WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 592639
Description: alpha-Conhydrine is a biochemical.
MedKoo Cat#: 592639
Chemical Formula: C8H17NO
Exact Mass: 143.131
Molecular Weight: 143.23
Elemental Analysis: C, 67.09; H, 11.96; N, 9.78; O, 11.17
This product is not in stock, which may be available by custom synthesis.
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IUPAC/Chemical Name: 2-Piperidinemethanol, alpha-ethyl-, (R-(R*,S*))- (9CI)
InChi Key: VCCAAURNBULZRR-JGVFFNPUSA-N
InChi Code: InChI=1S/C8H17NO/c1-2-8(10)7-5-3-4-6-9-7/h7-10H,2-6H2,1H3/t7-,8+/m0/s1
SMILES Code: O[C@H](CC)[C@H]1NCCCC1
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO
Shelf Life: >3 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.03.00
The following data is based on the product molecular weight 143.23 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
|Concentration / Solvent Volume / Mass||1 mg||5 mg||10 mg|
|1 mM||1.15 mL||5.76 mL||11.51 mL|
|5 mM||0.23 mL||1.15 mL||2.3 mL|
|10 mM||0.12 mL||0.58 mL||1.15 mL|
|50 mM||0.02 mL||0.12 mL||0.23 mL|
1: Jamieson AG, Sutherland A. Ether-directed, stereoselective aza-Claisen rearrangements: synthesis of the piperidine alkaloid, alpha-conhydrine. Org Lett. 2007 Apr 12;9(8):1609-11. Epub 2007 Mar 20. PubMed PMID: 17371038.
2: Voituriez A, Ferreira F, Chemla F. Short and efficient asymmetric synthesis of (-)-alpha-conhydrine. J Org Chem. 2007 Jul 6;72(14):5358-61. Epub 2007 Jun 8. PubMed PMID: 17555362.
3: Guerreiro P, Ratovelomanana-Vidal V, Genet JP. Asymmetric synthesis of hydroxylated pyrrolizidine, indolizidine, and (+)-alpha-conhydrine via ruthenium-catalyzed hydrogenation. Chirality. 2000 Jun;12(5-6):408-10. PubMed PMID: 10824162.
4: Deshmukh SC, Roy A, Talukdar P. Diastereoselective construction of syn-α-oxyamines via three-component α-oxyaldehyde-dibenzylamine-alkyne coupling reaction: application in the synthesis of (+)-β-conhydrine and its analogues. Org Biomol Chem. 2012 Oct 7;10(37):7536-44. doi: 10.1039/c2ob26007g. Epub 2012 Aug 13. PubMed PMID: 22890876.
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6: Liu S, Xie JH, Li W, Kong WL, Wang LX, Zhou QL. Highly enantioselective synthesis of chiral cyclic amino alcohols and conhydrine by ruthenium-catalyzed asymmetric hydrogenation. Org Lett. 2009 Nov 5;11(21):4994-7. doi: 10.1021/ol901605a. PubMed PMID: 19788265.
7: Beng TK, Gawley RE. Highly enantioselective catalytic dynamic resolution of N-Boc-2-lithiopiperidine: synthesis of (R)-(+)-N-Boc-pipecolic acid, (S)-(-)-coniine, (S)-(+)-pelletierine, (+)-beta-conhydrine, and (S)-(-)-ropivacaine and formal synthesis of (-)-lasubine II and (+)-cermizine C. J Am Chem Soc. 2010 Sep 8;132(35):12216-7. doi: 10.1021/ja105772z. PubMed PMID: 20806976; PubMed Central PMCID: PMC2945905.
8: MOLL F, AUTERHOFF H. [Hydrogen bonding by conhydrine, pseudoconhydrine and N-methylconhydrine]. Arch Pharm Ber Dtsch Pharm Ges. 1962 Jan;295/67:52-7. German. PubMed PMID: 14475192.
9: Petersen KS, Posner GH. Asymmetric, organocatalytic, three-step synthesis of gamma-hydroxy-(E)-alpha,beta-unsaturated sulfones and esters. Org Lett. 2008 Oct 16;10(20):4685-7. doi: 10.1021/ol8020513. Epub 2008 Sep 24. PubMed PMID: 18811178; PubMed Central PMCID: PMC2628291.