39590-81-3

Basic information

• Product Name: 1,1-Bis(hydroxymethyl)cyclopropane
• Synonyms: CYCLOPROPYLIDENEDIMETHANOL;CYCLOPROPANE DIMETHANOL;1,1-BIS(HYDROXYMETHYL)CYCLOPROPANE;1,1-CYCLOPROPANEDIMETHANOL;1,1-DIMETHYLCYCLOPROPANE;(1-HYDROXYMETHYLCYCLOPROPYL)METHANOL;1,1-Cyclopropane dimethanlol;1,1-Cyclopropyldimethanol
• CAS NO: 39590-81-3
• Molecular Formula: C5H10O2
• Molecular Weight: 102.13
• Product Categories: Propanes/propenes;Hydroxymethyl's;Alkohols;API intermediates;Ring Systems;Thiophenes
• Mol File: 39590-81-3.mol

Chemical Properties

• Boiling Point: 235-236 °C(lit.)
• Flash Point: >230 °F
• Appearance: Liquid
• Density: 1.065 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00601mmHg at 25°C
• Refractive Index: n20/D 1.4700(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform, Ethyl Acetate (Slightly)
• PKA: 14.80±0.10(Predicted)
• CAS DataBase Reference: 1,1-Bis(hydroxymethyl)cyclopropane(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1-Bis(hydroxymethyl)cyclopropane(39590-81-3)
• EPA Substance Registry System: 1,1-Bis(hydroxymethyl)cyclopropane(39590-81-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 39590-81-3(Hazardous Substances Data)

Usage

Uses

1,1-Bis(hydroxymethyl)cyclopropane is used as a synthetic intermediate for the production of morphine alkaloids, which are important pharmaceutical compounds with potent analgesic and sedative effects. It is also utilized as an inhibitor of 5-lipoxygenase, an enzyme involved in the production of leukotrienes, which are inflammatory mediators. By inhibiting this enzyme, 1,1-Bis(hydroxymethyl)cyclopropane can potentially be used in the treatment of various inflammatory conditions.
Used in Pharmaceutical Industry:
1,1-Bis(hydroxymethyl)cyclopropane is used as a synthetic intermediate for the production of morphine alkaloids, which are essential in the development of potent analgesic and sedative medications. Its role in the synthesis of these alkaloids makes it a valuable component in the pharmaceutical industry.
Used in Enzyme Inhibition:
1,1-Bis(hydroxymethyl)cyclopropane is used as an inhibitor of 5-lipoxygenase, an enzyme that plays a crucial role in the synthesis of leukotrienes, which are involved in inflammatory processes. By inhibiting this enzyme, it can potentially be employed in the development of treatments for various inflammatory conditions, making it a valuable compound in the field of enzyme inhibition and inflammation management.

InChI:InChI=1/C5H10O2/c6-3-5(4-7)1-2-5/h6-7H,1-4H2

Upstream product

• 1559-02-0 diethyl cyclopropane-1,1-dicarboxylate 
• 148420-14-8 1,1-cyclopropanedimethanol diacetate 
• 1120-56-5 methylidenecyclobutane 
• 55754-69-3 [1-(chloromethyl)cyclopropyl]methanol 
• 6914-71-2 dimethyl 1,1-cyclopropanedicarboxylate 
• 7732-18-5 water 
• 304-59-6 Rochelle's salt 
• 598-10-7 cyclopropane-1,1-dicarboxylic acid 

Downstream Products

• 29086-41-7 1,1-bis(bromomethyl)cyclopropane 
• 101595-74-8 1,1-bis-benzenesulfonyloxymethyl-cyclopropane 
• 49640-66-6 1‐(hydroxymethyl)cyclopropane‐1‐carboxylic acid 
• 22308-08-3 cyclopropane-1,1-diyldimethanediyl bis(4-methylbenzenesulfonate) 
• 89729-09-9 5,7-dioxa-6-thia-spiro[2.5]octane 6-oxide 
• 83321-23-7 1,1-bis(iodomethyl)cyclopropane 
• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 148420-14-8 1,1-cyclopropanedimethanol diacetate 
• 136476-38-5 cyclopropane-1,1-diylbis(methylene) dimethanesulfonate 
• 152922-71-9 1-(hydroxymethyl)cyclopropaneacetonitrile 
• 598-10-7 cyclopropane-1,1-dicarboxylic acid 
• 177200-76-9 {1-[(benzyloxy)methyl]cyclopropyl}methanol 
• 208642-96-0 2-methanesulfonyl-benzenesulfonic acid 3-(1-hydroxymethyl-cyclopropylmethoxy)-5-methyl-phenyl ester 
• 288401-41-2 (S)-2-[(1-Benzyloxymethyl-cyclopropyl)-hydroxy-methyl]-3-isopropyl-6,8-dimethyl-nona-6,7-dienoic acid methyl ester 

Relevant articles and documents

Cyclopropyloxetanes. Reactions of 5-Oxaspirohexane with Hydrogen Halides

The title cyclopropyloxetane reacted with aqueous hydrogen chloride, bromide, and iodide to give mixtures of the corresponding 1-(halogenomethyl)-1-(hydroxymethyl)cyclopropane and 1-halogeno-1-(hydroxymethyl)cyclobutane.Keywords: Bicyclobutonium ion; Cyclopropyl carbinyl cation; Molecular rearrangement; Oxetane.

A Spiroalkylation Method for the Stereoselective Construction of α-Quaternary Carbons and Its Application to the Total Synthesis of (R)-Puraquinonic Acid

Cyclic α-quaternary carbon stereocenters were prepared from biselectrophillic substrates and an easily prepared chiral bicyclic sulfonyl lactam. This was achieved in two steps by spiroalkylation, employing biphasic reaction conditions with a phase-transfer catalyst, followed by reduction and alkylation with a series of alkyl halide electrophiles. The products of this method were isolated in good yields with with high levels of diastereoselectivity. This methodology was employed in the enantioselective total synthesis of (R)-puraquinonic acid (1) for a late-stage installation of the α-quaternary carbon stereocenter. This enabled the shortest synthesis of 1 to date, an eight-pot sequence providing an overall yield of 14%.

Preparing method for 1,1-cyclopropyl dimethyl carbinol

The invention belongs to the technical field of drug synthesis and relates to a preparing method for 1,1-cyclopropyl dimethyl carbinol. Specifically, the preparing method for the 1,1-cyclopropyl dimethyl carbinol includes the following steps that firstly, under the participation of a catalyst A, a solvent A and an acid-binding agent, diethyl malonate and 1,2-dichloroethane are used for preparing 1,1-cyclopropyl dioctyl phthalate diethyl ester; and secondly, under the participation of a solvent B and a catalyst B, a reducing agent is used for reducing the 1,1-cyclopropyl dioctyl phthalate diethyl ester, and the target product 1,1-cyclopropyl dimethyl carbinol is obtained. Raw materials adopted in the preparing method are cheap, easy to obtain and free of toxins, the activity of the catalysts are high, the solvents can be recycled, and the cost is obviously reduced; and reaction conditions are moderate, the products are easy to separate, the three industrial wastes are little, and the environment-friendly chemical requirement is met. In addition, according to the preparing method, the yield of the target product can be obviously increased, and the total recovery can reach 88% through the two steps.

Structure-activity relationship study of β-oxidation resistant indole-based 5-oxo-6,8,11,14-eicosatetraenoic acid (5-oxo-ETE) receptor antagonists

5-Oxo-6,8,11,14-eicosatetraenoic acid (5-oxo-ETE) is formed from 5S-hydroxy-6,8,11,14-eicosatetraenoic acid (5-HETE) by the 5-lipoxygenase (5-LO) pathway under conditions associated with oxidative stress. 5-Oxo-ETE is an important pro-inflammatory mediator, which stimulates the migration of eosinophils via a selective G-protein coupled receptor, known as the OXE receptor (OXE-R). Previously, we designed and synthesized structural mimics of 5-oxo-ETE such as 1 using an indole scaffold. In the present work, we added various substituents at C-3 of this moiety to block potential β-oxidation of the 5-oxo-valerate side chain, and investigated the structure-activity relationships of the resulting novel β-oxidation-resistant antagonists. Cyclopropyl and cyclobutyl substituents were well tolerated in this position, but were less potent as the highly active 3S-methyl compound. It seems likely that 3-alkyl substituents can affect the conformation of the 5-oxovalerate side chain containing the critical keto and carboxyl groups, thereby affecting interaction with the OXE-receptor.

Substituted 4-morpholine N-arylsulfonamides as γ-secretase inhibitors

The design, synthesis, SAR, and biological profile of a substituted 4-morpholine sulfonamide series of γ-secretase inhibitors (GSIs) were described. In several cases, the resulting series of GSIs reduced CYP liabilities and improved γ-secretase inhibition activity compared to our previous research series. Selected compounds demonstrated significant reduction of amyloid-β (Aβ) after acute oral dosing in a transgenic animal model of Alzheimer's disease (AD).

PYRROLOTRIAZINE INHIBITORS OF IRAK4 ACTIVITY

The present invention relates to pyrrolotriazine inhibitors of IRAK4 of formula (I) and provides compositions comprising such inhibitors, as well as methods therewith for treating IRAK4-mediated or -associated conditions or diseases.

PYRAZOLOPYRIMIDINE INHIBITORS OF IRAK4 ACTIVITY

The present invention relates to pyrazolopyrimidine inhibitors of IRAK4 of formula (I) and provides compositions comprising such inhibitors, as well as methods therewith for treating IRAK4-mediated or -associated conditions or diseases.

THIENOPYRAZINE INHIBITORS OF IRAK4 ACTIVITY

The present invention relates to thienopyrazine inhibitors of IRAK4 of formula (I) and provides compositions comprising such inhibitors, as well as methods therewith for treating IRAK4-mediated or -associated conditions or diseases.

PYRROLOPYRIDAZINE INHIBITORS OF IRAK4 ACTIVITY

The present invention relates to pyrrolopyridazine inhibitors of IRAK4 of formula (I) and provides compositions comprising such inhibitors, as well as methods therewith for treating IRAK4-mediated or -associated conditions or diseases.

BIARYL DERIVATIVES AS GPR120 AGONISTS

The present invention relates to biaryl derivatives of Formula 1, a method for preparing the same, a pharmaceutical composition comprising the same and use thereof. The biaryl derivatives of Formula 1 according to the present invention promote GLP-1 formation in the gastrointestinal tract and improve insulin resistance in the liver or in muscle due to anti-inflammatory action in macrophages, lipocytes, etc., and can accordingly be effectively used for preventing or treating diabetes, complications of diabetes, obesity, non-alcoholic fatty liver, steatohepatitis, osteoporosis or inflammation.