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[ CAS No. 16369-05-4 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 16369-05-4
Chemical Structure| 16369-05-4
Chemical Structure| 16369-05-4
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Product Details of [ 16369-05-4 ]

CAS No. :16369-05-4 MDL No. :MFCD00004730
Formula : C5H13NO Boiling Point : -
Linear Structure Formula :NH2CH(CH(CH3)2)CH2OH InChI Key :-
M.W : 103.16 Pubchem ID :-
Synonyms :

Calculated chemistry of [ 16369-05-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 30.02
TPSA : 46.25 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.93 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.54
Log Po/w (XLOGP3) : 0.0
Log Po/w (WLOGP) : -0.04
Log Po/w (MLOGP) : 0.23
Log Po/w (SILICOS-IT) : -0.21
Consensus Log Po/w : 0.3

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.35
Solubility : 46.3 mg/ml ; 0.449 mol/l
Class : Very soluble
Log S (Ali) : -0.52
Solubility : 31.0 mg/ml ; 0.3 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.15
Solubility : 73.4 mg/ml ; 0.711 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 16369-05-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 16369-05-4 ]

* 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 [ 16369-05-4 ]
  • Downstream synthetic route of [ 16369-05-4 ]

[ 16369-05-4 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 516-06-3 ]
  • [ 16369-05-4 ]
Reference: [1] Synthetic Communications, 2000, vol. 30, # 23, p. 4387 - 4395
[2] Analytical Chemistry, 2001, vol. 73, # 4, p. 799 - 802
[3] Journal of Organic Chemistry, 1962, vol. 27, p. 1049
[4] Journal of Organic Chemistry, 1990, vol. 55, # 11, p. 3464 - 3474
[5] Journal of medicinal chemistry, 1966, vol. 9, # 6, p. 911 - 920
[6] Patent: US2003/153771, 2003, A1,
[7] Synlett, 2008, # 12, p. 1829 - 1832
[8] Patent: WO2017/176960, 2017, A1, . Location in patent: Paragraph 00779
  • 2
  • [ 13292-87-0 ]
  • [ 516-06-3 ]
  • [ 16369-05-4 ]
YieldReaction ConditionsOperation in experiment
62% With sodium hydroxide In tetrahydrofuran; water EXAMPLE 2
A dry, 12-liter glass reaction vessel equipped as described in Example 1 was charged with 900 grams (7.7 moles) of valine and 2.5 liters of tetrahydrofuran.
Using the procedure described in Example 1, boron trifluoride diethyl etherate (1.05 liters, 8.5 moles) was added followed by 0.85 liter (8.5 moles) of borane-dimethyl sulfide at reflux.
The addition took 8 hours and heating was continued for an additional 3 hours following the addition.
The reaction mixture was then hydrolyzed with 0.75 liter of tetrahydrofuran/water followed by 24.6 moles of sodium hydroxide as an aqueous solution.
The product was isolated as described in Example 1 giving 494 grams (62percent yield) of 2-amino-3-methyl-1-butanol, bp 78°-79°C at 8 mm, n20D 1.4543, purity by glc analysis: 97percent.
Reference: [1] Patent: US3935280, 1976, A,
  • 3
  • [ 4070-48-8 ]
  • [ 16369-05-4 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1979, p. 1230 - 1236
[2] Patent: US6369253, 2002, B1,
[3] Patent: US6048992, 2000, A,
  • 4
  • [ 17016-83-0 ]
  • [ 16369-05-4 ]
Reference: [1] Tetrahedron Letters, 2002, vol. 43, # 4, p. 557 - 559
  • 5
  • [ 13893-45-3 ]
  • [ 16369-05-4 ]
Reference: [1] Journal of Organic Chemistry, 1990, vol. 55, # 11, p. 3464 - 3474
[2] Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1954, vol. 296, p. 188,191
[3] Helvetica Chimica Acta, 1922, vol. 5, p. 478
[4] Journal of medicinal chemistry, 1966, vol. 9, # 6, p. 911 - 920
[5] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1985, p. 1961 - 1966
  • 6
  • [ 16940-66-2 ]
  • [ 72-18-4 ]
  • [ 16369-05-4 ]
Reference: [1] Patent: US2003/149264, 2003, A1,
[2] Patent: US2003/149264, 2003, A1,
[3] Patent: US2003/149264, 2003, A1,
  • 7
  • [ 77426-65-4 ]
  • [ 16369-05-4 ]
Reference: [1] Synthesis, 2003, # 13, p. 1965 - 1967
  • 8
  • [ 13474-14-1 ]
  • [ 16369-05-4 ]
Reference: [1] Tetrahedron Letters, 1994, vol. 35, # 11, p. 1777 - 1780
  • 9
  • [ 77392-54-2 ]
  • [ 16369-05-4 ]
Reference: [1] Journal of the Chemical Society, 1935, p. 410,414
  • 10
  • [ 56430-36-5 ]
  • [ 16369-05-4 ]
Reference: [1] Journal of the Chemical Society, 1935, p. 410,414
  • 11
  • [ 16369-05-4 ]
  • [ 4276-09-9 ]
Reference: [1] Journal of the American Chemical Society, 1984, vol. 106, # 25, p. 7729 - 7734
  • 12
  • [ 16369-05-4 ]
  • [ 591-07-1 ]
  • [ 95530-58-8 ]
Reference: [1] Patent: CN107253934, 2017, A, . Location in patent: Paragraph 0008; 0009
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Technical Information

• 1,4-Addition of an Amine to a Conjugated Enone • 1,4-Addition of an Amine to a Conjugated Enone • Add Hydrogen Cyanide to Aldehydes and Ketones to Produce Alcohols • Alcohol Syntheses from Aldehydes, Ketones and Organometallics • Alcohols are Weakly Basic • Alcohols as Acids • Alcohols Convert Acyl Chlorides into Esters • Alcohols from Haloalkanes by Acetate Substitution-Hydrolysis • Alcohols React with PX3 • Alcoholysis of Anhydrides • Aldehydes and Ketones Form Hemiacetals Reversibly • Aldol Addition • Alkene Hydration • Alkene Hydration • Amides Can Be Converted into Aldehydes • Amine Synthesis from Nitriles • Amine Synthesis from Nitriles • Amines Convert Acyl Chlorides into Amides • Amines Convert Esters into Amides • Appel Reaction • Azide Reduction by LiAlH4 • Azide Reduction by LiAlH4 • Base-Catalyzed Hydration of α,β -Unsaturated Aldehydes and Ketones • Basicity of Amines • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Carboxylic Acids React with Alcohols to Form Esters • Chan-Lam Coupling Reaction • Chichibabin Reaction • Chloroalkane Synthesis with SOCI2 • Chromium Reagents for Alcohol Oxidation • Chugaev Reaction • Claisen Condensations Produce β-Dicarbonyl Compounds • Claisen Condensations Produce β-Dicarbonyl Compounds • Convert Esters into Aldehydes Using a Milder Reducing Agent • Convert Haloalkanes into Alcohols by SN2 • Corey-Kim Oxidation • Decarboxylation of 3-Ketoacids Yields Ketones • Decomposition of Lithium Aluminum Hydride by Protic Solvents • Dess-Martin Oxidation • Diazotization Reaction • DIBAL Attack Nitriles to Give Ketones • Enamine Formation • Esters Are Reduced by LiAlH4 to Give Alcohols • Esters Hydrolyze to Carboxylic Acids and Alcohols • Ether Synthesis by Oxymercuration-Demercuration • Ethers Synthesis from Alcohols with Strong Acids • Formation of an Amide from an Amine and a Carboxylic Acid • Formation of an Amide from an Amine and a Carboxylic Acid • Friedel-Crafts Alkylations Using Alcohols • Geminal Diols and Acetals Can Be Hydrolyzed to Carbonyl Compounds • Grignard Reagents Transform Esters into Alcohols • Grignard Reagents Transform Esters into Alcohols • Haloalcohol Formation from an Alkene Through Electrophilic Addition • Halogen and Alcohols Add to Alkenes by Electrophilic Attack • Halogen and Alcohols Add to Alkenes by Electrophilic Attack • Hemiaminal Formation from Amines and Aldehydes or Ketones • Hemiaminal Formation from Amines and Aldehydes or Ketones • HIO4 Oxidatively Degrades Vicinal Diols to Give Carbonyl Derivatives • Hofmann Elimination • Hofmann Rearrangement • Hydration of the Carbonyl Group • Hydride Reductions • Hydride Reductions of Aldehydes and Ketones to Alcohols • Hydride Reductions of Aldehydes and Ketones to Alcohols • Hydroboration-Oxidation • Hydroboration-Oxidation • Hydrolysis of Haloalkanes • Hydrolysis of Imines to Aldehydes and Ketones • Imine Formation from Amines and Aldehydes or Ketones • Jones Oxidation • Ketones Undergo Mixed Claisen Reactions to Form β-Dicarbonyl Compounds • Leuckart-Wallach Reaction • Mannich Reaction • Martin's Sulfurane Dehydrating Reagent • Methylation of Ammonia • Methylation of Ammonia • Mitsunobu Reaction • Moffatt Oxidation • Nitrosation of Amines • Osmium Tetroxide Reacts with Alkenes to Give Vicinal Diols • Osmium TetroxideReacts with Alkenes to Give Vicinal Diols • Oxidation of Alcohols by DMSO • Oxymercuration-Demercuration • Peptide Bond Formation with DCC • Petasis Reaction • Preparation of Alcohols • Preparation of Alkenes by Dehydration of Alcohols • Preparation of Alkenes by Dehydration of Alcohols • Preparation of Alkoxides with Alkyllithium • Preparation of Amines • Preparation of LDA • Primary Ether Cleavage with Strong Nucleophilic Acids • Reactions of Alcohols • Reactions of Amines • Reactions with Organometallic Reagents • Reduction of an Amide to an Amine • Reduction of an Amide to an Amine • Reduction of an Ester to an Alcohol • Reduction of Carboxylic Acids by LiAlH4 • Reduction of Carboxylic Acids by Lithium Aluminum Hydride • Reduction of Carboxylic Acids by Lithium Aluminum Hydride • Reductive Amination • Reductive Amination • Ring Opening of an Oxacyclopropane by Lithium Aluminum Hydride • Ring Opening of Azacyclopropanes • Ring Opening of Azacyclopropanes • Ring Opening of Oxacyclobutanes • Ritter Reaction • Sharpless Olefin Synthesis • Specialized Acylation Reagents-Vilsmeier Reagent • Strecker Synthesis • Swern Oxidation • Synthesis of 2-Amino Nitriles • Synthesis of Alcohols from Tertiary Ethers • Synthesis of an Alkyl Sulfonate • The Nucleophilic Opening of Oxacyclopropanes • Thiazolium Salt Catalysis in Aldehyde Coupling • Thiazolium Salts Catalyze Aldehyde Coupling • Thiazolium Salts Catalyze Aldehyde Coupling • Transesterification • Ugi Reaction • Use 1,3-dithiane to Prepare of α-Hydroxyketones • Vicinal Anti Dihydroxylation of Alkenes • Williamson Ether Syntheses
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