66823-04-9

Basic information

• Product Name: (1R,2S)-2-(Hydroxymethyl)-1-phenylcyclopropanecarboxylic acid
• Synonyms: (1R,2S)-2-(Hydroxymethyl)-1-phenylcyclopropanecarboxylic acid;(1R,2S)-rel-2-(Hydroxymethyl)-1-phenylcyclopropanecarboxylic acid
• CAS NO: 66823-04-9
• Molecular Formula: C₁₁H₁₂O₃
• Molecular Weight: 192.21
• EINECS: 1533716-785-6
• Mol File: 66823-04-9.mol

Chemical Properties

• Melting Point: 145 ºC
• Boiling Point: 382.099°C at 760 mmHg
• Flash Point: 199.06°C
• Appearance: /
• Density: 1.310
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.605
• CAS DataBase Reference: (1R,2S)-2-(Hydroxymethyl)-1-phenylcyclopropanecarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2S)-2-(Hydroxymethyl)-1-phenylcyclopropanecarboxylic acid(66823-04-9)
• EPA Substance Registry System: (1R,2S)-2-(Hydroxymethyl)-1-phenylcyclopropanecarboxylic acid(66823-04-9)

Safety Data

• Hazardous Substances Data: 66823-04-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(1R,2S)-2-(Hydroxymethyl)-1-phenylcyclopropanecarboxylic acid is used as a synthetic intermediate for the preparation of various organic compounds. Its unique structure allows for versatile chemical reactions, making it a valuable building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Medicinal Chemistry:
In the pharmaceutical industry, (1R,2S)-2-(Hydroxymethyl)-1-phenylcyclopropanecarboxylic acid is used as a lead compound for the development of new drugs. Its specific configuration and functional groups may offer unique biological activities, which can be further optimized through medicinal chemistry approaches to treat various diseases and medical conditions.
Used in Drug Design and Development:
(1R,2S)-2-(Hydroxymethyl)-1-phenylcyclopropanecarboxylic acid is utilized as a structural motif in drug design, providing a foundation for the creation of novel therapeutic agents. Its carboxylic acid and hydroxymethyl groups can be exploited for the formation of hydrogen bonds and other non-covalent interactions, which are crucial for molecular recognition and binding to biological targets.
Used in Chemical Research:
In the field of chemical research, (1R,2S)-2-(Hydroxymethyl)-1-phenylcyclopropanecarboxylic acid serves as a model compound for studying the reactivity and selectivity of cyclopropane derivatives. Its unique configuration and functional groups offer opportunities to explore new reaction pathways and mechanisms, contributing to the advancement of organic chemistry.
Overall, (1R,2S)-2-(Hydroxymethyl)-1-phenylcyclopropanecarboxylic acid is a promising compound with potential applications across various industries. Its unique structure and properties make it a valuable asset in the development of new materials, pharmaceuticals, and chemical processes. Further research and development are essential to fully harness its potential and unlock its full range of applications.

InChI:InChI=1/C11H12O3/c12-7-9-6-11(9,10(13)14)8-4-2-1-3-5-8/h1-5,9,12H,6-7H2,(H,13,14)/t9-,11+/m1/s1

Upstream product

• 51594-55-9 (R)-(-)-epichlorohydrin 
• 140-29-4 phenylacetonitrile 
• 67843-74-7 (S)-epichlorohydrin 
• 63106-93-4 (1S,5R)-1-phenyl-3-oxabicyclo[3.1.0]hexan-2-one 

Downstream Products

• 175131-61-0 C₁₅H₂₂N₂O*ClH 
• 1237261-65-2 (1S,2R)-2-((1,3-dioxoisoindolin-2-yl)methyl)-N,N-diethyl-1-phenylcyclopropanecarboxamide-cyclopropanecarboxamide 
• 63106-93-4 (1S,5R)-1-phenyl-3-oxabicyclo[3.1.0]hexan-2-one 
• 101152-94-7 (1S,2R)-milnacipran hydrochloride 

Relevant articles and documents

Preparation method of levomilnacipran diastereoisomer

The invention provides a preparation method of a levomilnacipran diastereoisomer. The preparation method comprises the following steps: taking benzyl cyanide and R-epichlorohydrin or S-epichlorohydrinas starting materials, performing cycloalkylation on th

(+)-Methyl (1 R, 2S)-2-{[4-(4-Chlorophenyl)-4-hydroxypiperidin-1-yl]methyl}-1-phenylcyclopropanecarboxylate [(+)-MR200] derivatives as potent and selective sigma receptor ligands: Stereochemistry and pharmacological properties

Methoxycarbonyl-1-phenyl-2-cyclopropylmethyl based derivatives cis-(+)-1a [cis-(+)-MR200], cis-(-)-1a [cis-(-)-MR201], and trans-(±)-1a [trans-(±)-MR204], have been identified as new potent sigma (σ) receptor ligands. In the present paper, novel enantiomerically pure analogues were synthesized and optimized for their σ receptor affinity and selectivity. Docking studies rationalized the results obtained in the radioligand binding assay. Absolute stereochemistry was unequivocally established by X-ray analysis of precursor trans-(+)-5a as camphorsulfonyl derivative 9. The most promising compound, trans-(+)-1d, showed remarkable selectivity over a panel of more than 15 receptors as well as good chemical and enzymatic stability in human plasma. An in vivo evaluation evidenced that trans-(+)-1d, in contrast to trans-(-)-1d, cis-(+)-1d, or cis-(-)-1d, which behave as σ1 antagonists, exhibited a σ1 agonist profile. These data clearly demonstrated that compound trans-(+)-1d, due to its σ1 agonist activity and favorable receptor selectivity and stability, provided an useful tool for the study of σ1 receptors.

PROCESS FOR THE PREPARATION OF (1S,2R)-MILNACIPRAN

The invention relates to a process for the preparation of Levomilnacipran, a compound useful in the treatment of depression, comprising the following steps: a) directly converting the enantiomerically enriched form of alcohol (D) into the enantiomerically enriched form of the phthalimido derivative (C) by treatment with phthalimide in the presence of a trialkyl or triarylphosphine and of a dialkyl azodicarboxylate, formula (I) wherein the amount of phthalimide is comprised between 1 and 1.3 equivalents with respect to the molar amount of alcohol (D) used, and the amounts of both the phosphine and the azodicarboxylate are comprised, independently from each other, between 1 and 1.5 equivalents with respect to the molar amount of alcohol (D) used; b) deblocking the enantiomerically enriched form of the phthalimido derivative (C) to obtain Levomilnacipran, formula (II).

Conformational restriction approach to β-Secretase (BACE1) inhibitors: Effect of a cyclopropane ring to induce an alternative binding mode

Improvement of a drugs binding activity using the conformational restriction approach with sp3 hybridized carbon is becoming a key strategy in drug discovery. We applied this approach to BACE1 inhibitors and designed four stereoisomeric cyclopropane compounds in which the ethylene linker of a known amidine-type inhibitor 2 was replaced with chiral cyclopropane rings. The synthesis and biologic evaluation of these compounds revealed that the cis-(1S,2R) isomer 6 exhibited the most potent BACE1 inhibitory activity among them. X-ray structure analysis of the complex of 6 and BACE1 revealed that its unique binding mode is due to the apparent CH-π interaction between the rigid cyclopropane ring and the Tyr71 side chain. A derivatization study using 6 as a lead molecule led to the development of highly potent inhibitors in which the structure-activity relationship as well as the binding mode of the compounds clearly differ from those of known amidine-type inhibitors.