GB1390214A - Cyanoborohydrides - Google Patents
CyanoborohydridesInfo
- Publication number
- GB1390214A GB1390214A GB5383672A GB5383672A GB1390214A GB 1390214 A GB1390214 A GB 1390214A GB 5383672 A GB5383672 A GB 5383672A GB 5383672 A GB5383672 A GB 5383672A GB 1390214 A GB1390214 A GB 1390214A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydroxy
- borane
- compounds
- prepared
- examples
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- -1 Cyanoborohydrides Chemical class 0.000 title abstract 5
- 239000002253 acid Substances 0.000 abstract 3
- 150000007513 acids Chemical class 0.000 abstract 3
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 229910052744 lithium Inorganic materials 0.000 abstract 2
- 229910052700 potassium Inorganic materials 0.000 abstract 2
- 229910052708 sodium Inorganic materials 0.000 abstract 2
- CENMEJUYOOMFFZ-UHFFFAOYSA-N 1,3,2-benzodioxaborole Chemical compound C1=CC=C2OBOC2=C1 CENMEJUYOOMFFZ-UHFFFAOYSA-N 0.000 abstract 1
- MFBVDSCXPZKARI-UHFFFAOYSA-N 7-[3-hydroxy-2-(hydroxymethyl)-5-oxocyclopenten-1-yl]heptanoic acid Chemical compound OC1C(=C(C(C1)=O)CCCCCCC(=O)O)CO MFBVDSCXPZKARI-UHFFFAOYSA-N 0.000 abstract 1
- AMKGKYQBASDDJB-UHFFFAOYSA-N 9$l^{2}-borabicyclo[3.3.1]nonane Chemical compound C1CCC2CCCC1[B]2 AMKGKYQBASDDJB-UHFFFAOYSA-N 0.000 abstract 1
- QAQBKOAJCUHTBD-UHFFFAOYSA-N B1CCCCBCCCC1 Chemical compound B1CCCCBCCCC1 QAQBKOAJCUHTBD-UHFFFAOYSA-N 0.000 abstract 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 abstract 1
- KKNDODAIVSOOPW-UHFFFAOYSA-N CC(C(C)C1=CC=CC=C1)BC(C(C)C1=CC=CC=C1)C Chemical compound CC(C(C)C1=CC=CC=C1)BC(C(C)C1=CC=CC=C1)C KKNDODAIVSOOPW-UHFFFAOYSA-N 0.000 abstract 1
- HVNLBNMOQAPVEH-UHFFFAOYSA-N CC1CC2C(C2CC1BC1C(CC2C(C2C1)(C)C)C)(C)C Chemical compound CC1CC2C(C2CC1BC1C(CC2C(C2C1)(C)C)C)(C)C HVNLBNMOQAPVEH-UHFFFAOYSA-N 0.000 abstract 1
- HFZGNHPKIVYGCH-UHFFFAOYSA-N FC(C(C(C)BC(C)C(C)C(F)(F)F)C)(F)F Chemical compound FC(C(C(C)BC(C)C(C)C(F)(F)F)C)(F)F HFZGNHPKIVYGCH-UHFFFAOYSA-N 0.000 abstract 1
- 150000001299 aldehydes Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 229910000085 borane Inorganic materials 0.000 abstract 1
- 229910052796 boron Inorganic materials 0.000 abstract 1
- 229910052792 caesium Inorganic materials 0.000 abstract 1
- 229910052791 calcium Inorganic materials 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- HXJFQNUWPUICNY-UHFFFAOYSA-N disiamylborane Chemical compound CC(C)C(C)BC(C)C(C)C HXJFQNUWPUICNY-UHFFFAOYSA-N 0.000 abstract 1
- 229910052738 indium Inorganic materials 0.000 abstract 1
- 229910052749 magnesium Inorganic materials 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 229910052751 metal Inorganic materials 0.000 abstract 1
- 229910021645 metal ion Inorganic materials 0.000 abstract 1
- ZCYXXKJEDCHMGH-UHFFFAOYSA-N nonane Chemical compound CCCC[CH]CCCC ZCYXXKJEDCHMGH-UHFFFAOYSA-N 0.000 abstract 1
- BKIMMITUMNQMOS-UHFFFAOYSA-N normal nonane Natural products CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 abstract 1
- 229940094443 oxytocics prostaglandins Drugs 0.000 abstract 1
- 150000003180 prostaglandins Chemical class 0.000 abstract 1
- 125000001453 quaternary ammonium group Chemical group 0.000 abstract 1
- 229910052701 rubidium Inorganic materials 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 229910052712 strontium Inorganic materials 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C405/00—Compounds containing a five-membered ring having two side-chains in ortho position to each other, and having oxygen atoms directly attached to the ring in ortho position to one of the side-chains, one side-chain containing, not directly attached to the ring, a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, and the other side-chain having oxygen atoms attached in gamma-position to the ring, e.g. prostaglandins ; Analogues or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J21/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having an oxygen-containing hetero ring spiro-condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J21/001—Lactones
- C07J21/003—Lactones at position 17
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
Abstract
1390214 Diorgano-cyanoborohydrides G D SEARLE & CO 21 Nov 1972 25 Sept 1972] 53836/72 Headings C2B C2C and C2U Compounds of the general formula where R<SP>1</SP> and R<SP>11</SP> are each an alkyl, cycloalkyl or aralkyl radical which may be substituted (especially by -CF 3 or ..CCl 3 ) or R<SP>1</SP> and R<SP>11</SP> are combined to form a divalent alkylene radical which, together with the boron atom, forms a ring, or are combined so that the group represents a 1,3,2-benzodioxaborolyl or 1,6- diborecanyl group and M<SP>+</SP> is a metal ion selected from Li, Na, K, Rb, Cs, Mg, Ca, Sr, Ba, Al or In or is a fully substituted quaternary ammonium ion, are prepared by reacting a borane R<SP>1</SP>R<SP>11</SP>BH with M+CN- or with M+H and HCN, usually under an inert atmosphere and in a solvent such as THF. In examples, compounds of Formula (I) are prepared from dithexylborane; ( Œ) and (+) and ( - )-diisopinocampheylboranes; disiamylborane; bis-(3-trifluoromethyl - 2 - butyl)borane; di(1 methyl - 2- phenylpropyl)borane; di - (3,7,7 - trimethylbicyclo(4,1,0)hept - 4 - yl)borane; 2,6 - dimethyl - 4 - boralicyclo(3,3,1)nonane; 1,3,2- benzodioxaborole; 9 - borabicyclo(3,3, 1 )nonane; and 1,6-diboracyclodecane, the metal being Na, Li or K. The compounds are used as reducing agents for kelo and aldehyde functional groups, especially in the product of prostaglandins. In Examples, various dl-dihydroxy-9-oxoprost-13- trans - enoic acids and hydroxy- and dihydroxytrans-dienoic acids are prepared by such reduction. In Examples 19 and 25, the reaction is allowed to proceed to give various dl-trihydroxyprost - 13 - trans - enoic acids. In Example 27, 3-hydroxy-2-hydroxymethyl-5- oxo - 1 - cyclopentene - 1 - heptanoic acid is obtained from the corresponding 2-formyl-3- hydroxy-5-oxo compound. In Example 28, 3#,17 - hydroxy - 17α - pregn - 4 - ene - 21 - carboxylic acid y-lactone is obtained from the corresponding 17-hydroxy-3-oxo derivative.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5383672A GB1390214A (en) | 1972-11-21 | 1972-11-21 | Cyanoborohydrides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5383672A GB1390214A (en) | 1972-11-21 | 1972-11-21 | Cyanoborohydrides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1390214A true GB1390214A (en) | 1975-04-09 |
Family
ID=10469140
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5383672A Expired GB1390214A (en) | 1972-11-21 | 1972-11-21 | Cyanoborohydrides |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1390214A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102241698A (en) * | 2011-05-23 | 2011-11-16 | 中国科学院理化技术研究所 | Star-shaped triaryl borane compound and preparation method and application thereof |
-
1972
- 1972-11-21 GB GB5383672A patent/GB1390214A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102241698A (en) * | 2011-05-23 | 2011-11-16 | 中国科学院理化技术研究所 | Star-shaped triaryl borane compound and preparation method and application thereof |
| CN102241698B (en) * | 2011-05-23 | 2013-12-25 | 中国科学院理化技术研究所 | Star-shaped triaryl borane compound and preparation method and application thereof |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |