5b-Hydroxy-2,2,13b,13c-tetramethyl-2,3,5b,6,7,7a,8,13,13b,13c,14,15-dodecahydro-4h-3,15a-epoxy[1]benzoxepino[6',7':6,7]indeno[1,2-b]indol-4-one

Base Information

• Chemical Name: 5b-Hydroxy-2,2,13b,13c-tetramethyl-2,3,5b,6,7,7a,8,13,13b,13c,14,15-dodecahydro-4h-3,15a-epoxy[1]benzoxepino[6',7':6,7]indeno[1,2-b]indol-4-one
• CAS No.: 63722-91-8
• Molecular Formula: C27H31NO4
• Molecular Weight: 433.545
• DSSTox Substance ID: DTXSID00980176
• Wikidata: Q104943912
• Mol file: 63722-91-8.mol

Synonyms:5b-hydroxy-2,2,13b,13c-tetramethyl-2,3,5b,6,7,7a,8,13,13b,13c,14,15-dodecahydro-4h-3,15a-epoxy[1]benzoxepino[6',7':6,7]indeno[1,2-b]indol-4-one;DTXSID00980176;19-Hydroxy-4,5,24,24-tetramethyl-25,26-dioxa-7-azaheptacyclo[21.2.1.01,20.04,19.05,16.06,14.08,13]hexacosa-6(14),8,10,12,20-pentaen-22-one

Chemical Property of 5b-Hydroxy-2,2,13b,13c-tetramethyl-2,3,5b,6,7,7a,8,13,13b,13c,14,15-dodecahydro-4h-3,15a-epoxy[1]benzoxepino[6',7':6,7]indeno[1,2-b]indol-4-one

Chemical Property:

• Boiling Point: 631.8±55.0 °C(Predicted)
• PKA: 13.78±0.70(Predicted)
• PSA: 71.55000
• Density: 1.34±0.1 g/cm3(Predicted)
• LogP: 4.32230
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 433.22530847
• Heavy Atom Count: 32
• Complexity: 929

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1(C2C(=O)C=C3C4(CCC5CC6=C(C5(C4(CCC3(O2)O1)C)C)NC7=CC=CC=C67)O)C

Technology Process of 5b-Hydroxy-2,2,13b,13c-tetramethyl-2,3,5b,6,7,7a,8,13,13b,13c,14,15-dodecahydro-4h-3,15a-epoxy[1]benzoxepino[6',7':6,7]indeno[1,2-b]indol-4-one

There total 53 articles about 5b-Hydroxy-2,2,13b,13c-tetramethyl-2,3,5b,6,7,7a,8,13,13b,13c,14,15-dodecahydro-4h-3,15a-epoxy[1]benzoxepino[6',7':6,7]indeno[1,2-b]indol-4-one 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: 67.0%

C32H39NO6 (1440782-99-9) → Paspalinine (63722-91-8,138331-70-1)

Guidance literature:

With silica gel; In diethyl ether; at 90 - 110 ℃; for 3h; under 0.9976 Torr;

DOI:10.1002/anie.201206299

Reference yield: 44.0%

Paspalicine (11024-55-8,138331-69-8) → Paspalinine (63722-91-8,138331-70-1)

Guidance literature:

With selenium(IV) oxide; In 1,4-dioxane;

DOI:10.1021/ja00178a071

Reference yield: 40.0%

Paspalicine (11024-55-8,138331-69-8) → Paspalinine (63722-91-8,138331-70-1) + C27H31NO5 (138235-49-1)

Guidance literature:

With selenium(IV) oxide; In 1,4-dioxane; at 85 ℃; for 1.33333h;

DOI:10.1021/ja00030a046

upstream raw materials:

Paspalicine

C₂₇H₃₁NO₃

[(2S)-3,3-dimethyloxiran-2-yl]methanol

(S)-(3,3-dimethyl-1,4-dioxaspiro[4.4]nonan-2-yl)methanol

Downstream raw materials:

β-aflatrem

aflatrem

Refernces

• 1、 Enomoto, Masaru,Morita, Akira,Kuwahara, Shigefumi. "Total synthesis of the tremorgenic indole diterpene paspalinine". . p. 12833 - 12836. Retrieved 2013/02/23.
• 2、 Smith III,Sunazuka,Leenay,Kingery-Wood. "Total synthesis of (+)-paspalicine and (+)-paspalinine". . p. 8197 - 8198. Retrieved 2007/10/02.