N-[(S)-1-(Hydroxymethyl)-2-propenyl]phthalimide

Base Information

• Chemical Name: N-[(S)-1-(Hydroxymethyl)-2-propenyl]phthalimide
• CAS No.: 174810-05-0
• Molecular Formula: C12H11NO3
• Molecular Weight: 217.224
• DSSTox Substance ID: DTXSID10451307
• Nikkaji Number: J783.105F
• Wikidata: Q82271271

Synonyms:174810-05-0;N-[(S)-1-(Hydroxymethyl)-2-propenyl]phthalimide;SCHEMBL15319789;DTXSID10451307;XWARCKJYBAUGMZ-QMMMGPOBSA-N;2-[(2S)-1-HYDROXYBUT-3-EN-2-YL]ISOINDOLE-1,3-DIONE;(S)-2-(1-hydroxybut-3-en-2-yl)isoindoline-1,3-dione

Chemical Property of N-[(S)-1-(Hydroxymethyl)-2-propenyl]phthalimide

Chemical Property:

• Melting Point: 56-57 °C(Solv: ligroine (8032-32-4); ethyl ether (60-29-7))
• Boiling Point: 382.2±35.0 °C(Predicted)
• PSA: 57.61000
• Density: 1.326±0.06 g/cm3(Predicted)
• LogP: 0.76740
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 217.07389321
• Heavy Atom Count: 16
• Complexity: 302

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C=CC(CO)N1C(=O)C2=CC=CC=C2C1=O
• Isomeric SMILES: C=C[C@@H](CO)N1C(=O)C2=CC=CC=C2C1=O

Technology Process of N-[(S)-1-(Hydroxymethyl)-2-propenyl]phthalimide

There total 1 articles about N-[(S)-1-(Hydroxymethyl)-2-propenyl]phthalimide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

4-vinyl-1,3-dioxolan-2-one (4427-96-7) + potassium phtalimide (1074-82-4) → (-)-2-[(1S)-(hydroxymethyl)prop-2-enyl]-1H-isoindole-1,3-(2H)-dione (174810-05-0) + (+)-2-[(1R)-(hydroxymethyl)prop-2-enyl]-1H-isoindole-1,3-(2H)-dione (174810-06-1)

Guidance literature:

With bis(η3-allyl-μ-chloropalladium(II)); C₄₃H₄₀O₂P₂; In tetrahydrofuran; at 20 ℃; for 23h; Overall yield = 96%; Optical yield = 89%ee; Inert atmosphere;

Reference yield: 98.0%

(S)-2-methoxy-2-phenylacetic acid (26164-26-1) + (-)-2-[(1S)-(hydroxymethyl)prop-2-enyl]-1H-isoindole-1,3-(2H)-dione (174810-05-0) → (S)-2-phthalimido-3-butenyl (S)-O-methylmandelate

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 25 ℃; for 12h;

DOI:10.1021/ja000547d

Reference yield: 98.0%

O-(4-methoxybenzyl)-trichloroacetimidate (89238-99-3) + (-)-2-[(1S)-(hydroxymethyl)prop-2-enyl]-1H-isoindole-1,3-(2H)-dione (174810-05-0) → (S)-2-(1-((4-methoxybenzyl)oxy)but-3-en-2-yl)isoindoline-1,3-dione (1315454-61-5)

Guidance literature:

With pyridinium p-toluenesulfonate; In dichloromethane; cyclohexane; at 20 ℃; for 23h; Inert atmosphere;

DOI:10.1002/chem.201003489

upstream raw materials:

4-vinyl-1,3-dioxolan-2-one

potassium phtalimide

Downstream raw materials:

2-(S)-N-phthalimido-3-buten-1-yl benzyl ether

(S)-2-(1-((4-methoxybenzyl)oxy)but-3-en-2-yl)isoindoline-1,3-dione

C₂₀H₂₁NO₆

tert-butyl [(1S)-1-(hydroxymethyl)prop-2-en-1-yl]carbamate

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