[ CAS No. 1647-16-1 ] {[proInfo.proName]}

Name: 1647-16-1|Deca-1,9-diene|98%
Brand: Ambeed
SKU: A515748
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Quality Control of [ 1647-16-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1647-16-1 ]

SDS Specification

Alternatived Products of [ 1647-16-1 ]

Product Details of [ 1647-16-1 ]

CAS No. :	1647-16-1	MDL No. :	MFCD00008670
Formula :	C₁₀H₁₈	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NLDGJRWPPOSWLC-UHFFFAOYSA-N
M.W :	138.25	Pubchem ID :	15439
Synonyms :

Calculated chemistry of [ 1647-16-1 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.6
Num. rotatable bonds :	7
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	49.24
TPSA :	0.0 Å²

Pharmacokinetics

GI absorption :	Low
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) :	-3.49 cm/s

Lipophilicity

Log Po/w (iLOGP) :	3.04
Log Po/w (XLOGP3) :	5.14
Log Po/w (WLOGP) :	3.7
Log Po/w (MLOGP) :	3.66
Log Po/w (SILICOS-IT) :	3.54
Consensus Log Po/w :	3.81

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	3.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.47
Solubility :	0.0465 mg/ml ; 0.000336 mol/l
Class :	Soluble
Log S (Ali) :	-4.88
Solubility :	0.0018 mg/ml ; 0.000013 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-3.17
Solubility :	0.093 mg/ml ; 0.000673 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	1.89

Safety of [ 1647-16-1 ]

Signal Word:	Danger	Class:	3
Precautionary Statements:	P261-P273-P305+P351+P338	UN#:	3295
Hazard Statements:	H225-H315-H319-H335-H400	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 1647-16-1 ]

* 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.

Upstream synthesis route of [ 1647-16-1 ]
Downstream synthetic route of [ 1647-16-1 ]

[ 1647-16-1 ] Synthesis Path-Upstream 1~3

1
[ 1647-16-1 ]
[ 4101-68-2 ]

Yield	Reaction Conditions	Operation in experiment
58 mol %	With HBr gas; sodium hydrogencarbonate; dibenzoyl peroxide In diethyl ether; hexane; water	EXAMPLE II A 5 liter, 3-necked flask was equipped with a mechanical stirrer, a fritted bubbler and a gas outlet adapter. A solution of 1,9-decadiene (500 g, 3.6 mol) and 5 g of benzoyl peroxide in 1 L of n-hexane was placed in the flask, which was chilled to about 5° C. and maintained at 5°-10° C. while HBr gas was bubbled through. HBr gas was introduced over a 7 hour period, at which time the reaction mixture was poured into about 2 L of water, then neutralized by addition of NaHCO₃. About 200 mL of diethyl ether was added, the solution thoroughly mixed, then allowed to stand overnight. After settling, the aqueous layer was separated and extracted with about 200 mL of ether. The organic layers were then combined, dried over MgSO₄, filtered, and stripped of solvent on a rotary evaporator. Distillation of the crude product through a two foot packed glass column gave about 625 g (58 mol percent yield) of 1,10-dibromodecane.

Reference： [1] Synlett, 2010, # 13, p. 2014 - 2018
[2] Patent: US4540826, 1985, A,

2
[ 110-52-1 ]
[ 1730-25-2 ]
[ 1647-16-1 ]
[ 4117-09-3 ]

Reference： [1] Organic Process Research and Development, 2007, vol. 11, # 1, p. 60 - 63

3
[ 110-52-1 ]
[ 106-95-6 ]
[ 1647-16-1 ]
[ 592-42-7 ]
[ 4117-09-3 ]
[ 21964-49-8 ]

Reference： [1] Bulletin de la Societe Chimique de France, 1968, p. 3893 - 3903

[ 1647-16-1 ] Synthesis Path-Downstream 1~10

1
[ 1647-16-1 ]
[ 16538-91-3 ]

Yield	Reaction Conditions	Operation in experiment
75%	With chromium(VI) oxide; palladium dichloride; In water; acetonitrile; at 20 - 60℃; for 14h;	General procedure: To a stirred solution of olefin (0.4mmol) in CH3CN (3.5mL) and H2O (0.5mL) were added PdCl2 (3.6mg, 0.02mmol, 5mol%) and CrO3 (20mg, 0.6mmol, 0.5equiv) at room temperature. The reaction mixture was warmed to 60C and stirred for specified time (see Tables 5-7) in a closed flask. The reaction mixture was then filtered through a small pad of silica gel and washed with EtOAc and the filtrate concentrated. The residue in some cases contained virtually pure compound and no further purification was necessary. In other cases the residue was purified by silica gel column chromatography using petroleum ether/EtOAc as an eluent to afford the methyl ketones.

Reference： [1]Tetrahedron Letters,1983,vol. 24,p. 5159 - 5162
[2]Journal of Organic Chemistry,2016,vol. 81,p. 2113 - 2121
[3]Tetrahedron,2014,vol. 70,p. 4760 - 4767
[4]Tetrahedron Letters,1983,vol. 24,p. 5159 - 5162

2
[ 1647-16-1 ]
[ 16538-91-3 ]
[ 97963-22-9 ]

Reference： [1]Tetrahedron Letters,1985,vol. 26,p. 2263 - 2264

3
[ 1647-16-1 ]
O₂ [ No CAS ]
[ 16538-91-3 ]

Reference： [1]Tetrahedron Letters,1983,vol. 24,p. 5159 - 5162

4
[ 1647-16-1 ]
[ 108-24-7 ]
[ 65423-25-8 ]
[ 821-38-5 ]

Reference： [1]Journal of Organic Chemistry,2003,vol. 68,p. 5974 - 5976

5
[ 110-91-8 ]
[ 1647-16-1 ]
[ 1956-30-5 ]
Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-[5-((E)-1-methyl-9-morpholin-4-yl-non-7-enyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-tetrahydro-furan-3-yl ester [ No CAS ]
Acetic acid (2R,3S,5R)-2-acetoxymethyl-5-[5-((E)-10-morpholin-4-yl-dec-8-enyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-tetrahydro-furan-3-yl ester [ No CAS ]

Reference： [1]Tetrahedron,2005,vol. 61,p. 11427 - 11439

6
[ 1647-16-1 ]
[ 689-12-3 ]
(2E,10E)-Dodeca-2,10-dienedioic acid diisopropyl ester [ No CAS ]

Reference： [1]Chemical Communications,2005,p. 3998 - 4000

7
[ 112-38-9 ]
[ 1647-16-1 ]

Yield	Reaction Conditions	Operation in experiment
85%	With nickel(II) iodide; triphenylphosphine In neat (no solvent) for 16h; Inert atmosphere; Sealed tube;
59%	With bis-triphenylphosphine-palladium(II) chloride; 3,3',5,5'-tetra(tert-butyl)biphenyl-2,2'-diol; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In neat (no solvent) at 132℃; for 3h; Inert atmosphere;
	Stage #1: 10-undecenoic acid With bis(1,5-cyclooctadiene)diiridium(I) dichloride; triphenylphosphine; potassium iodide at 20℃; for 0.5h; Inert atmosphere; Schlenk technique; Stage #2: With acetic anhydride at 160℃; for 5h; Inert atmosphere; Schlenk technique; regioselective reaction;

	With formate dehydrogenase; 1200 U catalase; OleT in combination with the putidaredoxin electron-transfer system CamAB; P₄₅₀ monooxygenase OleT; ammonium formate; β-nicotinamide adenine dinucleotide, disodium salt, reduced form In ethanol Enzymatic reaction;
	Multi-step reaction with 2 steps 1.1: triethylamine / dichloromethane / 0.17 h / Inert atmosphere 1.2: 20 °C / Inert atmosphere 2.1: palladium dichloride; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; lithium chloride; 1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene / 2.5 h / 190 °C / Schlenk technique; Inert atmosphere; Glovebox; Sealed tube
71 %Chromat.	With sodium phosphite; phosphite dehydrogenase; OleT<SUB>JE </SUB>decarboxylase/P₄₅₀BM₃ reductase domain fusion protein; oxygen; NADPH; catalase In water at 20℃; for 12h; Green chemistry; Enzymatic reaction;
	With bis(1,5-cyclooctadiene)diiridium(I) dichloride; N,N-diphenylaminobenzene; acetic anhydride; potassium iodide at 160℃; for 12h; Inert atmosphere; Green chemistry; chemoselective reaction;

Reference： [1]John, Alex; Hillmyer, Marc A.; Tolman, William B. [Organometallics, 2017, vol. 36, # 3, p. 506 - 509]
[2]Liu, Yiyang; Kim, Kelly E.; Herbert, Myles B.; Fedorov, Alexey; Grubbs, Robert H.; Stoltz, Brian M. [Advanced Synthesis and Catalysis, 2014, vol. 356, # 1, p. 130 - 136]
[3]Ternel, Jérémy; Lebarbé, Thomas; Monflier, Eric; Hapiot, Frédéric [ChemSusChem, 2015, vol. 8, # 9, p. 1585 - 1592]
[4]Dennig, Alexander; Kurakin, Sara; Kuhn, Miriam; Dordic, Andela; Hall, Mélanie; Faber, Kurt [European Journal of Organic Chemistry, 2016, vol. 2016, # 21, p. 3473 - 3477]
[5]John, Alex; Dereli, Büsra; OrtunÌo, Manuel A.; Johnson, Hillis E.; Hillmyer, Marc A.; Cramer, Christopher J.; Tolman, William B. [Organometallics, 2017, vol. 36, # 15, p. 2956 - 2964]
[6]Lu, Chen; Shen, Fenglin; Wang, Shuaibo; Wang, Yuyang; Liu, Juan; Bai, Wen-Ju; Wang, Xiqing [ACS Catalysis, 2018, vol. 8, # 7, p. 5794 - 5798]
[7]Ternel, Jérémy; Léger, Bastien; Monflier, Eric; Hapiot, Frédéric [Catalysis science and technology, 2018, vol. 8, # 15, p. 3948 - 3953]

8
[ 112-47-0 ]
[ 1647-16-1 ]
[ 13019-22-2 ]

Yield	Reaction Conditions	Operation in experiment
88%	With 1-hexadecylcarboxylic acid at 340℃; for 6h; Molecular sieve;	1 A process for the synthesis of 9-decenol, comprising the steps of:1), a 500 mL four-necked flask equipped with a thermometer, a 10 cm rectifying column, a stirring blade, and a heatable dropping funnel equipped with a condenser at the top was charged with 120 g (0.69 mol) of 1,10-decanediol, 0.43mol) palmitic acid, the molar ratio of them is 1.6: 1; and 15gZSM-5 molecular sieve is added.The temperature was raised to 340 ° C, and 1,10-decanediol was continuously fed in a dropwise manner to carry out the reaction.Feeding speed 30g / h, adjust the feed rate, so that consistent with the discharge speed.The reaction was continued for 6 hours, feeding 190 g and discharging about 180 g.The remaining mixture in the four-necked flask can continue as a base material for continuous reaction.2), the material will be atmospheric distillation, by-product 1,9-decadiene and water azeotropic distillation, azeotropic point 99 .The remaining anhydrous material vacuum distillation, collecting 110 ° C / 30mmHg fraction, 9-decenol product, yield 88%, purity 99.4%.

Reference： [1]Current Patent Assignee: HANGZHOU KAIMING PANGDE BIOTECHNOLOGY - CN105330516, 2016, A Location in patent: Paragraph 0035 - 0038

9
[ 931-87-3 ]
[ 3195-24-2 ]
[ 1647-16-1 ]
[ 21622-00-4 ]

Yield	Reaction Conditions	Operation in experiment
	With C₃₄H₃₆I₂N₂RuS In ⁽²⁾H₈-toluene at 80℃; for 1h;

Reference： [1]Ivry, Elisa; Lemcoff, N. Gabriel; Nechmad, Noy B.; Phatake, Ravindra; Poater, Albert [Angewandte Chemie - International Edition, 2020, vol. 59, # 9, p. 3539 - 3543][Angew. Chem., 2020, vol. 132, p. 3567 - 3571,5]

10
[ 1647-16-1 ]
[ 112-47-0 ]

Yield	Reaction Conditions	Operation in experiment
91%	Stage #1: 1,10-decadiene With 9-bora-bicyclo[3.3.1]nonane In tetrahydrofuran at 40℃; for 0.0666667h; Stage #2: With dihydrogen peroxide; sodium hydroxide In ethanol; water at 20℃; for 0.0488333h;
69%	Stage #1: 1,10-decadiene With sodium tetrahydroborate; iodine; ethylene dibromide In 1,2-dimethoxyethane at 25℃; for 20h; Stage #2: With dihydrogen peroxide; sodium hydroxide In water at 0 - 25℃; for 0.333333h;	Typical procedure for hydroboration of alkenes with borane from NaBH₄ and I₂ using the PV method (Condition B) General procedure: Iodide (305 mg, 1.2 mmol) and a magnetic stirring bar were placed at the bottom of a test tube (15 mmf × 130 mm), to which 1,2-dibromoethane (0.5 mL) was added slowly to dissolve the iodide. FC-72 (2mL) was added slowly using a syringe. Subsequently, NaBH4 (84 mg, 2.2 mmol), a solution of 4-methylstyrene (1a) (240 mg, 2.0 mmol) in DME (5.0 mL) was added slowly in order, forming four layers. A rubber septum was fitted to the test tube, and a needle equipped with a balloon, which acted asa reservoir of borane gas during the reaction, was then pricked into the septum. The air in the test tube was removed by a syringe until the balloon was completely flattened. The test tube was stirred slowlyfor 20 h at 25 °C, taking care not to mix the layers. The reaction mixture was then cooled to 0 °C withice while stirring. An aqueous NaOH solution (1 M, 1.35 mL) was added slowly in ten portions.Verifying that organic layer was changed to basic condition using a pH test paper, H2O2 solution (30%,0.5 mL) was added slowly in two portion. After 20 min stirring, the organic layer was taken up with aglass pipette to a separating funnel, and washed with water and brine three times. The organic layer was dried over Na2SO4. After filtration, the solvent was evaporated. The residue was then purified by column chromatography on silica gel, eluting hexane/ethyl acetate (8:2) afforded 2-(p-tolyl)-1-ethanol (2a) (172mg, 63%).

Reference： [1]Elsherbini, Mohamed; Huynh, Florence; Dunbabin, Alice; Allemann, Rudolf K.; Wirth, Thomas [Chemistry - A European Journal, 2020, vol. 26, # 50, p. 11423 - 11425]
[2]Soga, Nene; Yoshiki, Tomo; Sato, Aoi; Kawamoto, Takuji; Ryu, Ilhyong; Matsubara, Hiroshi [Tetrahedron Letters, 2021, vol. 69]

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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
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H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 1647-16-1 ] {[proInfo.proName]}

Quality Control of [ 1647-16-1 ]

Related Doc. of [ 1647-16-1 ]

Product Details of [ 1647-16-1 ]

Calculated chemistry of [ 1647-16-1 ]

Physicochemical Properties

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Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1647-16-1 ]

Application In Synthesis of [ 1647-16-1 ]

[ 1647-16-1 ] Synthesis Path-Upstream 1~3

[ 1647-16-1 ] Synthesis Path-Downstream 1~10

Related Functional Groups of [ 1647-16-1 ]

Alkenes

Aliphatic Chain Hydrocarbons

Precautionary Statements-General

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Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

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[ 1647-16-1 ]