane extract were added to 100μL of a 100mM ethyl propionate (internal standard) solution in octane, and the final solution was analyzed by CG. For full recovery of the flavour ester products at 4h, the reaction mixtures were consecutively centrifuged four times at 14,000rpm (15min) and at room temperature, 21, 10 and 4°C, which resulted in a top liquid phase of flavour ester and a bottom solid phase containing the SLIL. For the case of anisyl acetate, the reaction mixture was cooled in an ice bath for 3h, and the resulting solid mixture was placed in a centrifugal filter, then centrifuged at 16,000rpm (10min) and at 0°C. This resulted in a top SLIL solid phase, which was retained inside the filter, and a bottom liquid phase of anisyl acetate. For all cases, a sample (10μL) of the resulting flavour ester phase was dissolved in 1mL acetone-δ6, then analyzed by 300MHz 1H NMR and 282MHz 19F NMR, in a Brucker AC 300E spectrometer for SLIL detection. All experiments were carried out in duplicate.
	With Iron(III) nitrate nonahydrate In acetonitrile at 64.84℃; for 3h;

Reference： [1]Lozano, Pedro; Bernal, Juana M.; Navarro, Alicia [Green Chemistry, 2012, vol. 14, # 11, p. 3026 - 3033]
[2]Alam, Mohammad Mujahid; Atkore, Sandeep T.; Kamble, Vinod T.; Varala, Ravi [Bulletin of the Korean Chemical Society, 2022, vol. 43, # 4, p. 570 - 576]
[3]Location in patent: experimental part Dewan, Anindita; Bora, Utpal; Kakati, Dilip Kumar [Bulletin of the Korean Chemical Society, 2010, vol. 31, # 12, p. 3870 - 3871]
[4]Waghmode, Suresh B.; Thakur, Vinay V.; Sudalai, Arumugam; Sivasanker, Subramanian [Tetrahedron Letters, 2001, vol. 42, # 17, p. 3145 - 3147]
[5]Da Silva; Julio; Dos Santos [Catalysis science and technology, 2015, vol. 5, # 2, p. 1261 - 1266]
[6]Lozano, Pedro; Bernal, Juana M.; Gómez, Celia; García-Verdugo, Eduardo; Isabel Burguete; Sánchez, Gregorio; Vaultier, Michel; Luis, Santiago V. [Catalysis Today, 2015, vol. 255, p. 54 - 59]
[7]Da Silva; Ayala [Catalysis science and technology, 2016, vol. 6, # 9, p. 3197 - 3207]

35
[ 106-22-9 ]
[ 75-36-5 ]
[ 150-84-5 ]

Yield	Reaction Conditions	Operation in experiment
98%	With potassium fluoride on basic alumina In toluene for 1h;

Reference： [1]Yadav, Veejendra K; Ganesh Babu; Mittal, Manish [Tetrahedron, 2001, vol. 57, # 32, p. 7047 - 7051]

36
[ 150-84-5 ]
[ 69226-51-3 ]
acetic acid 5-[3,3-dimethyl-1-(2,2,2-trichloro-ethoxysulfonyl)-aziridin-2-yl]-3-methyl-pentyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	Stage #1: citronellyl-acetate; 2,2,2-trichloroethyl sulfamate With tetra(trifluoroacetamidato)dirhodium(II); magnesium oxide In benzene at 0℃; Stage #2: With [bis(acetoxy)iodo]benzene In benzene at 0 - 25℃; for 8h; Further stages.;

Reference： [1]Guthikonda, Kiran; Bois, J. Du [Journal of the American Chemical Society, 2002, vol. 124, # 46, p. 13672 - 13673]

37
[ 150-84-5 ]
[ 96740-50-0 ]

Yield	Reaction Conditions	Operation in experiment
85%	With selenium(IV) oxide; urea-hydrogen peroxide In water; isopropyl alcohol for 0.0111111h; microwave irradiation;

Reference： [1]Manktala; Dhillon; Chhabra [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 6, p. 1591 - 1594]

38
[ 150-84-5 ]
[ 70-55-3 ]
N-(1,1,5-trimethyl-7-acetoxyheptyl)-4-toluenesulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%	With (triphenylphosphine)gold(I) chloride; silver trifluoromethanesulfonate In toluene at 85℃; for 48h;

Reference： [1]Zhang, Junliang; Yang, Cai-Guang; He, Chuan [Journal of the American Chemical Society, 2006, vol. 128, # 6, p. 1798 - 1799]

39
[ 150-84-5 ]
[ 86414-50-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: SeO₂; tBuOOH / CH₂Cl₂ 1.2: 53 percent / NaBH₄ 2.1: 95 percent / pyridine / CH₂Cl₂ / 5 h / 20 °C 3.1: 63 percent / Li₂CuCl₄ / tetrahydrofuran / 3.5 h / -78 - 4 °C 4.1: 87 percent / H₂ / 10 percent Pd/C / ethanol / 24 h / 20 °C

Reference： [1]Shibata, Chie; Furukawa, Ayako; Mori, Kenji [Bioscience, Biotechnology and Biochemistry, 2002, vol. 66, # 3, p. 582 - 587]

40
[ 150-84-5 ]
(+/-)-3,7,11,15-tetramethylhentriacontane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1.1: SeO₂; tBuOOH / CH₂Cl₂ 1.2: 53 percent / NaBH₄ 2.1: 95 percent / pyridine / CH₂Cl₂ / 5 h / 20 °C 3.1: 63 percent / Li₂CuCl₄ / tetrahydrofuran / 3.5 h / -78 - 4 °C 4.1: 87 percent / H₂ / 10 percent Pd/C / ethanol / 24 h / 20 °C 5.1: pyridine / CH₂Cl₂ / 17 h / 4 °C 6.1: 3.33 g / NaI / dimethylformamide / 2 h / 50 °C 7.1: 99 percent / n-butyllithium; HMPA / tetrahydrofuran; hexane / -78 - 0 °C 8.1: 83 percent / lithium; EtNH₂ / tetrahydrofuran / 2 h / -60 - -50 °C

Reference： [1]Shibata, Chie; Furukawa, Ayako; Mori, Kenji [Bioscience, Biotechnology and Biochemistry, 2002, vol. 66, # 3, p. 582 - 587]

41
[ 150-84-5 ]
[ 190332-49-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: SeO₂; tBuOOH / CH₂Cl₂ 1.2: 53 percent / NaBH₄ 2.1: 95 percent / pyridine / CH₂Cl₂ / 5 h / 20 °C 3.1: 70 percent / Li₂CuCl₄ / tetrahydrofuran / 3.5 h / -78 - 4 °C 4.1: 90 percent / H₂ / 10 percent Pd/C / ethanol / 24 h / 20 °C

Reference： [1]Shibata, Chie; Furukawa, Ayako; Mori, Kenji [Bioscience, Biotechnology and Biochemistry, 2002, vol. 66, # 3, p. 582 - 587]

42
[ 150-84-5 ]
[ 441296-73-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: SeO₂; tBuOOH / CH₂Cl₂ 1.2: 53 percent / NaBH₄ 2.1: 95 percent / pyridine / CH₂Cl₂ / 5 h / 20 °C 3.1: 63 percent / Li₂CuCl₄ / tetrahydrofuran / 3.5 h / -78 - 4 °C 4.1: 87 percent / H₂ / 10 percent Pd/C / ethanol / 24 h / 20 °C 5.1: pyridine / CH₂Cl₂ / 17 h / 4 °C 6.1: 3.33 g / NaI / dimethylformamide / 2 h / 50 °C

Reference： [1]Shibata, Chie; Furukawa, Ayako; Mori, Kenji [Bioscience, Biotechnology and Biochemistry, 2002, vol. 66, # 3, p. 582 - 587]

43
[ 150-84-5 ]
[ 441296-76-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: SeO₂; tBuOOH / CH₂Cl₂ 1.2: 53 percent / NaBH₄ 2.1: 95 percent / pyridine / CH₂Cl₂ / 5 h / 20 °C 3.1: 70 percent / Li₂CuCl₄ / tetrahydrofuran / 3.5 h / -78 - 4 °C 4.1: 90 percent / H₂ / 10 percent Pd/C / ethanol / 24 h / 20 °C 5.1: pyridine / CH₂Cl₂ / 17 h / 4 °C 6.1: 1.80 g / NaI / dimethylformamide / 2 h / 50 °C

Reference： [1]Shibata, Chie; Furukawa, Ayako; Mori, Kenji [Bioscience, Biotechnology and Biochemistry, 2002, vol. 66, # 3, p. 582 - 587]

44
[ 150-84-5 ]
[ 441296-72-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: SeO₂; tBuOOH / CH₂Cl₂ 1.2: 53 percent / NaBH₄ 2.1: 95 percent / pyridine / CH₂Cl₂ / 5 h / 20 °C 3.1: 63 percent / Li₂CuCl₄ / tetrahydrofuran / 3.5 h / -78 - 4 °C 4.1: 87 percent / H₂ / 10 percent Pd/C / ethanol / 24 h / 20 °C 5.1: pyridine / CH₂Cl₂ / 17 h / 4 °C

Reference： [1]Shibata, Chie; Furukawa, Ayako; Mori, Kenji [Bioscience, Biotechnology and Biochemistry, 2002, vol. 66, # 3, p. 582 - 587]

45
[ 150-84-5 ]
[ 441296-75-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: SeO₂; tBuOOH / CH₂Cl₂ 1.2: 53 percent / NaBH₄ 2.1: 95 percent / pyridine / CH₂Cl₂ / 5 h / 20 °C 3.1: 70 percent / Li₂CuCl₄ / tetrahydrofuran / 3.5 h / -78 - 4 °C 4.1: 90 percent / H₂ / 10 percent Pd/C / ethanol / 24 h / 20 °C 5.1: pyridine / CH₂Cl₂ / 17 h / 4 °C

Reference： [1]Shibata, Chie; Furukawa, Ayako; Mori, Kenji [Bioscience, Biotechnology and Biochemistry, 2002, vol. 66, # 3, p. 582 - 587]

46
[ 150-84-5 ]
(+/-)-4,8,12,16-tetramethyldotriacontane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1.1: SeO₂; tBuOOH / CH₂Cl₂ 1.2: 53 percent / NaBH₄ 2.1: 95 percent / pyridine / CH₂Cl₂ / 5 h / 20 °C 3.1: 70 percent / Li₂CuCl₄ / tetrahydrofuran / 3.5 h / -78 - 4 °C 4.1: 90 percent / H₂ / 10 percent Pd/C / ethanol / 24 h / 20 °C 5.1: pyridine / CH₂Cl₂ / 17 h / 4 °C 6.1: 1.80 g / NaI / dimethylformamide / 2 h / 50 °C 7.1: 85 percent / n-butyllithium; HMPA / tetrahydrofuran; hexane / -78 - 0 °C 8.1: 81 percent / lithium; EtNH₂ / tetrahydrofuran / 2 h / -60 - -50 °C

Reference： [1]Shibata, Chie; Furukawa, Ayako; Mori, Kenji [Bioscience, Biotechnology and Biochemistry, 2002, vol. 66, # 3, p. 582 - 587]

47
[ 150-84-5 ]
[ 441296-83-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1.1: SeO₂; tBuOOH / CH₂Cl₂ 1.2: 53 percent / NaBH₄ 2.1: 95 percent / pyridine / CH₂Cl₂ / 5 h / 20 °C 3.1: 63 percent / Li₂CuCl₄ / tetrahydrofuran / 3.5 h / -78 - 4 °C 4.1: 87 percent / H₂ / 10 percent Pd/C / ethanol / 24 h / 20 °C 5.1: pyridine / CH₂Cl₂ / 17 h / 4 °C 6.1: 3.33 g / NaI / dimethylformamide / 2 h / 50 °C 7.1: 99 percent / n-butyllithium; HMPA / tetrahydrofuran; hexane / -78 - 0 °C

Reference： [1]Shibata, Chie; Furukawa, Ayako; Mori, Kenji [Bioscience, Biotechnology and Biochemistry, 2002, vol. 66, # 3, p. 582 - 587]

48
[ 150-84-5 ]
[ 441296-84-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1.1: SeO₂; tBuOOH / CH₂Cl₂ 1.2: 53 percent / NaBH₄ 2.1: 95 percent / pyridine / CH₂Cl₂ / 5 h / 20 °C 3.1: 70 percent / Li₂CuCl₄ / tetrahydrofuran / 3.5 h / -78 - 4 °C 4.1: 90 percent / H₂ / 10 percent Pd/C / ethanol / 24 h / 20 °C 5.1: pyridine / CH₂Cl₂ / 17 h / 4 °C 6.1: 1.80 g / NaI / dimethylformamide / 2 h / 50 °C 7.1: 85 percent / n-butyllithium; HMPA / tetrahydrofuran; hexane / -78 - 0 °C

Reference： [1]Shibata, Chie; Furukawa, Ayako; Mori, Kenji [Bioscience, Biotechnology and Biochemistry, 2002, vol. 66, # 3, p. 582 - 587]

49
[ 150-84-5 ]
[ 26489-18-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: SeO₂, t-BuOOH / toluene / 120 h / Ambient temperature 2: LiAlH₄ / diethyl ether / 1 h

Reference： [1]Dawson, Glenn W.; Pickett, John A.; Smiley, Diane W. M. [Bioorganic and Medicinal Chemistry, 1996, vol. 4, # 3, p. 351 - 361]

50
[ 150-84-5 ]
[ 194092-52-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: SeO₂, t-BuOOH / toluene / 120 h / Ambient temperature 2: 81 percent / aq. K₂CO₃ / methanol / 1 h

Reference： [1]Dawson, Glenn W.; Pickett, John A.; Smiley, Diane W. M. [Bioorganic and Medicinal Chemistry, 1996, vol. 4, # 3, p. 351 - 361]

51
[ 150-84-5 ]
(+/-)-<10-3H>-10-hydroxycitronellol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: SeO₂, t-BuOOH / toluene / 120 h / Ambient temperature 2: NaBT₄ / ethanol / 1 h 3: aq. K₂CO₃ / methanol / 1 h

Reference： [1]Dawson, Glenn W.; Pickett, John A.; Smiley, Diane W. M. [Bioorganic and Medicinal Chemistry, 1996, vol. 4, # 3, p. 351 - 361]

52
[ 150-84-5 ]
(E)-2,6-dimethyloct-2-enedial [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: SeO₂, t-BuOOH / toluene / 120 h / Ambient temperature 2: LiAlH₄ / diethyl ether / 1 h 3: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 10 min, 2.) CH₂Cl₂, from -78 deg C to RT

Reference： [1]Dawson, Glenn W.; Pickett, John A.; Smiley, Diane W. M. [Bioorganic and Medicinal Chemistry, 1996, vol. 4, # 3, p. 351 - 361]

53
[ 150-84-5 ]
C₁₂H₂₁⁽³⁾HO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: SeO₂, t-BuOOH / toluene / 120 h / Ambient temperature 2: NaBT₄ / ethanol / 1 h

Reference： [1]Dawson, Glenn W.; Pickett, John A.; Smiley, Diane W. M. [Bioorganic and Medicinal Chemistry, 1996, vol. 4, # 3, p. 351 - 361]

54
[ 150-84-5 ]
[ 97012-68-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1: 1.) SeO₂, t-BuOOH, 2.) NaBH₄ / 1.) CH₂Cl₂, 22 deg C, 2.) MeOH 2: 95 percent / imidazole / dimethylformamide / 0 °C 3: 95 percent / LiOH / methanol / 22 °C 4: 85 percent / PCC / CH₂Cl₂ / 1 h / 22 °C 5: 73 percent / LDA / tetrahydrofuran / 2 h / -78 - 20 °C 6: 89 percent / Dibal / CH₂Cl₂ / 0.17 h / -78 °C 7: LiH, SO₃, pyridine / 2 h / 22 °C 8: LiAlH₄ / 16 h / 22 °C 9: 96 percent / n-Bu₄N(+)F(-) / tetrahydrofuran / 22 °C 10: 82 percent / PCC / CH₂Cl₂ / 1 h / 22 °C