Synthesis of Bioactive Compounds from 3-Carene (II): Synthesis, Antifungal Activity and 3D-QSAR Study of (Z)- and (E)-3-Caren-5-One Oxime Sulfonates

Round 1

Reviewer 1 Report

The manuscript is interesting and well written. 

However, there are a few minor corrections to be made before final acceptance. 

Lines 84-88: 

The authors state that the 1H NMR signals of C4-H and C6-H are deshielded by their hydrogen bond interaction with the OH group oxygen. That cannot be right. Please check the references cited by Ref[28], or either those below:

M. Axelson, J. Sjovall, T. Drakenberg and S. Forsen, ANAL. LETT. B11(3), 229-237 (1978)

L.M. Jackman and S. Sternhell, "Applications of Nuclear Mag- n e t i c Resonance Spectroscopy i n Chemistry" 2nd Ed. , Pergamon Press, Oxford, 1969, p. 226.

Lines 195-196: 

Please consider:

3-Caren-5-one oxime was synthesized according to our previous work [21], and the separation conditions were explored and optimized.  

Please, explain HOW those conditions were optimized, and specify the optimized methodology here. 

Author Response

Response to Reviewer 1 Comments

 

Thank you for your nice comments on our article and we really appreciate your help. After this revision, we have written a point-by-point response letter to you as you can see above. In the revised version, changes to our manuscript were all highlighted within the document by using red colored text.

 

Point 1: The authors state that the 1H NMR signals of C4-H and C6-H are deshielded by their hydrogen bond interaction with the OH group oxygen. That cannot be right. Please check the references cited by Ref [28], or either those below:

M. Axelson, J. Sjovall, T. Drakenberg and S. Forsen, ANAL. LETT. 11(3), 229-237 (1978)

L.M. Jackman and S. Sternhell, "Applications of Nuclear Magnetic Resonance Spectroscopy in Chemistry" 2nd Ed. , Pergamon Press, Oxford, 1969, p. 226.

 

Response 1: Thank you for your reminding. The discussion associated with the 1H NMR signals has been revised.

 

Point 2: Please consider:

3-Caren-5-one oxime was synthesized according to our previous work [21], and the separation conditions were explored and optimized.

Please explain how those conditions were optimized, and specify the optimized methodology here.

 

Response 2: It was a mistake of expression and has been revised. Actually, we just improved the condition on the basis of our previous work [21] where the separation of 3a from 3b was difficult by silica gel column chromatography using a mixed solvent (EtOAc−petroleum ether = 1:60, v/v) as eluent. In this work, we found (Z)-3a can be separated easily by recrystallization from cyclohexane or petroleum ether with high yield, and (E)-3b can be separated easily from (Z)-3a by silica gel column chromatography (EtOAc−petroleum ether = 1:15, v/v) after 78% of (Z)-3a was recrystallized and filtrated.

Reviewer 2 Report

Review attached.

Comments for author File: Comments.pdf

Author Response

Please see the point-by-point response in the attachment.

Author Response File: Author Response.docx