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22128-43-4Relevant academic research and scientific papers
Preparation method of tertiary alcohol compounds
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Paragraph 0045-0047, (2017/03/18)
The invention discloses a preparation method of tertiary alcohol compounds. The method comprises the following steps of (1) enabling a Grignard reagent to be in contact with a reaction substrate as shown in a formula 2 so as to initiate a reaction; and (2) continuously adding the reaction substrate as show in the formula 2 and the Grignard reagent, so that the tertiary alcohol compounds as shown in a formula 1 are generated, (as shown in the description), wherein R1 and R2 are separately C1-C4 straight chain saturated hydrocarbon radicals or unsaturated hydrocarbon radicals. The method provided by the invention is simple to operate, a Grignard reaction process can be effectively controlled, and high-purity and high-yield target products can be obtained, so that high safety in an industrial production process is realized.
Zinc Amide Catalyzed Regioselective Allenylation and Propargylation of Ketones with Allenyl Boronate
Yamashita, Yasuhiro,Cui, Yi,Xie, Peizhong,Kobayashi, Shu
supporting information, p. 6042 - 6045 (2016/01/09)
Zinc amide catalyzed, regioselective allenylation and propargylation of ketones with allenyl boronate is reported. Tertiary allenyl and homopropargyl alcohols were obtained, respectively, in high selectivities, from the same starting materials, simply by changing the reaction conditions. The substrate scope was wide. Mechanistic studies suggest that the reactions are controlled under kinetic and thermodynamic conditions.
A new synthesis of γ-butyrolactones via AuCl3- or Hg(II)-catalyzed intramolecular hydroalkoxylation of 4-bromo-3-yn-1-ols
Reddy, Maddi Sridhar,Kumar, Yalla Kiran,Thirupathi, Nuligonda
scheme or table, p. 824 - 827 (2012/04/05)
An efficient conversion of 4-bromo-3-yn-1-ols to γ-butyrolactones via AuCl3-catalyzed electrophilic cyclization (hydroxyl-assisted regioselective hydration) in wet toluene is described. Various secondary and tertiary alcohols including benzylic systems were found to be equally reactive with moderate to excellent yields obtained in all cases.
Synthesis of 2-normisoprostol, methyl6-(3-hydroxy-2-((E)-4-hydroxy-4- methyloct-1-enyl)-5-oxocyclopentyl)hexanoate
Harikrishna,Mohan, H. Rama,Dubey,Subbaraju, Gottumukkala V.
experimental part, p. 2763 - 2775 (2009/12/06)
Synthesis of 2-normisoprostol, methyl 6-(3-hydroxy-2-((E)-4-hydroxy-4- methyloct-1-enyl)-5-oxocyclopentyl)hexanoate (3), employing two-component coupling strategy based on 1,4-addition followed by DDQ-mediated triethyl silyl deprotection is reported. Desired key intermediates, methyl 6-(3-triethyl silyloxy-5-oxocyclopent-1-enyl)hexanoate (4) and (E)-1-(tributylstannyl)-4- methyloct-1-en-4-yloxy)triethylsilane (5), were prepared from commercially available cycloheptanone and propargyl bromide, and the intermediates were coupled to obtain 3 in a convergent approach.
B-allenyl- and B-(γ-trimethylsilylpropargyl)-10-phenyl-9- borabicyclo[3.3.2]decanes: Asymmetric synthesis of propargyl and α-allenyl 3°-carbinols from ketones
Hernandez, Eliud,Burgos, Carlos H.,Alicea, Eyleen,Soderquist, John A.
, p. 4089 - 4091 (2007/10/03)
Simple and efficient Grignard procedures are reported for the syntheses of B-allenyl-10-(phenyl)-9-borabicyclo[3.3.2]decane (1) and its B-(γ-trimethylsilylpropargyl) counterpart (2) in both enantiomeric forms. Both add selectively to ketones, providing propargyl- and α-silylallenyl 3°-carbinols, respectively (i.e., 6 (61-93% ee) and 9 (64-98% ee)). The air-stable boron byproduct is efficiently recovered and recycled back to either 1 or 2. The ozonolysis and bromination of 9 provide nonracemic α-hydroxy acids and γ-bromopropynyl carbinols, respectively.
Preparation of 15-deoxy-16-hydroxyprostaglandins
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, (2008/06/13)
Analogues of PGE1 having the structural formula, STR1 in which J is R-hydroxymethylene or S-hydroxymethylene; R1 is hydrogen; R2 is hydrogen or together with R4 is a methylene chain of 2 to 3 carbon atoms such that a cycloalkyl of 5 to 6 carbon atoms inclusive is formed; R3 is hydrogen or methyl, or together with R4 is a methylene or a lower alkylated methylene chain of 2 to 5 carbon atoms such that a cycloalkyl or a lower alkylated cycloalkyl of 4 to 7 carbon atoms inclusive is formed, or together with R4 is bicycloalkyl or bicycloalkenyl moiety having the formula: STR2 SUCH THAT A BICYCLOALKYL OR BICYCLOALKENYL COMPOUND IS FORMED, WHEREIN M AND N ARE INTEGERS HAVING A VALUE FROM 0 TO 3, P IS AN INTEGER HAVING A VALUE FROM 0 TO 4 AND Q IS AN INTEGER HAVING A VALUE OF FROM 1 TO 4 AND WHEREIN THE DOUBLE BOND OF SUCH BICYCLOALKENYL IS IN THE M, N, P, OR Q BRIDGE; R4 is hydrogen or methyl or together with R2 or R3 forms a cycloalkyl or bicycloalkyl or bicycloalkenyl as defined above, or together with R5 is a methylene chain of 3 to 5 carbon atoms such that a cycloalkyl of 4 to 6 carbon atoms inclusive is formed; R5 is selected from the group consisting of hydrogen, straight-chain alkyl having from 1 to 3 carbon atoms or together with R4 forms a cycloalkyl as defined above; and R6 is hydrogen or straight-chain alkyl having from 1 to 3 carbon atoms are disclosed. Pge1 ester analogues of the above formula, limited to the structures wherein two of R2, R3 R4 and R5 form a cycloalkyl, lower alkylated cycloalkyl, bicycloalkyl or bicycloalkenyl are also disclosed. The prostaglandin analogues selectively produce bronchodilation and decrease gastric secretion in vivo. Methods of preparing the analogues and starting materials required in the synthesis of the analogues are also disclosed.
