61229-03-6

Basic information

• Product Name: (S)-1,2-Epoxyheptane
• Synonyms: (S)-1,2-Epoxyheptane;(S)-2-Pentyloxirane, 90%
• CAS NO: 61229-03-6
• Molecular Formula: C₇H₁₄O
• Molecular Weight: 114.1855
• Mol File: 61229-03-6.mol
• Article Data: 23

Chemical Properties

• Boiling Point: 139.702 °C at 760 mmHg
• Flash Point: 33.926 °C
• Appearance: /
• Density: 0.869g/cm³
• Vapor Pressure: 7.911mmHg at 25°C
• Refractive Index: 1.432
• CAS DataBase Reference: (S)-1,2-Epoxyheptane(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-1,2-Epoxyheptane(61229-03-6)
• EPA Substance Registry System: (S)-1,2-Epoxyheptane(61229-03-6)

Safety Data

• Hazardous Substances Data: 61229-03-6(Hazardous Substances Data)

Usage

Description

(S)-1,2-Epoxyheptane, also known as (S)-Pentyl-oxirane, is a chiral organic compound characterized by the presence of an epoxy group. It is a colorless liquid with a distinctive odor and is a versatile building block in organic synthesis.

Uses

Used in Pharmaceutical Industry:
(S)-1,2-Epoxyheptane is used as a key intermediate in the synthesis of various bioactive compounds, including berkelic acid, a bioactive fungal metabolite with anticancer activity. Its unique stereochemistry and reactivity make it a valuable component in the development of new drugs and therapeutic agents.
Used in Organic Synthesis:
(S)-1,2-Epoxyheptane is used as a versatile building block in organic synthesis for the preparation of a wide range of chemical compounds. Its epoxy group can undergo various reactions, such as ring-opening and nucleophilic addition, enabling the synthesis of complex molecules with potential applications in various industries.

InChI:InChI=1/C7H14O/c1-2-3-4-5-7-6-8-7/h7H,2-6H2,1H3/t7-/m0/s1

Upstream product

• 61228-99-7 (S)-(+)-2,2-dimethyl-4-pentyl-1,3-dioxolane 
• 592-76-7 1-Heptene 
• 35116-16-6 2-chloro-heptanal 
• 81007-64-9 (S)-1-chloroheptane-2-ol 
• 135027-61-1 Toluene-4-sulfonic acid 3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-propyl ester 
• 147596-22-3 (E)-(hept-1-enyl)dimethylsilanol 
• 147596-21-2 1-heptenyldimethylsilane 
• 628-71-7 1-Heptyne 
• 152517-51-6 Chloro-acetic acid (S)-1-tert-butylsulfanylmethyl-hexyl ester 
• 152398-27-1 Chloro-acetic acid 1-tert-butylsulfanylmethyl-hexyl ester 
• 152398-24-8 1-tert-Butylsulfanyl-heptan-2-ol 
• 5063-65-0 1,2-epoxyheptane 
• 80800-66-4 (S)-2-hydroxyhept-1-yl 4-methylbenzenesulfonate 
• 61229-02-5 (S)-1-bromohept-2-yl acetate 

Downstream Products

• 61248-45-1 (6S)-6-pentyl-5,6-dihydro-2H-pyran-2-one 
• 551-11-1 dinoprost 
• 51388-75-1 (3aR,4R,5R,6a5)-4-[(E,3S)-3-Hydroxy-1-octenyl]perhydrocyclopenta[b]fura n-2,5-diol 
• 3391-86-4 (S)-oct-1-en-3-ol 
• 848609-05-2 (S)-Dec-1-yn-5-ol 
• 223734-62-1 2-[[(1S)-1-(3-butynyl)hexyl]oxy]tetrahydro-2H-pyran 
• 26818-05-3 (+)(R)-1-bromo-heptanol-(2) 
• 1224174-06-4 (R)-undec-1-en-6-ol 
• 186774-91-4 (S)-(+)-1-[3,5-bis(benzyloxy)phenyl]heptan-2-ol 
• 63357-97-1 (S)-γ-nonanolide 

Relevant articles and documents

Concise, scalable and enantioselective total synthesis of prostaglandins

Prostaglandins are among the most important natural isolates owing to their broad range of bioactivities and unique structures. However, current methods for the synthesis of prostaglandins suffer from low yields and lengthy steps. Here, we report a practicability-oriented synthetic strategy for the enantioselective and divergent synthesis of prostaglandins. In this approach, the multiply substituted five-membered rings in prostaglandins were constructed via the key enyne cycloisomerization with excellent selectivity (>20:1 d.r., 98% e.e.). The crucial chiral centre on the scaffold of the prostaglandins was installed using the asymmetric hydrogenation method (up to 98% yield and 98% e.e.). From our versatile common intermediates, a series of prostaglandins and related drugs could be produced in two steps, and fluprostenol could be prepared on a 20-gram scale. [Figure not available: see fulltext.]

Total synthesis of natural (?)- and unnatural (+)-Melearoride A

This communication details the first total synthesis of the 13-membered macrolide, (?)-Melearoride A, as well as unnatural (+)-Melearoride A. The synthesis features a concise 13 step synthesis (11 steps longest linear sequence) that offers flexible stereo-control and multiple opportunities for unnatural analog synthesis to delve into antifungal SAR. The route features a cuprate addition, an Evans asymmetric alkylation, and a ring-closing metathesis (RCM) to close the 13-membered macrocyclic core.

Total Synthesis of Emmyguyacins A and B, Potential Fusion Inhibitors of Influenza Virus

Fungal glycolipids emmyguyacins A and B inhibit the pH-dependent conformational change of hemaglutinin A during replication of the Influenza virus. Herein, we report the first total synthesis and structure confirmation of emmyguyacins A and B. Our efficient route, which involves regioselective functionalization of trehalose, allows rapid access to adequate amounts of chemically pure emmyguyacin analogues including the desoxylate derivatives for SAR studies.