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17553-86-5

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17553-86-5 Usage

Description

(S)-(+)-2,3,7,7A-TETRAHYDRO-7A-METHYL-1H is a white to beige crystalline powder that serves as an intermediate in the preparation of Indenedione. It is also known as (S)-(+)-Hajos-Parrish diketone and has been utilized in various chemical reactions for the synthesis of complex organic compounds.

Uses

Used in Pharmaceutical Industry:
(S)-(+)-2,3,7,7A-TETRAHYDRO-7A-METHYL-1H is used as an intermediate for the preparation of Indenedione, which is a significant compound in the pharmaceutical industry.
Used in Total Synthesis:
In the field of organic chemistry, (S)-(+)-Hajos-Parrish diketone is used as a reactant in the total synthesis of steroidal alkaloids, such as cortistatins. This application is crucial for the development of novel bioactive compounds with potential pharmaceutical applications.
Used in Stereoselective Preparation:
(S)-(+)-2,3,7,7A-TETRAHYDRO-7A-METHYL-1H is employed in the stereoselective preparation of hydroanthracenol and related polycyclic compounds. This is achieved through Ti(Oi-Pr)4-promoted photoenolization and Diels-Alder reaction, which are essential techniques in organic synthesis for creating complex molecular structures with specific stereochemistry.
Used in Synthesis of Allyldiboron Compounds:
In the field of organometallic chemistry, (S)-(+)-2,3,7,7A-TETRAHYDRO-7A-METHYL-1H is used in the synthesis of γ,γ-disubstituted allyldiboron compounds. This is accomplished by reacting with allylic 1,1-diboronate reagents via Cu-catalyzed borylation and 1,2-addition reaction, which are important for the development of new materials and pharmaceuticals with unique properties.

Check Digit Verification of cas no

The CAS Registry Mumber 17553-86-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,7,5,5 and 3 respectively; the second part has 2 digits, 8 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 17553-86:
(7*1)+(6*7)+(5*5)+(4*5)+(3*3)+(2*8)+(1*6)=125
125 % 10 = 5
So 17553-86-5 is a valid CAS Registry Number.
InChI:InChI=1/C10H12O2/c1-10-5-4-8(11)6-7(10)2-3-9(10)12/h6H,2-5H2,1H3/t10-/m0/s1

17553-86-5 Well-known Company Product Price

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  • Aldrich

  • (664073)  (S)-(+)-2,3,7,7a-Tetrahydro-7a-methyl-1H-indene-1,5(6H)-dione  97%

  • 17553-86-5

  • 664073-1G

  • 833.04CNY

  • Detail

17553-86-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name (S)-(+)-2,3,7,7A-TETRAHYDRO-7A-METHYL-1H

1.2 Other means of identification

Product number -
Other names (S)-(+)-5,6,7,8-Tetrahydro-8-Methylindan-1,5-dione

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:17553-86-5 SDS

17553-86-5Downstream Products

17553-86-5Relevant articles and documents

Grieco et al.

, p. 573 (1976)

β-Homoamino acids as catalysts in enantioselective intra- and intermolecular aldol reactions

Limbach, Michael

, p. 3843 - 3847 (2006)

β3-Homoamino acids catalyze the intra- (cf. the Hajos-Parrish-Eder-Sauer-Wiechert reaction) as well as the intermolecular aldol reaction. The stereochemical outcome with selectivities of up to 83% ee is reversed in the intramolecular reaction,

Protecting-group-free total synthesis of aplykurodinone-1

Tang, Yu,Liu, Ji-Tian,Chen, Ping,Lv, Ming-Can,Wang, Zhen-Zhen,Huang, Yi-Kun

, p. 11729 - 11734 (2014)

A concise, stereoselective, and protecting-group-free total synthesis of aplykurodinone-1 from Hajos-Parrish ketone was described. The synthetic approach features a sequence of aerobic allylic oxidation and elimination of alcohol 9. The key intermediate for this synthesis was formed by a stereoselective intramolecular radical cyclization.

Inotropic activity of hydroindene amidinohydrazones

Sevillano,Melero,Caballero,Tomé,Lelièvre,Geering,Crambert,Carrón,Medarde,San Feliciano

, p. 127 - 136 (2002)

Several hydroindenic derivatives (7a-methyl-2,3,5,6,7,7a-hexahydro-1H-indenes), bearing an amidinohydrazone at C-5 and different moieties at C-1, have been synthesized and evaluated for their inotropic and chronotropic effects on right- and left-guinea-pig-atria activity. Three of them showed the same profile as digoxin, although with lower potency. The effect on Na+,K+ ATPase (NKA) was also evaluated for these three compounds, observing that two of them, with the same absolute configuration as natural cardenolides, are also NKA inhibitors, while the compound with the opposite configuration lacks such an effect. More interestingly, both active compounds act without affecting the cardiac rhythm. This could be related to the selective inhibition of the human α2β1 isozyme (associated with the inotropic effect) with respect to the α1β1 isozyme (associated with the maintenance of basal ionic levels in the cell and the toxic effect of cardenolides).

Construction of key building blocks towards the synthesis of cortistatins

Indu, Satrajit,Kaliappan, Krishna P.,Telore, Rahul D.

supporting information, p. 2432 - 2446 (2020/04/22)

This work reports the construction of key building blocks towards the synthesis of cortistatins; a family of steroidal alkaloids. Cortistatin A, being a primary target due to its superior biological properties over other congeners, has been prepared by two different synthetic routes. Synthesis of the precursor to the heavily substituted A-ring starting from d-glucose and construction of the DE-ring junction employing a Hajos-Parrish ketone as a chiral pool have been demonstrated. Efforts are underway to assemble these key fragments and build towards the total synthesis of cortistatin A.

A Highly Active Polymer-Supported Catalyst for Asymmetric Robinson Annulations in Continuous Flow

Canellas, Santiago,Ayats, Carles,Henseler, Andrea H.,Pericàs, Miquel A.

, p. 1383 - 1391 (2017/08/09)

The preparation through Robinson annulation of enantiopure building blocks with both academic and industrial relevance, such as the Wieland-Miescher and Hajos-Parrish ketones, has suffered from important drawbacks, such as the need for high catalyst loading or extremely long reaction times. Here we report a heterogenized organocatalyst based on Luo's diamine for fast and broad-scope enantioselective Robinson annulation reactions. The polystyrene-supported diamine 19a enables the high-yield, highly enantioselective preparation of a wide range of chiral bicyclic enones under mild conditions, with reaction times as short as 60 min (batch) or residence times of 10 min (flow). In contrast with its homogeneous counterpart 19b, the catalytic resin 19a experiences a notable increase in catalytic activity with temperature in 2-MeTHF (a 10-fold decrease in reaction times without erosion in enantioselectivity is observed from room temperature to 55 °C). The scope of the transformation in batch mode has been illustrated with 14 examples, including examples only reported in poorly enantioenriched (22n) or in racemic form (22k). Enantiopure 22k has been used as the starting material for a straightforward formal synthesis of the antibiotic and antifeedant sesquiterpene (-)-isovelleral (24). The heterogenized catalyst 19a admits extended recycling (10 cycles) and has been used to develop the first asymmetric Robinson annulations in continuous flow. The potential of the flow process is illustrated by the large-scale preparation of the Wieland-Miescher ketone (65 mmol in 24 h of operation, TON of 117) and by a sequential flow experiment leading to a library of eight enantioenriched diketone compounds.

Evolution of a Unified Strategy for Complex Sesterterpenoids: Progress toward Astellatol and the Total Synthesis of (-)-Nitidasin

Hog, Daniel T.,Huber, Florian M. E.,Jiménez-Osés, Gonzalo,Mayer, Peter,Houk, Kendall N.,Trauner, Dirk

supporting information, p. 13646 - 13665 (2015/09/22)

Astellatol and nitidasin belong to a subset of sesterterpenoids that share a sterically encumbered trans-hydrindane motif with an isopropyl substituent. In addition, these natural products feature intriguing polycyclic ring systems, posing significant challenges for chemical synthesis. Herein, the evolution of our stereoselective strategy for isopropyl trans-hydrindane sesterterpenoids is detailed. These endeavors included the synthesis of several building blocks, enabling studies toward all molecules of this terpenoid subclass, and of advanced intermediates of our initial route toward a biomimetic synthesis of astellatol. These findings provided the basis for a second-generation and a third-generation approach toward astellatol that eventually culminated in the enantioselective total synthesis of (-)-nitidasin. In particular, a series of substrate-controlled transformations to install the ten stereogenic centers of the target molecule was orchestrated and the carbocyclic backbone was forged in a convergent fashion. Furthermore, the progress toward the synthesis of astellatol is disclosed and insights into some observed yet unexpected diastereoselectivities by detailed quantum-mechanical calculations are provided. Two and a half molecules: Astellatol and nitidasin are polycyclic sesterterpenoids, posing considerable challenges for synthetic chemists. In this full account, the evolution of a synthetic strategy for these and structurally related natural products is given (see scheme). The presented work includes efforts toward a biomimetic synthesis of astellatol, a successful route for the first total synthesis of (-)-nitidasin, and quantum-mechanical investigations into unexpected diastereosectivities.

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