Lindelofidine

Base Information

• Chemical Name: Lindelofidine
• CAS No.: 488-06-2
• Molecular Formula: C8H15NO
• Molecular Weight: 141.21
• UNII: B8448092FP,724IZ218GL
• Nikkaji Number: J15.950F
• Wikidata: Q105154676
• Mol file: 488-06-2.mol

Synonyms:Lindelofidine;(+/-)-Isoretronecanol;Isoretronecanol, (+/-)-;(+)-Lindelofidine;(+)-Isoretronecanol;Isoretronecanol, (+)-;B8448092FP;UNII-B8448092FP;1H-Pyrrolizine-1-methanol, hexahydro-, trans-;724IZ218GL;1H-Pyrrolizine-1-methanol, hexahydro-, (1R,7aR)-rel-;488-06-2;18929-90-3;1H-Pyrrolizine-1-methanol, hexahydro-, (1R,7aR)-;1H-Pyrrolizine-1-methanol, hexahydro-, (1R-trans)-;UNII-724IZ218GL

Chemical Property of Lindelofidine

Chemical Property:

• Boiling Point: 180 °C (0.05 mmHg)
• PSA: 23.47000
• LogP: 0.40090
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 141.115364102
• Heavy Atom Count: 10
• Complexity: 126

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2C(CCN2C1)CO
• Isomeric SMILES: C1C[C@@H]2[C@@H](CCN2C1)CO

Technology Process of Lindelofidine

There total 34 articles about Lindelofidine 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: 94.0%

ethyl (+)-8β-pyrrolizidine-1α-carboxylate (63527-08-2) → (+)-isoretronecanol (488-06-2)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; for 2h; Ambient temperature;

DOI:10.1039/P19810000909

Reference yield:

7-(hydroxymethyl)tetrahydro-1H-pyrrolizin-3(2H)-one (155140-67-3) → (+)-isoretronecanol (488-06-2) + (+)-laburnine (3348-73-0) + laburnine (526-64-7) + (-)-isoretronecanol (526-63-6)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 4.25h; Overall yield = 92 %; Overall yield = 25 mg; Inert atmosphere; Reflux;

DOI:10.1002/anie.201407185

Reference yield:

C10H19NO4 → (+)-isoretronecanol (488-06-2) + (+)-laburnine (3348-73-0) + laburnine (526-64-7) + (-)-isoretronecanol (526-63-6)

Guidance literature:

Multi-step reaction with 3 steps

1: toluene-4-sulfonic acid / acetonitrile / Inert atmosphere

2: sodium tetrahydroborate / methanol / 0.5 h / 0 °C / Inert atmosphere

3: lithium aluminium tetrahydride / tetrahydrofuran / 4.25 h / 0 °C / Inert atmosphere; Reflux

With sodium tetrahydroborate; lithium aluminium tetrahydride; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; acetonitrile;

DOI:10.1002/anie.201407185

upstream raw materials:

ethyl (+)-8β-pyrrolizidine-1α-carboxylate

(R)-2-((R)-3-Chloro-1-hydroxymethyl-propyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

(R)-2-[(R)-3-Chloro-1-((S)-4-isopropyl-2-thioxo-thiazolidine-3-carbonyl)-propyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

(R)-2-[(R)-1-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-3-chloro-propyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

Refernces

• 1、 Koulman, Albert,Seeliger, Claudine,Edwards, Patrick J.B.,Fraser, Karl,Simpson, Wayne,Johnson, Linda,Cao, Mingshu,Rasmussen, Susanne,Lane, Geoffrey A.. "E/Z-Thesinine-O-4′-α-rhamnoside, pyrrolizidine conjugates produced by grasses (Poaceae)". . p. 1927 - 1932. Retrieved 2008.
• 2、 Chen, Lin,Huang, Shuai,Li, Chun Ying,Gao, Feng,Zhou, Xian Li. "Pyrrolizidine alkaloids from Liparis nervosa with antitumor activity by modulation of autophagy and apoptosis". . p. 147 - 155. Retrieved 2018.
• 3、 Koley, Dipankar,Krishna, Yarkali,Srinivas, Kyatham,Khan, Afsar Ali,Kant, Ruchir. "Organocatalytic asymmetric mannich cyclization of hydroxylactams with acetals: Total syntheses of ( )-epilupinine, ( )-tashiromine, and ( )-trachelanthamidine". supporting information. p. 13196 - 13200. Retrieved 2015/02/19.