(E)-3-((4S,7R,7aR)-3,7-Dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl)-2-methylacrylaldehyde

Base Information

• Chemical Name: (E)-3-((4S,7R,7aR)-3,7-Dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl)-2-methylacrylaldehyde
• CAS No.: 4176-16-3
• Molecular Formula: C15H22 O
• Molecular Weight: 218.339
• Mol file: 4176-16-3.mol

Synonyms:SCHEMBL2167920;SCHEMBL2167927;4,7(11)-Valeradien-12-al;RJZWGDPBGWGJNU-CSKARUKUSA-N;(E)-3-((4S,7R,7aR)-3,7-Dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl)-2-methylacrylaldehyde;Indene-4-acrolein, 2,4,5,6,7,7a-hexahydro-.alpha.,3,7-trimethyl-;2-Propenal, 3-(2,4,5,6,7,7a-hexahydro-3,7-dimethyl-1H-inden-4-yl)-2-methyl-, [4S-[4.alpha.(E),7.beta.,7a.alpha.]]-;2-Propenal, 3-[(4S,7R,7aR)-2,4,5,6,7,7a-hexahydro-3,7-dimethyl-1H-inden-4-yl]-2-methyl-, (2E)-

Chemical Property of (E)-3-((4S,7R,7aR)-3,7-Dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl)-2-methylacrylaldehyde

Chemical Property:

• Vapor Pressure: 0.000222mmHg at 25°C
• Boiling Point: 326°C at 760 mmHg
• Flash Point: 157.9°C
• PSA: 17.07000
• Density: 0.97g/cm³
• LogP: 3.90420
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 218.167065321
• Heavy Atom Count: 16
• Complexity: 348

Purity/Quality:

99% ^*data from raw suppliers

VALENERAL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): A poison.
• Hazard Codes: A poison.

MSDS Files:

Useful:

• Canonical SMILES: CC1CCC(C2=C(CCC12)C)C=C(C)C=O
• Isomeric SMILES: CC1CCC(C2=C(CCC12)C)/C=C(\C)/C=O

Technology Process of (E)-3-((4S,7R,7aR)-3,7-Dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl)-2-methylacrylaldehyde

There total 31 articles about (E)-3-((4S,7R,7aR)-3,7-Dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl)-2-methylacrylaldehyde 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: 70.0%

Valerenol (101628-22-2) → Valerenal (4176-16-3)

Guidance literature:

With manganese(IV) oxide; In chloroform; for 1h;

Reference yield: 65.0%

9-Epi-α-valerenol (75353-84-3,75353-87-6,75419-66-8,75419-67-9,101628-22-2) → 9-Epi-α-valerenal (4176-16-3,75419-64-6,75442-51-2,75442-52-3,89362-59-4,89362-60-7,89362-61-8)

Guidance literature:

With manganese(IV) oxide; In chloroform; for 1h;

Reference yield:

6-methyl-5,7-octadien-2-one (62416-36-8) → 9-Epi-α-valerenal (4176-16-3,75419-64-6,75442-51-2,75442-52-3,89362-59-4,89362-60-7,89362-61-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 2.) Et₃N / 1.) THF, -78 deg C, 3 h, 2.) room temp., 4 h

2: diethyl ether / 72 h / Ambient temperature

3: liq. NH₃, Ca-granulate / diethyl ether

4: H₂ / prehydr. Pt / diethyl ether

5: LiAlH₄ / diethyl ether / 1 h / 0 °C

6: CrO₃, pyridine / CH₂Cl₂ / 15 h / Ambient temperature

7: 20.8 mg / benzoic acid / toluene / 5 h / Heating

8: (i-Bu)2AlH / diethyl ether; hexane / -10 - 0 °C

9: 65 percent / MnO₂ / CHCl₃ / 1 h

With pyridine; chromium(VI) oxide; manganese(IV) oxide; lithium aluminium tetrahydride; ammonia; hydrogen; diisobutylaluminium hydride; calcium; triethylamine; benzoic acid; platinum; In diethyl ether; hexane; dichloromethane; chloroform; toluene;

upstream raw materials:

Valerenol

6-methyl-5,7-octadien-2-one

(3R,7aR)-3,7-Dimethyl-3-trimethylsilanyloxy-2,3,5,7a-tetrahydro-1H-indene-4-carboxylic acid methyl ester

((4R,7R,7aR)-3,7-Dimethyl-2,4,5,6,7,7a-hexahydro-1H-inden-4-yl)-methanol

Downstream raw materials:

valerenic acid

Refernces

• 1、 Bohlmann, Ferdinand,Lonitz, Michael. "Naturally Occurring Terpene Derivatives, 272. On the Constituents of Zexmenia gnaphaloides and the Synthesis of Valerenane Derivatives". . p. 2410 - 2423. Retrieved 2007/10/02.