128300-12-9

Basic information

• Product Name: 3H-Benz[e]indole-3-carboxylic acid, 1-(chloromethyl)-1,2-dihydro-5-(phenylmethoxy)-, 1,1-dimethylethyl ester, (1R)-
• CAS NO: 128300-12-9
• Molecular Formula: C25H26ClNO3
• Molecular Weight: 423.939
• Mol File: 128300-12-9.mol

Chemical Properties

• CAS DataBase Reference: 3H-Benz[e]indole-3-carboxylic acid, 1-(chloromethyl)-1,2-dihydro-5-(phenylmethoxy)-, 1,1-dimethylethyl ester, (1R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3H-Benz[e]indole-3-carboxylic acid, 1-(chloromethyl)-1,2-dihydro-5-(phenylmethoxy)-, 1,1-dimethylethyl ester, (1R)-(128300-12-9)
• EPA Substance Registry System: 3H-Benz[e]indole-3-carboxylic acid, 1-(chloromethyl)-1,2-dihydro-5-(phenylmethoxy)-, 1,1-dimethylethyl ester, (1R)-(128300-12-9)

Safety Data

• Hazardous Substances Data: 128300-12-9(Hazardous Substances Data)

Upstream product

• 227084-59-5 (E/Z)-tert-butyl 4-(benzyloxy)-1-iodonaphthalene-2-yl(3-chloroallyl)carbamate 
• 122745-37-3 2-((tert-Butyloxycarbonyl)amino)-4-(benzyloxy)-1-bromonaphthalene 
• 122745-35-1 3-Amino-1-(benzyloxy)naphthalene 
• 128228-77-3 5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(hydroxymethyl)-1,2-dihydro-3H-benzindole, (R)-(-)-O-acetyl mandelate ester 
• 122745-39-5 5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(hydroxymethyl)-1,2-dihydro-3H-benzindole 
• 13802-40-9 1-Methoxy-3-nitronaphthalene 
• 19256-80-5 3-Nitro-1-naphthol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 128300-10-7 (-)-(1R)-5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(hydroxymethyl)-1,2-dihydro-3H-benzindole 
• 122745-45-3 N-(tert-butyloxycarbonyl)-N-(2-propynyl)-4-(benzyloxy)-1-bromo-2-naphthylamine 
• 122745-38-4 5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-methylidene-1,2-dihydro-3H-benzindole 
• 122745-36-2 N-(tert-butyloxycarbonyl)-4-(benzyloxy)-2-naphthylamine 
• 100-39-0 benzyl bromide 

Downstream Products

• 130008-89-8 3-(tert-butyloxycarbonyl)-1-(chloromethyl)-5-hydroxy-1,2-dihydro-3H-benzindole 
• 244241-92-7 C-(5-benzyloxy-1-chloromethyl-1,2-dihydro-benzo[e]indol-3-yl)-C-(5,6,7-trimethoxy-1H-indol-2-yl)-methyleneamine 
• 244241-91-6 (5-benzyloxy-1-chloromethyl-1,2-dihydro-benzo[e]indol-3-yl)-(5,6,7-trimethoxy-1H-indol-2-yl)-methanethione 
• 244241-90-5 (5-benzyloxy-1-chloromethyl-1,2-dihydro-benzo[e]indol-3-yl)-(5,6,7-trimethoxy-1H-indol-2-yl)-methanone 

Relevant articles and documents

METHODS AND COMPOUNDS FOR PREPARING CC-1065 ANALOGS

A method of forming a CBI CC- 1065 analog utilizes NH2 as a starting material, where R3 is H or alkyl and R6 is H, substituted or unsubstituted lower alkyl, cyano, or alkoxy. Intermediates (I) are used and are claimed.

Effective Asymmetric Synthesis of 1,2,9,9a-Tetrahydrocyclopropa[c]benzo[e]indol-4-one (CBI)

A short, asymmetric synthesis of the 1,2,9,9a-tetrahydrocyclopropa[c]benzo[e]indol-4-one (CBI) analogue of the CC-1065 and duocarmycin alkylation subunits is detailed that employs an effective enzymatic desymmetrization reaction of prochiral diol 12 using a commercially available Pseudomonas sp. lipase. The optically active monoacetate (S)-13 is furnished in exceptional conversions (88%) and optical purity (99% ee) and serves as an intermediate for the preparation of either enantiomer of CBI. Similarly, the Pseudomonas sp. lipase resolved the racemic intermediate 19, affording advanced intermediates of CBI in good conversions and optical purity (99% ee), and provided an alternative approach to the preparation of optically active CBI derivatives.

Resolution of a CBI precursor and incorporation into the synthesis of (+)-CBI, (+)-CBI-CDPI1, (+)-CBI-CDPI2: Enhanced functional analogs of (+)-CC-1065. A critical appraisal of a proposed relationship between electrophile reactivity,

Details of the resolution of an immediate CBI precursor, (+)- and (-)-8, and its subsequent incorporation into (+)- and (-)-CBI-CDPI(n), optically-active enhanced functional analogs of (+)-CC-1065, are described. In marked contrast to a previously detaile

Synthesis of N-(tert-Butyloxycarbonyl)-CBI, CBI, CBI-CDPI1, and CBI-CDPI2: Enhanced Functional Analogues of CC-1065 Incorporating the 1,2,9,9a-Tetrahydrocyclopropabenzindol-4-one (CBI) Left-Hand Subunit

Full details of the synthesis of N-(tert-butyloxycarbonyl)-1,2,9,9a-tetrahydrocyclopropabenzindol-4-one constituting a more stable functional analogue of the CC-1065 left-hand subunit are described.The resolution of an immediate CBI