165817-09-4

Basic information

• Product Name: Acetic acid 5-(allyl-benzenesulfonyl-amino)-1-benzenesulfonyl-4-iodo-6-methoxy-2,3-dihydro-1H-indol-3-ylmethyl ester
• Synonyms: Acetic acid 5-(allyl-benzenesulfonyl-amino)-1-benzenesulfonyl-4-iodo-6-methoxy-2,3-dihydro-1H-indol-3-ylmethyl ester
• CAS NO: 165817-09-4
• Molecular Weight: 682.557
• Mol File: 165817-09-4.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: Acetic acid 5-(allyl-benzenesulfonyl-amino)-1-benzenesulfonyl-4-iodo-6-methoxy-2,3-dihydro-1H-indol-3-ylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Acetic acid 5-(allyl-benzenesulfonyl-amino)-1-benzenesulfonyl-4-iodo-6-methoxy-2,3-dihydro-1H-indol-3-ylmethyl ester(165817-09-4)
• EPA Substance Registry System: Acetic acid 5-(allyl-benzenesulfonyl-amino)-1-benzenesulfonyl-4-iodo-6-methoxy-2,3-dihydro-1H-indol-3-ylmethyl ester(165817-09-4)

Safety Data

• Hazardous Substances Data: 165817-09-4(Hazardous Substances Data)

Upstream product

• 214119-23-0 2-methoxy-N¹,N⁴-bis(phenylsulfonyl)-1,4-phenylenediamine 
• 5307-02-8 2-methoxy-1,4-phenylenediamine 
• 16618-66-9 2-bromo-6-methoxy-4-nitro-phenylamine 
• 108-24-7 acetic anhydride 
• 165817-08-3 N-Allyl-N-(1-benzenesulfonyl-3-hydroxymethyl-4-iodo-6-methoxy-2,3-dihydro-1H-indol-5-yl)-benzenesulfonamide 
• 127-09-3 sodium acetate 
• 97-52-9 2-methoxy-4-nitrophenylamine 
• 214119-28-5 N,N'-Diallyl-N,N'-dibenzenesulfonyl-6-bromo-2-methoxy-1,4-phenylenediamine 
• 214119-26-3 2-bromo-6-methoxy-N¹,N⁴-bis(phenylsulfonyl)-1,4-phenylenediamine 
• 214119-24-1 2-bromo-5-methoxy-N¹,N⁴-bis(phenylsulfonyl)-1,4-phenylenediamine 
• 214119-25-2 2-bromo-6-methoxy-1,4-phenylenediamine 
• 165817-07-2 N-Allyl-N-(1-benzenesulfonyl-4-iodo-3-iodomethyl-6-methoxy-2,3-dihydro-1H-indol-5-yl)-benzenesulfonamide 
• 165817-06-1 N,N'-Diallyl-N,N'-dibenzenesulfonyl-5-bromo-2-methoxy-1,4-phenylenediamine 
• 98-09-9 benzenesulfonyl chloride 

Downstream Products

• 112793-56-3 (1RS)-3-Benzenesulfonyl-5-hydroxy-1-hydroxymethyl-8-methyl-1,2-dihydro-3H-pyrrolo[3,2-e]indole 
• 214119-29-6 (1RS)-6-Benzenesulfonyl-3-benzenesulfonyl-5-hydroxy-1-hydroxymethyl-8-methyl-1,2-dihydro-3H-pyrrolo[3,2-e]indole 
• 165817-16-3 (1RS)-6-Benzenesulfonyl-3-benzenesulfonyl-5-hydroxy-1-acetoxymethyl-8-methyl-1,2-dihydro-3H-pyrrolo[3,2-e]indole 
• 165817-15-2 (1RS)-6-Benzenesulfonyl-3-benzenesulfonyl-5-methoxy-1-acetoxymethyl-8-methyl-1,2-dihydro-3H-pyrrolo[3,2-e]indole 
• 165817-13-0 (1RS)-6-Benzenesulfonyl-3-benzenesulfonyl-5-methoxy-1-acetoxymethyl-8-methylidene-1,2,7,8-tetrahydro-6H-pyrrolo[3,2-e]indole 

Relevant articles and documents

Efficient synthesis of the pharmacophore of the highly potent antitumor antibiotic CC-1065

The pharmacophore CPI (3) of the potent antitumor antibiotic CC-1065 (1) was synthesized in a very short reaction sequence of 11 steps with an overall yield of 23 %. The key steps are two consecutive cyclizations mediated by organotransition metal complexes, which form first the pyrroline and then the pyrrole ring in 3. Thus, halogen metal exchange of the N,N'-bisallylbromobenzene with tBuLi and subsequent reaction with Cp2ZrMeCl gave 11 as a single product in 60 % yield after quenching with two equivalents of iodine. Transformation of the iodomethyl group in 11 into an acetoxymethyl group, followed by Heck reaction, isomerization, and reductive cleavage, provided the pyrroloindoline system 4, which was converted into 3.