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[ CAS No. 6627-89-0 ] {[proInfo.proName]}

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Chemical Structure| 6627-89-0
Chemical Structure| 6627-89-0
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Product Details of [ 6627-89-0 ]

CAS No. :6627-89-0 MDL No. :MFCD00008804
Formula : C11H14O3 Boiling Point : -
Linear Structure Formula :- InChI Key :UXWVQHXKKOGTSY-UHFFFAOYSA-N
M.W : 194.23 Pubchem ID :81113
Synonyms :

Calculated chemistry of [ 6627-89-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.36
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 53.87
TPSA : 35.53 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.31 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.79
Log Po/w (XLOGP3) : 3.06
Log Po/w (WLOGP) : 3.0
Log Po/w (MLOGP) : 2.37
Log Po/w (SILICOS-IT) : 1.97
Consensus Log Po/w : 2.64

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.03
Solubility : 0.183 mg/ml ; 0.000944 mol/l
Class : Soluble
Log S (Ali) : -3.47
Solubility : 0.0654 mg/ml ; 0.000337 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.04
Solubility : 0.177 mg/ml ; 0.00091 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.06

Safety of [ 6627-89-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 6627-89-0 ]

* 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 [ 6627-89-0 ]
  • Downstream synthetic route of [ 6627-89-0 ]

[ 6627-89-0 ] Synthesis Path-Upstream   1~29

  • 1
  • [ 109-97-7 ]
  • [ 6627-89-0 ]
  • [ 5176-27-2 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1986, p. 2181 - 2186
[2] Tetrahedron Letters, 2008, vol. 49, # 22, p. 3691 - 3696
  • 2
  • [ 6627-89-0 ]
  • [ 870-46-2 ]
Reference: [1] Tetrahedron Letters, 1991, vol. 32, # 26, p. 3079 - 3082
[2] Journal of the American Chemical Society, 1957, vol. 79, p. 98,100
[3] Org. Synth. Coll. Vol. V <1973> 168,
  • 3
  • [ 6627-89-0 ]
  • [ 110-60-1 ]
  • [ 68076-36-8 ]
Reference: [1] Biomacromolecules, 2015, vol. 16, # 9, p. 3033 - 3041
[2] Synthesis, 2002, # 15, p. 2195 - 2202
[3] Organic Syntheses, 2007, vol. 84, p. 209 - 214
[4] Organic Letters, 2012, vol. 14, # 24, p. 6298 - 6301
[5] Organic and Biomolecular Chemistry, 2008, vol. 6, # 16, p. 2988 - 2994
  • 4
  • [ 6627-89-0 ]
  • [ 24469-50-9 ]
Reference: [1] Journal of the American Chemical Society, 1957, vol. 79, p. 98,100
  • 5
  • [ 6627-89-0 ]
  • [ 929-17-9 ]
  • [ 60142-89-4 ]
Reference: [1] Patent: US4133805, 1979, A,
  • 6
  • [ 124-09-4 ]
  • [ 6627-89-0 ]
  • [ 51857-17-1 ]
YieldReaction ConditionsOperation in experiment
46%
Stage #1: at 78℃; Inert atmosphere
Stage #2: With hydrogenchloride In dichloromethane; water
Stage #3: With sodium hydroxide In dichloromethane; water
tert-Butyl phenyl carbonate (25.6OmL, 138.0 mmoles) was added to a stirred solution of 1,6- diaminohexane (15.3Og, 131.7 mmoles) in absolute EtOH (15OmL) in a 25OmL RB flask. The apparatus was fitted with a condenser and heated to 780C overnight under a blanket of nitrogen and then allowed to cool to room temperature. The solvent was stripped off the reaction mixture in vacuo (rotary evaporator) yielding a pale pink oily residue. CH2Cl2 (20OmL) was added to the residue and the resultant solution extracted with 3>;<;200mL portions of de-ionised water. For each extraction the pH of the aqueous phase was monitored and adjusted with HCl(aq, 2M) such that the pH of the aqueous layer was 3 <; pH <; 7 [only required for 1st extraction, needing ca. 60-7OmL HCl(aq, 2M)]. The aqueous phases were collected in a Erlenmeyer flask containing aqueous NaOH (aq, 10OmL, 3M). Ensuring that the pH of the collected aqueous extracts was >;14 the resulting aqueous phase was extracted with CH2Cl2 (3>;<;150mL). These organic phases were recombined, evaporated to a volume of ca. 20OmL and subjected to the above pH modulated purification protocol for a second time by first extracting with water [3χ200mL, 3 <; pH <; 7 modulation with HCl(aq, 2M), again only required for 1st extract needing ca. 45-55mL HCl(aq, 2M)], basicifying these aqueous extracts with NaOH (10OmL, 3M) and extracting with CH2Cl2 (3 x 15OmL). The CH2Cl2 extracts were combined, reduced in volume to 20OmL and then dried over anhydrous MgSO4, filtered, and stripped to dryness on a rotary evaporator for a period of 20 minutes to yield 6-(tert-butoxycarbonylamino)hexylamine as a peach oil. This peach oil was then subjected to a short path distillation using a Kugelrohr apparatus with an oven temperature of 18O0C and at a vacuum pressure of 0.160 torr, the receiver bulb was cooled by means of a dry-ice / acetone bath. Yield: 13. Ig (46percent, colourless oil). 1H NMR (CDCl3) δ 1.14 (s, 2H, -NH2), 1.26-1.37 (m, 4H, -CH2-), 1.37-1.52 (s+m, 9H+4H, f-Bu + -CH2-), 2.67 (t, 2H, >;NCH2-), 3.09 (q, 2H, -C(O)NCH2-), 4.60 (bs, IH, -C(O)NH-).
Reference: [1] Synthesis, 2002, # 15, p. 2195 - 2202
[2] Organic Syntheses, 2007, vol. 84, p. 209 - 214
[3] Patent: WO2010/116142, 2010, A2, . Location in patent: Page/Page column 69-70
[4] Chemical Communications, 2009, # 43, p. 6557 - 6559
[5] Organic and Biomolecular Chemistry, 2008, vol. 6, # 16, p. 2988 - 2994
[6] Patent: US2013/281515, 2013, A1, . Location in patent: Paragraph 0180; 0181
  • 7
  • [ 2212-75-1 ]
  • [ 6627-89-0 ]
  • [ 2389-60-8 ]
Reference: [1] Synthetic Communications, 1981, vol. 11, # 4, p. 303 - 314
  • 8
  • [ 6627-89-0 ]
  • [ 2418-95-3 ]
Reference: [1] Synthetic Communications, 1981, vol. 11, # 4, p. 303 - 314
  • 9
  • [ 95-14-7 ]
  • [ 6627-89-0 ]
  • [ 657-27-2 ]
  • [ 2418-95-3 ]
YieldReaction ConditionsOperation in experiment
~ 75 %Spectr. at 60℃; for 18 h; A solution of L-lysine monohydrochloride (20.0 g, 109.5 mmol) and benzotriazole (14.3 g, 120.0 mmol) in a mixture of water (66.6 mL) and THF (111.0 mL) at pH 12 was treated with t-butyl phenyl carbonate (24.3 mL, 131.4 mmol) and stirred 18 hours at 600C. The mixture, initially 2 layers, became a clear orange solution and the product was approximately 75percent (NMR) .
Reference: [1] Patent: WO2008/14811, 2008, A1, . Location in patent: Page/Page column 16
  • 10
  • [ 24424-99-5 ]
  • [ 108-95-2 ]
  • [ 6627-89-0 ]
YieldReaction ConditionsOperation in experiment
95% at 20℃; for 16 h; General procedure: Boc2O (1.0 mmol) was added to a mixture of phenol or amine (1.0 mmol) andMgBr2 · OEt2 (0.1 mmol) in a round-bottom flask, at which point an evolution of gas occurs, and the reaction mixture was stirred magnetically at room temperature (ifnecessary, reactions was heated to∼60 °C). After complete consumption of the phenolor amine (by thin-layer chromatography, TLC; 3–16 h), the reaction mixture wasdiluted with water and extracted with EtOAc (3 × 20mL), and the combined EtOAcextracts were dried with Na2SO4 and concentrated under vacuum rotary evaporation.The residue was isolated by column chromatography through a bed of silicagel and eluted with 5–30percent ethyl acetate in hexane to afford the desired Bocprotectedproduct.
80% for 0.05 h; Microwave irradiation; Green chemistry General procedure: In an Erlenmeyer flask, we reacted the 1(eq) of hydroxyl compound with 1.1(eq) of (Boc)2O in the absence of any catalyst and any solvent under microwave irradiation in 300W. The reaction was monitored by TLC after 3-5min. 5 cm3 of diethyl ether was added to the mixture, the resulting tert-butanol was freely soluble in diethyl ether and the O-Boc product was crystallized. Purification of the product was accomplished by recrystallization from diethyl ether to give the O-Boc derivatives in good to excellent yields.
Reference: [1] Green Chemistry, 2011, vol. 13, # 2, p. 436 - 443
[2] Canadian Journal of Chemistry, 1985, vol. 63, p. 153 - 162
[3] Canadian Journal of Chemistry, 1985, vol. 63, p. 153 - 162
[4] Organic Letters, 2005, vol. 7, # 3, p. 427 - 430
[5] Synlett, 2006, # 13, p. 2104 - 2108
[6] Synthesis, 2008, # 9, p. 1448 - 1454
[7] Synthetic Communications, 2015, vol. 45, # 5, p. 653 - 660
[8] Tetrahedron Letters, 2004, vol. 45, # 3, p. 495 - 499
[9] RSC Advances, 2014, vol. 4, # 47, p. 24544 - 24550
[10] Tetrahedron Letters, 2010, vol. 51, # 52, p. 6915 - 6917
[11] Journal of Organic Chemistry, 2008, vol. 73, # 21, p. 8615 - 8618
[12] Applied Organometallic Chemistry, 2012, vol. 26, # 8, p. 395 - 400
[13] Journal of the American Chemical Society, 2009, vol. 131, p. 6902 - 6903
[14] Chemistry Letters, 2014, vol. 43, # 6, p. 851 - 853
[15] Tetrahedron Letters, 2008, vol. 49, # 27, p. 4249 - 4251
[16] Tetrahedron Letters, 2008, vol. 49, # 27, p. 4249 - 4251
[17] ChemMedChem, 2018, vol. 13, # 18, p. 1957 - 1971
  • 11
  • [ 1885-14-9 ]
  • [ 75-65-0 ]
  • [ 6627-89-0 ]
Reference: [1] Journal of Organic Chemistry, 2016, vol. 81, # 10, p. 4134 - 4141
[2] Journal of the American Chemical Society, 1957, vol. 79, p. 98,100
[3] Australian Journal of Chemistry, 1980, vol. 33, # 3, p. 481 - 490
  • 12
  • [ 404586-94-3 ]
  • [ 108-95-2 ]
  • [ 6627-89-0 ]
Reference: [1] Organic Letters, 2002, vol. 4, # 4, p. 585 - 587
[2] Tetrahedron, 2006, vol. 62, # 50, p. 11599 - 11607
  • 13
  • [ 865-47-4 ]
  • [ 88345-85-1 ]
  • [ 1008-89-5 ]
  • [ 6627-89-0 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1983, vol. 20, p. 1239 - 1243
  • 14
  • [ 264255-59-6 ]
  • [ 108-95-2 ]
  • [ 6627-89-0 ]
Reference: [1] Tetrahedron, 2006, vol. 62, # 50, p. 11599 - 11607
  • 15
  • [ 90731-83-2 ]
  • [ 6627-89-0 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1983, vol. 20, p. 1239 - 1243
  • 16
  • [ 1885-14-9 ]
  • [ 6627-89-0 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1983, vol. 20, p. 1239 - 1243
  • 17
  • [ 6627-89-0 ]
  • [ 109-76-2 ]
  • [ 75178-96-0 ]
Reference: [1] Tetrahedron Letters, 2008, vol. 49, # 41, p. 6003 - 6006
[2] Synthesis, 2002, # 15, p. 2195 - 2202
[3] Organic Syntheses, 2007, vol. 84, p. 209 - 214
[4] Organic Letters, 2012, vol. 14, # 24, p. 6298 - 6301
  • 18
  • [ 462-94-2 ]
  • [ 6627-89-0 ]
  • [ 51644-96-3 ]
Reference: [1] Medicinal Chemistry letters, 2012, vol. 3, # 8, p. 640 - 644,5
[2] ACS Medicinal Chemistry Letters, 2012, vol. 3, # 8, p. 640 - 644
[3] Synthesis, 2002, # 15, p. 2195 - 2202
[4] Organic Syntheses, 2007, vol. 84, p. 209 - 214
  • 19
  • [ 6627-89-0 ]
  • [ 111-40-0 ]
  • [ 117499-16-8 ]
Reference: [1] Langmuir, 2015, vol. 30, # 50, p. 15364 - 15372
[2] ChemMedChem, 2018, vol. 13, # 18, p. 1957 - 1971
[3] Journal of Photochemistry and Photobiology A: Chemistry, 2016, vol. 314, p. 66 - 74
[4] Patent: CN104151248, 2016, B, . Location in patent: Paragraph 0035; 0036; 0037
  • 20
  • [ 539-48-0 ]
  • [ 6627-89-0 ]
  • [ 108468-00-4 ]
Reference: [1] Patent: US2013/281515, 2013, A1, . Location in patent: Paragraph 0178; 0179
  • 21
  • [ 929-59-9 ]
  • [ 6627-89-0 ]
  • [ 153086-78-3 ]
Reference: [1] Tetrahedron Letters, 2008, vol. 49, # 41, p. 6003 - 6006
  • 22
  • [ 6627-89-0 ]
  • [ 78-90-0 ]
  • [ 149632-73-5 ]
  • [ 255735-88-7 ]
Reference: [1] Patent: WO2011/41713, 2011, A2, . Location in patent: Page/Page column 229
  • 23
  • [ 4246-51-9 ]
  • [ 6627-89-0 ]
  • [ 194920-62-2 ]
Reference: [1] Biochimie, 2011, vol. 93, # 8, p. 1357 - 1367
  • 24
  • [ 6627-89-0 ]
  • [ 78-90-0 ]
  • [ 255735-88-7 ]
Reference: [1] Synthesis, 2002, # 15, p. 2195 - 2202
[2] Organic Letters, 2005, vol. 7, # 7, p. 1295 - 1298
[3] Organic Syntheses, 2007, vol. 84, p. 209 - 214
[4] Journal of Medicinal Chemistry, 2016, vol. 59, # 1, p. 264 - 281
  • 25
  • [ 6627-89-0 ]
  • [ 78-90-0 ]
  • [ 149632-73-5 ]
  • [ 255735-88-7 ]
Reference: [1] Patent: WO2011/41713, 2011, A2, . Location in patent: Page/Page column 229
  • 26
  • [ 6627-89-0 ]
  • [ 79286-79-6 ]
  • [ 186550-13-0 ]
YieldReaction ConditionsOperation in experiment
98% for 24 h; Intermediate 138; 1 ,1 -dimethylethyl 3-amino-1 -pyrrolidinecarboxylate; 3-pyrrolidinamine (500 mg, 5.80 mmol), Tert-butyl phenyl carbonate (1.24 g, 6.38 mmol) was dissolved in DMF (5 ml) and stirred for 24 hours. Water and HCI 1 N was added until pH=3. The mixture was washed with dichloromethane (2 times). NaOH 1 N was added to the aqueous phase until pH=1 1-12 and was extracted with dichloromethane (4 times). The <n="94"/>organic phase was dried over Na2SC>4, filtered and evaporated to give the title compound as light orange liquid (1.063 g, 98percent). LC/MS : m/z 187 (M+23)+, Rt: 1.54 min.
Reference: [1] Patent: WO2009/47240, 2009, A1, . Location in patent: Page/Page column 92-93
  • 27
  • [ 52488-36-5 ]
  • [ 6627-89-0 ]
  • [ 676448-17-2 ]
Reference: [1] Patent: WO2006/66172, 2006, A1, . Location in patent: Page/Page column 78-79
  • 28
  • [ 6627-89-0 ]
  • [ 19777-66-3 ]
  • [ 333743-54-7 ]
YieldReaction ConditionsOperation in experiment
50%
Stage #1: With sodium hydroxide In ethanol at 20℃; for 2 h;
Stage #2: for 24 h; Reflux
To a mixture of NaOH (8.82g; 0.2205mol) and 96percent ethanol (150ml) was added compound 1b (16.36g; 0.11mol), under vigorous stirring. After 2h the white precipitate was filtered of and to the filtrate was added tert-butyl phenylcarbonate (39.37g; 0.203mol). The mixture was refluxed for 24h and then concentrated in vacuo to a colorless oil. Water (175ml) was added to the oil and the pH was adjusted to 3 using 2M H2SO4. The aqueous phase was washed with CH2Cl2 (3×200ml) and then the pH was adjusted to 12 with 2M NaOH. The aqueous phase was then extracted with CH2Cl2 (4×200ml), the organic phases were collected, dried over Na2SO4, and concentrated to yield compound 2 as a colorless oil (9.58g; 50percent yield). 1H NMR (300MHz, CDCl3) δ=4.94 (s, 1H, BocHN–CH2–CH(CH3)–NH2), 3.17–3.07 (m, 1H, BocHN–CH2–CH(CH3)–NH2), 3.05–2.92 (m, 1H, BocHN–CH2–CH(CH3)–NH2), 1.42 (s, 9H, (CH3)3C–C(O)–NH–), 1.04 (d, 3H, BocHN–CH2–CH(CH3)–NH2, 2J=6.3). 13C NMR (126MHz, CDCl3) δ=156.24, 79.12, 48.53, 46.87, 28.39, 21.54. MS (FAB) m/z=175 [M+H]+.
Reference: [1] Tetrahedron, 2015, vol. 71, # 7, p. 1109 - 1116
[2] Patent: US2009/247519, 2009, A1, . Location in patent: Page/Page column 134
  • 29
  • [ 6627-89-0 ]
  • [ 590-88-5 ]
  • [ 878799-20-3 ]
Reference: [1] Journal of Medicinal Chemistry, 2016, vol. 59, # 1, p. 264 - 281
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