62296-04-2

Basic information

• Product Name: 1,3-Propanediol, 1-phenyl-, 1-acetate
• CAS NO: 62296-04-2
• Molecular Formula: C11H14O3
• Molecular Weight: 194.23
• Mol File: 62296-04-2.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: 1,3-Propanediol, 1-phenyl-, 1-acetate(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Propanediol, 1-phenyl-, 1-acetate(62296-04-2)
• EPA Substance Registry System: 1,3-Propanediol, 1-phenyl-, 1-acetate(62296-04-2)

Safety Data

• Hazardous Substances Data: 62296-04-2(Hazardous Substances Data)

Upstream product

• 155626-76-9 (1R,5S,3Z)-5-(N,N-dibenzylamino)-1-phenylhex-3-en-1-ol 
• 100-52-7 benzaldehyde 
• 1384833-85-5 (1R,5S,3Z)-1-acetoxy-5-(N,N-dibenzylamino)-1-phenylhex-3-ene 
• 132836-59-0 (1R,5S,3Z)-5-benzyloxy-1-phenylhex-3-en-1-ol 
• 119204-58-9 (4S,2E)-4-Phenylmethoxypent-2-enyl(tributyl)stannane 
• 132836-85-2 (1R,5S,3Z)-1-acetoxy-5-benzyloxy-1-phenyl-3-hexene 
• 873-49-4 cyclopropylbenzene 
• 563-68-8 thallium(I) acetate 

Downstream Products

• 103574-68-1 (R)-1-phenylpropane-1,3-diol mono-t-butyldimethylsilyl ether 
• 156327-45-6 (1R)-1-acetoxy-3-tert-butyldimethylsilyloxypropane 

Relevant articles and documents

1,5-Stereocontrol in tin(IV) halide mediated reactions between N- and S-substituted pent-2-enylstannanes and aldehydes or imines

Following transmetalation of (4S)-4-(dibenzylamino)pent-2-enyl(tributyl) stannane with tin(IV) bromide, reactions of the resulting allyltin tribromide with aldehydes gave (3Z)-1,5-syn-5-(dibenzylamino)hex-3-en-1-ols with excellent, ca. 98:2, stereocontrol. (4R)-5-Benzylthio-4-methylpent-2-enyl(tributyl) stannane similarly reacted with aldehydes to give (3Z)-1,5-anti-6-benzylthio-5- methylhex-3-en-1-ols with 87:13 stereocontrol. Although the analogous reaction of (4R)-4-benzylthiopent-2-enyl(tributyl)stannane with benzaldehyde proceeded with some stereoselectivity, 80-90:20-10, in favour of the (3Z)-1,5-syn- diastereoisomer, the yield was low due to a competing Lewis acid catalysed 1,4-elimination. N-Acylamino- and S-acylthio-pent-2-enylstannanes reacted with aldehydes with variable syn/anti-stereoselectivities. Tin(IV) chloride promoted reactions of the 4-(dibenzylamino)pent-2-enylstannane with 1- alkoxycarbonylimines gave (E)-alk-4-enoates with a modest preference for the 2,6-anti-products, 2,6-anti/2,6-syn=75:25.

1,9-Stereocontrol from 1,7-induction using an allylstannane followed by an Ireland-Claisen rearrangement

The 6-hydroxynona-2,7-dienylstananne 10 reacts with aldehydes after transmetallation with tin(IV) bromide with syn-selective 1,7-induction (1,7- syn : 1,7-anti = ca. 90 : 10). Ireland-Claisen rearrangements of the acetates 28a,b prepared from the syn-benz

1,6-Asymmetric induction in reactions between 6-hydroxy-6-methylhex-2-enyl(tributyl)stannane and aldehydes promoted by tin(IV) bromide

(R)-6-Hydroxy-5-methylhex-2-enyl(tributyl)stannane 4 transmetallates on treatment with tin(IV) bromide to give an intermediate allyltin tribromide which reacts with aldehydes to give 1-substituted (Z)-6-methylhept-2-ene-1,7-diols 7 with excellent anti-1,6