Home Cart 0 Sign in  
X

[ CAS No. 38862-24-7 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 38862-24-7
Chemical Structure| 38862-24-7
Chemical Structure| 38862-24-7
Structure of 38862-24-7 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 38862-24-7 ]

Related Doc. of [ 38862-24-7 ]

Alternatived Products of [ 38862-24-7 ]

Product Details of [ 38862-24-7 ]

CAS No. :38862-24-7 MDL No. :MFCD00078261
Formula : C7H7NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :YXMISKNUHHOXFT-UHFFFAOYSA-N
M.W : 169.13 Pubchem ID :181508
Synonyms :
N-Succinimidyl acrylate

Calculated chemistry of [ 38862-24-7 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.29
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 41.67
TPSA : 63.68 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.46 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.34
Log Po/w (XLOGP3) : -0.18
Log Po/w (WLOGP) : -0.6
Log Po/w (MLOGP) : 0.0
Log Po/w (SILICOS-IT) : 0.21
Consensus Log Po/w : 0.15

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.58
Solubility : 44.8 mg/ml ; 0.265 mol/l
Class : Very soluble
Log S (Ali) : -0.7
Solubility : 33.6 mg/ml ; 0.199 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.23
Solubility : 99.1 mg/ml ; 0.586 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.05

Safety of [ 38862-24-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P305+P351+P338 UN#:N/A
Hazard Statements:H302-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 38862-24-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 38862-24-7 ]
  • Downstream synthetic route of [ 38862-24-7 ]

[ 38862-24-7 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 6066-82-6 ]
  • [ 814-68-6 ]
  • [ 38862-24-7 ]
YieldReaction ConditionsOperation in experiment
70% With triethylamine In chloroform at 0℃; for 2.5 h; N-hydroxysuccinimide (10 g, 0.086 mol) and triethylamine (13.2 g, 0.129 mol) were dissolved in chloroform (130 mL) at 0 °C. Acryloyl chloride (8.6 g, 0.094 mol) was added dropwise over a period of 2 hours to the stirred reaction mixture.
The reaction is described in Scheme 1, .
After being stirred an additional 30 minutes at 0 °C, the solution was washed twice with 60 mL saturated NaCl aqueous solution, dried over MgSO4, filtered and concentrated so as to get a residual volume of 30 mL. An ethyl acetate/pentane mixture (14 mL, 1:3 v/v) was added and the temperature was maintained at 0 °C to induce NAS crystallization overnight (70percent yield).
1 H NMR (CDCl3) d (ppm): 2.95 (S, 4H, CH2CH2), 6.20 (m, 1 H, CH=CH2), 6.4 (m, 1H, CH=CH2) and 6.75 (m, 1 H, CH=CH2).
46% With triethylamine In chloroform at 12℃; for 2.5 h; Inert atmosphere 2,5-Dioxopyrrolidin-1 -yl acrylate (28)
To a cooled (ice-bath) solution of /V-hydroxysuccinimide (27) (6.41 g, 55.8 mmol) and NEt3 (8.5 ml_, 61.0 mmol) in CHCI3 (100 mL) was added acryloyl chloride (26) dropwise under argon. The temperature of the mixture was kept below 12°C during the addition. After stirring for 2.5 h, the reaction mixture was subsequently washed with ice-water (100 mL), water (100 mL), and brine (100 mL). The organic phase was dried over Na2S04, filtered, concentrated in vacuo to 15 mL, and filtered through a pad of celite. The celite was washed with CHCI3 (15 mL), the filtrate was diluted with EtOAc (2 mL) and petroleum ether (1 1 mL), and stored at -20 °C overnight. The formed precipitate was filtered off and dried in vacuo to yield 28 (4.30 g, 25.4 mmol, 46percent) as white needles.
Reference: [1] Journal of Medicinal Chemistry, 2018, vol. 61, # 10, p. 4528 - 4560
[2] Chemical Communications, 2014, vol. 50, # 95, p. 15045 - 15048
[3] Organic Letters, 2002, vol. 4, # 5, p. 737 - 740
[4] Chemical Communications, 2009, # 46, p. 7107 - 7109
[5] Journal of Medicinal Chemistry, 1995, vol. 38, # 21, p. 4179 - 4190
[6] Analytical Chemistry, 2003, vol. 75, # 7, p. 1658 - 1663
[7] Journal of Materials Chemistry, 2011, vol. 21, # 34, p. 12917 - 12926
[8] Patent: EP2960263, 2015, A1, . Location in patent: Paragraph 0098
[9] Angewandte Chemie - International Edition, 2018, vol. 57, # 6, p. 1557 - 1562[10] Angew. Chem., 2018, vol. 130, p. 1573 - 1578,6
[11] Organic Letters, 2014, vol. 16, # 15, p. 3974 - 3977
[12] Macromolecules, 2004, vol. 37, # 7, p. 2371 - 2382
[13] Patent: WO2015/136027, 2015, A1, . Location in patent: Page/Page column 48
[14] Journal of the American Chemical Society, 2003, vol. 125, # 2, p. 320 - 321
[15] Angewandte Chemie - International Edition, 2008, vol. 47, # 10, p. 1875 - 1878
[16] International Journal of Pharmaceutics, 2011, vol. 420, # 2, p. 333 - 340
[17] Angewandte Chemie - International Edition, 2017, vol. 56, # 14, p. 3880 - 3885[18] Angew. Chem., 2017, vol. 129, # 14, p. 3938 - 3943,6
  • 2
  • [ 6066-82-6 ]
  • [ 79-10-7 ]
  • [ 38862-24-7 ]
Reference: [1] Tetrahedron, 1998, vol. 54, # 14, p. 3489 - 3494
[2] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 19, p. 6841 - 6850
[3] Journal of the American Chemical Society, 2010, vol. 132, # 2, p. 472 - 483
  • 3
  • [ 123-56-8 ]
  • [ 814-68-6 ]
  • [ 38862-24-7 ]
Reference: [1] Journal of Polymer Science, Part A: Polymer Chemistry, 2011, vol. 49, # 6, p. 1341 - 1350
  • 4
  • [ 6066-82-6 ]
  • [ 79-10-7 ]
  • [ 2524-64-3 ]
  • [ 38862-24-7 ]
Reference: [1] Patent: US5734064, 1998, A,
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 38862-24-7 ]

Alkenes

Chemical Structure| 193269-82-8

[ 193269-82-8 ]

1,3-Dioxo-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindol-2(3H)-yl 4-nitrobenzyl carbonate

Similarity: 0.51

Amides

Chemical Structure| 14464-29-0

[ 14464-29-0 ]

2,5-Dioxopyrrolidin-1-yl acetate

Similarity: 0.92

Chemical Structure| 30364-60-4

[ 30364-60-4 ]

Bis(2,5-dioxopyrrolidin-1-yl) succinate

Similarity: 0.89

Chemical Structure| 68528-80-3

[ 68528-80-3 ]

Bis(2,5-dioxopyrrolidin-1-yl) octanedioate

Similarity: 0.87

Chemical Structure| 69888-86-4

[ 69888-86-4 ]

2,5-Dioxopyrrolidin-1-yl tetradecanoate

Similarity: 0.87

Chemical Structure| 27243-15-8

[ 27243-15-8 ]

N-(Chloroacetoxy)succinimide

Similarity: 0.81

Esters

Chemical Structure| 14464-29-0

[ 14464-29-0 ]

2,5-Dioxopyrrolidin-1-yl acetate

Similarity: 0.92

Chemical Structure| 30364-60-4

[ 30364-60-4 ]

Bis(2,5-dioxopyrrolidin-1-yl) succinate

Similarity: 0.89

Chemical Structure| 68528-80-3

[ 68528-80-3 ]

Bis(2,5-dioxopyrrolidin-1-yl) octanedioate

Similarity: 0.87

Chemical Structure| 69888-86-4

[ 69888-86-4 ]

2,5-Dioxopyrrolidin-1-yl tetradecanoate

Similarity: 0.87

Chemical Structure| 27243-15-8

[ 27243-15-8 ]

N-(Chloroacetoxy)succinimide

Similarity: 0.81

Related Parent Nucleus of
[ 38862-24-7 ]

Aliphatic Heterocycles

Chemical Structure| 14464-29-0

[ 14464-29-0 ]

2,5-Dioxopyrrolidin-1-yl acetate

Similarity: 0.92

Chemical Structure| 30364-60-4

[ 30364-60-4 ]

Bis(2,5-dioxopyrrolidin-1-yl) succinate

Similarity: 0.89

Chemical Structure| 68528-80-3

[ 68528-80-3 ]

Bis(2,5-dioxopyrrolidin-1-yl) octanedioate

Similarity: 0.87

Chemical Structure| 69888-86-4

[ 69888-86-4 ]

2,5-Dioxopyrrolidin-1-yl tetradecanoate

Similarity: 0.87

Chemical Structure| 27243-15-8

[ 27243-15-8 ]

N-(Chloroacetoxy)succinimide

Similarity: 0.81

Pyrrolidines

Chemical Structure| 14464-29-0

[ 14464-29-0 ]

2,5-Dioxopyrrolidin-1-yl acetate

Similarity: 0.92

Chemical Structure| 30364-60-4

[ 30364-60-4 ]

Bis(2,5-dioxopyrrolidin-1-yl) succinate

Similarity: 0.89

Chemical Structure| 68528-80-3

[ 68528-80-3 ]

Bis(2,5-dioxopyrrolidin-1-yl) octanedioate

Similarity: 0.87

Chemical Structure| 69888-86-4

[ 69888-86-4 ]

2,5-Dioxopyrrolidin-1-yl tetradecanoate

Similarity: 0.87

Chemical Structure| 27243-15-8

[ 27243-15-8 ]

N-(Chloroacetoxy)succinimide

Similarity: 0.81