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(5R)-5-Methyl-2-(phenylsulfinyl)-cyclohexanone, with the CAS number 88154-77-2, is an organic compound characterized by its chiral center at the 5-position and a phenylsulfinyl group at the 2-position. It exists as a gel, indicating its potential for use in various applications due to its physical state.

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  • 88154-77-2 Structure
  • Basic information

    1. Product Name: (5R)-5-Methyl-2-(phenylsulfinyl)-cyclohexanone
    2. Synonyms: (5R)-5-Methyl-2-(phenylsulfinyl)-cyclohexanone;(5R)-5-methyl-2-(phenylsulfinyl)cyclohexan-1-one
    3. CAS NO:88154-77-2
    4. Molecular Formula: C13H16O2S
    5. Molecular Weight: 236
    6. EINECS: N/A
    7. Product Categories: Aromatics;Sulfur & Selenium Compounds
    8. Mol File: 88154-77-2.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: N/A
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: N/A
    6. Refractive Index: N/A
    7. Storage Temp.: N/A
    8. Solubility: Dichloromethane, Ethyl Acetate
    9. CAS DataBase Reference: (5R)-5-Methyl-2-(phenylsulfinyl)-cyclohexanone(CAS DataBase Reference)
    10. NIST Chemistry Reference: (5R)-5-Methyl-2-(phenylsulfinyl)-cyclohexanone(88154-77-2)
    11. EPA Substance Registry System: (5R)-5-Methyl-2-(phenylsulfinyl)-cyclohexanone(88154-77-2)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 88154-77-2(Hazardous Substances Data)

88154-77-2 Usage

Uses

Used in Organic Synthesis:
(5R)-5-Methyl-2-(phenylsulfinyl)-cyclohexanone is used as a key intermediate in organic synthesis for the production of various pharmaceuticals, agrochemicals, and specialty chemicals. Its unique structure allows for selective reactions and transformations, making it a valuable building block in the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (5R)-5-Methyl-2-(phenylsulfinyl)-cyclohexanone is used as a chiral synthon for the development of enantiomerically pure drugs. Its presence of a chiral center and a phenylsulfinyl group provides opportunities for asymmetric synthesis and the creation of novel bioactive compounds with potential therapeutic applications.
Used in Agrochemical Industry:
(5R)-5-Methyl-2-(phenylsulfinyl)-cyclohexanone is also utilized in the agrochemical industry as a precursor for the synthesis of chiral pesticides and other agrochemicals. Its ability to be selectively modified and functionalized makes it an attractive candidate for the development of new and improved agrochemical products.
Used in Specialty Chemicals:
In the specialty chemicals sector, (5R)-5-Methyl-2-(phenylsulfinyl)-cyclohexanone is employed as a versatile building block for the synthesis of chiral compounds with specific applications in various industries, such as fragrances, flavors, and materials science. Its unique properties and reactivity contribute to the creation of high-value specialty chemicals.

Check Digit Verification of cas no

The CAS Registry Mumber 88154-77-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,8,1,5 and 4 respectively; the second part has 2 digits, 7 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 88154-77:
(7*8)+(6*8)+(5*1)+(4*5)+(3*4)+(2*7)+(1*7)=162
162 % 10 = 2
So 88154-77-2 is a valid CAS Registry Number.

88154-77-2Relevant articles and documents

Bioinspired Diversification Approach Toward the Total Synthesis of Lycodine-Type Alkaloids

Haley, Hannah M. S.,Payer, Stefan E.,Papidocha, Sven M.,Clemens, Simon,Nyenhuis, Jonathan,Sarpong, Richmond

supporting information, p. 4732 - 4740 (2021/04/07)

Nitrogen heterocycles (azacycles) are common structural motifs in numerous pharmaceuticals, agrochemicals, and natural products. Many powerful methods have been developed and continue to be advanced for the selective installation and modification of nitrogen heterocycles through C-H functionalization and C-C cleavage approaches, revealing new strategies for the synthesis of targets containing these structural entities. Here, we report the first total syntheses of the lycodine-type Lycopodium alkaloids casuarinine H, lycoplatyrine B, lycoplatyrine A, and lycopladine F as well as the total synthesis of 8,15-dihydrohuperzine A through bioinspired late-stage diversification of a readily accessible common precursor, N-desmethyl-β-obscurine. Key steps in the syntheses include oxidative C-C bond cleavage of a piperidine ring in the core structure of the obscurine intermediate and site-selective C-H borylation of a pyridine nucleus to enable cross-coupling reactions.

A concise asymmetric total synthesis of (+)-fawcettimine

Zeng, Xin,Jia, Zhuqing,Qiu, Fayang G.

supporting information, (2020/09/16)

A straightforward and stereocontrolled total synthesis of (+)-fawcettimine was accomplished from the known (R)-5-methyl-2-cyclohexen-one in 11 steps. The synthesis features a palladium mediated cycloalkenylation of a silyl enol ether for assembling the 6/

Efforts toward the synthesis of (+)-Lyconadin A

Karella, Satish,Raghavan, Sadagopan

, (2020/08/10)

Abstract: Synthetic efforts toward the synthesis of (+)-lyconadin A are described. B-Alkyl Suzuki coupling is utilized for combining 2-iodo cyclohexenone with the piperidine subunit. The piperidine subunit is derived from 5-bromo-3-nicotinic acid, and iod

Protecting-Group-Free Total Synthesis of (-)-Lycopodine via Phosphoric Acid Promoted Alkyne Aza-Prins Cyclization

Ma, Donghui,Zhong, Zhuliang,Liu, Zaimin,Zhang, Mingjie,Xu, Shiyan,Xu, Dengyu,Song, Dengpeng,Xie, Xingang,She, Xuegong

supporting information, p. 4328 - 4331 (2016/11/09)

A protecting-group-free route for the total synthesis of (-)-lycopodine was demonstrated in only 8 steps from Wade's fawcettimine enone (12 steps from commercial availiable (R)-(+)-pulegone). The key core of this alkaloid was constructed through a phosphoric acid promoted and highly stereocontrolled alkyne aza-Prins cyclization reaction, synchronously establishing the bridged B-ring and the C13 quaternary stereocenter. Importantly, the synthesis further features a new efficient approach for the preparation of other lycopodine-type alkaloids.

Total synthesis of (+)-fawcettidine

Kozak, Jennifer A.,Dake, Gregory R.

scheme or table, p. 4221 - 4223 (2009/03/11)

(Chemical Equation Presented) Alkaloids alchemy: A synthesis of the Lycopodium alkaloid (+)-fawcettidine (see structure) has been developed which requires 16 steps from (R)-(+)-pulegone as the chiral starting material. Key steps include a platinum(II)-cat

Synthesis of termini-differentiated 6-carbon stereotetrads: An alkylative oxidation strategy for preparation of the C21-C26 segment of apoptolidin

Chen, Yuzhong,Evarts Jr., Jerry B.,Torres, Eduardo,Fuchs, Philip L.

, p. 3571 - 3574 (2007/10/03)

(graph presented) Two methods have been developed for the synthesis of epoxide 36. The first uses (+)-pulegone 25 as an enantiopure starting material and introduces the requisite intricacy of target 22 in 12 operations. The second method employs an enanti

Photochemical rearrangement of 2-phenylthio-1,3-cyclohexanediols to deoxysugars. Application to a stereospecific synthesis of (+)-cis-rose oxide

Gravel, Denis,Bordeleau, Josee

, p. 8035 - 8038 (2007/10/03)

The present paper reports the stereospecific synthesis of (+)-cis-rose oxide, the unnatural isomer of the fragrant oil isolated from Bulgarian roses and Bourbon geraniums. The synthesis serves to illustrate the potential of a new photochemical rearrangement of carbocycles to deoxysugars reported earlier.

Enantiospecific synthesis of rpr 107880 : A new non peptide substance P antagonist

Mutti, Stephane,Daubie, Christophe,Decalogne, Francois,Fournier, Robert,Rossi, Pierre

, p. 3125 - 3128 (2007/10/03)

The synthesis of enantiomerically pure RPR 107880 is described. The synthetic strategy is based on the use of the readily available and inexpensive (R)-(+)-pulegone. Copyright

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