122845-64-1

Basic information

• Product Name: Benzenamine, N-(cyclohexylmethylene)-4-methoxy-
• CAS NO: 122845-64-1
• Molecular Formula: C14H19NO
• Molecular Weight: 217.311
• Mol File: 122845-64-1.mol
• Article Data: 19

Chemical Properties

• CAS DataBase Reference: Benzenamine, N-(cyclohexylmethylene)-4-methoxy-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenamine, N-(cyclohexylmethylene)-4-methoxy-(122845-64-1)
• EPA Substance Registry System: Benzenamine, N-(cyclohexylmethylene)-4-methoxy-(122845-64-1)

Safety Data

• Hazardous Substances Data: 122845-64-1(Hazardous Substances Data)

Upstream product

• 104-94-9 4-methoxy-aniline 
• 2043-61-0 cyclohexanecarbaldehyde 
• 22700-44-3 diethyl (4-methoxyphenyl)phosphoramidate 

Downstream Products

• 315712-26-6 N-(4-methoxyphenyl)-cyclohexanecarboxamide 
• 865188-19-8 (1S)-1-cyclohexylbut-3-en-1-amine 
• 15144-80-6 N,N-diethyl-4-methoxyaniline 
• 6709-45-1 N-cyclohexylmethyl-p-anisidine 

Relevant articles and documents

New uses of amino acids as chiral building blocks in organic synthesis

(figure presented) N,N-Dibenzylamino aldehydes have emerged as a highly useful class of chiral building blocks in synthetic organic chemistry. We envisioned the transformation of the N,N-dibenzylamino aldehydes to the corresponding aldimines followed by d

A sustainable catalytic enantioselective synthesis of norstatine derivatives

Norstatine derivatives are of important value in pharmaceutical science. However, their catalytic asymmetric synthesis is rare. We developed a sustainable method via chiral phosphoric acid (CPA)-[Rh(OAc)2]2 co-catalyzed multi-component reactions (MCR) of diazoacetates with alcohol/water and imines. This method allows us to synthesize a library of 45 norstatines with excellent enanotioselectivites and broad substrate scope which includes anti-α-aryl-norstatines 11-1, anti-α-alkyl-norstatines 11-2, syn-α-hydro-norstatines 11-3 and syn-α-aryl-norstatines 11-4. The sustainability of this method lies in the reliable scalability, improved safety, and reusable [Rh(OAc)2]2 catalyst. The synthetic value of norstatine derivatives was demonstrated by preparing oxazolinone 14, ezetimibe analogue 15, and Taxol C-13 chain 16. Mechanistic study reveals that the synergetic catalysis of CPA and [Rh(OAc)2]2 is essential to maintain chemo- and enantioselectivity. Control experiments support the mechanism where the reactions proceed through the trapping of hyper-reactive oxonium ylides with imines. Shortly, we report herein the sustainable catalytic enantioselective synthesis of both syn- and anti-norstatine derivatives. We believe that this method might shed light on the sustainable synthesis of norstatine derivative-based drug candidates.

Asymmetric Petasis Borono-Mannich Allylation Reactions Catalyzed by Chiral Biphenols

Chiral biphenols catalyze the asymmetric Petasis borono-Mannich allylation of aldehydes and amines through the use of a bench-stable allyldioxaborolane. The reaction proceeds via a two-step, one-pot process and requires 2–8 mole % of 3,3′-Ph2-BINOL as the optimal catalyst. Under microwave heating the reaction affords chiral homoallylic amines in excellent yields (up to 99 %) and high enantioselectivies (er up to 99:1). The catalytic reaction is a true multicomponent condensation reaction whereas both the aldehyde and the amine can possess a wide range of structural and electronic properties. Use of crotyldioxaborolane in the reaction results in stereodivergent products with anti- and syn-diastereomers both in good diastereoselectivities and enantioselectivities from the corresponding E- and Z-borolane stereoisomers.