JPS62174089A - 有機ゲルマニウム化合物 - Google Patents
有機ゲルマニウム化合物Info
- Publication number
- JPS62174089A JPS62174089A JP61313544A JP31354486A JPS62174089A JP S62174089 A JPS62174089 A JP S62174089A JP 61313544 A JP61313544 A JP 61313544A JP 31354486 A JP31354486 A JP 31354486A JP S62174089 A JPS62174089 A JP S62174089A
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- halogen
- group
- compounds
- 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.)
- Granted
Links
- 150000002291 germanium compounds Chemical class 0.000 title claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 18
- 125000005843 halogen group Chemical group 0.000 claims abstract description 14
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 10
- 125000003277 amino group Chemical group 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 102
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract description 20
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 12
- 229910021529 ammonia Inorganic materials 0.000 abstract description 10
- 150000001252 acrylic acid derivatives Chemical class 0.000 abstract description 9
- 239000002904 solvent Substances 0.000 abstract description 7
- 229910052736 halogen Inorganic materials 0.000 abstract description 5
- 239000002253 acid Substances 0.000 abstract description 4
- 238000007259 addition reaction Methods 0.000 abstract description 2
- 238000005660 chlorination reaction Methods 0.000 abstract description 2
- 150000002367 halogens Chemical class 0.000 abstract 3
- 239000013543 active substance Substances 0.000 abstract 1
- 239000002246 antineoplastic agent Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 238000000921 elemental analysis Methods 0.000 description 17
- 230000015572 biosynthetic process Effects 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 14
- 238000005481 NMR spectroscopy Methods 0.000 description 13
- 238000004949 mass spectrometry Methods 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 239000013078 crystal Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 229910005742 Ge—C Inorganic materials 0.000 description 10
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 8
- 238000004364 calculation method Methods 0.000 description 8
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 7
- MUDDKLJPADVVKF-UHFFFAOYSA-N trichlorogermane Chemical compound Cl[GeH](Cl)Cl MUDDKLJPADVVKF-UHFFFAOYSA-N 0.000 description 7
- -1 carboxyethyl Chemical group 0.000 description 6
- 229910052732 germanium Inorganic materials 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 6
- 238000001816 cooling Methods 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- 238000002329 infrared spectrum Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 230000001766 physiological effect Effects 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000005292 vacuum distillation Methods 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 150000001793 charged compounds Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 230000003301 hydrolyzing effect Effects 0.000 description 3
- CSCPPACGZOOCGX-MICDWDOJSA-N 1-deuteriopropan-2-one Chemical compound [2H]CC(C)=O CSCPPACGZOOCGX-MICDWDOJSA-N 0.000 description 2
- XRYJTKGEJGVBCC-UHFFFAOYSA-N 2-germylpropanoic acid Chemical compound CC([GeH3])C(O)=O XRYJTKGEJGVBCC-UHFFFAOYSA-N 0.000 description 2
- MIAXGDNPGHKUKI-UHFFFAOYSA-N 2-methyl-3-trichlorogermylbutanoic acid Chemical compound OC(=O)C(C)C(C)[Ge](Cl)(Cl)Cl MIAXGDNPGHKUKI-UHFFFAOYSA-N 0.000 description 2
- FZGJYVHQPCUUDH-UHFFFAOYSA-N 2-methyl-3-trichlorogermylpropanoyl chloride Chemical compound ClC(=O)C(C)C[Ge](Cl)(Cl)Cl FZGJYVHQPCUUDH-UHFFFAOYSA-N 0.000 description 2
- YYPNJNDODFVZLE-UHFFFAOYSA-N 3-methylbut-2-enoic acid Chemical compound CC(C)=CC(O)=O YYPNJNDODFVZLE-UHFFFAOYSA-N 0.000 description 2
- IKHZITMUHDPORA-UHFFFAOYSA-N 3-trichlorogermylbutanoyl chloride Chemical compound Cl[Ge](Cl)(Cl)C(C)CC(Cl)=O IKHZITMUHDPORA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 101150041968 CDC13 gene Proteins 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 229920005654 Sephadex Polymers 0.000 description 2
- 239000012507 Sephadex™ Substances 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical class C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000002523 gelfiltration Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- RJUIDDKTATZJFE-NSCUHMNNSA-N (e)-but-2-enoyl chloride Chemical compound C\C=C\C(Cl)=O RJUIDDKTATZJFE-NSCUHMNNSA-N 0.000 description 1
- IAORDJBFFZZXKB-UHFFFAOYSA-N 2-methyl-3-trichlorogermylbutanoyl chloride Chemical compound ClC(=O)C(C)C(C)[Ge](Cl)(Cl)Cl IAORDJBFFZZXKB-UHFFFAOYSA-N 0.000 description 1
- MUJDREPOQOZYKI-UHFFFAOYSA-N 3-trichlorogermylbutanoic acid Chemical compound Cl[Ge](Cl)(Cl)C(C)CC(O)=O MUJDREPOQOZYKI-UHFFFAOYSA-N 0.000 description 1
- CJBSBAIVMJIWKH-UHFFFAOYSA-L C(C)C(=O)[O-].[Ge+2].C(C)C(=O)[O-] Chemical class C(C)C(=O)[O-].[Ge+2].C(C)C(=O)[O-] CJBSBAIVMJIWKH-UHFFFAOYSA-L 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- LSFGNGLLMQZPFT-UHFFFAOYSA-N NC(=O)CC[Ge] Chemical compound NC(=O)CC[Ge] LSFGNGLLMQZPFT-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- TXHIDIHEXDFONW-UHFFFAOYSA-N benzene;propan-2-one Chemical compound CC(C)=O.C1=CC=CC=C1 TXHIDIHEXDFONW-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 238000004455 differential thermal analysis Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229910000078 germane Inorganic materials 0.000 description 1
- 229940093626 germanium sesquioxide Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000003049 inorganic solvent Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- XEABSBMNTNXEJM-UHFFFAOYSA-N propagermanium Chemical compound OC(=O)CC[Ge](=O)O[Ge](=O)CCC(O)=O XEABSBMNTNXEJM-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000005556 structure-activity relationship Methods 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61313544A JPS62174089A (ja) | 1986-12-25 | 1986-12-25 | 有機ゲルマニウム化合物 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61313544A JPS62174089A (ja) | 1986-12-25 | 1986-12-25 | 有機ゲルマニウム化合物 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58090424A Division JPS59216893A (ja) | 1983-05-23 | 1983-05-23 | 有機ゲルマニウム化合物の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62174089A true JPS62174089A (ja) | 1987-07-30 |
| JPH0521917B2 JPH0521917B2 (enrdf_load_stackoverflow) | 1993-03-25 |
Family
ID=18042598
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61313544A Granted JPS62174089A (ja) | 1986-12-25 | 1986-12-25 | 有機ゲルマニウム化合物 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62174089A (enrdf_load_stackoverflow) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54116100A (en) * | 1978-03-01 | 1979-09-10 | Sato Ryuichi | Production of organic germanium polymer |
| JPS54160319A (en) * | 1978-06-08 | 1979-12-19 | Asai Germanium Res Inst | Manufacture of organic germanium compound |
-
1986
- 1986-12-25 JP JP61313544A patent/JPS62174089A/ja active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54116100A (en) * | 1978-03-01 | 1979-09-10 | Sato Ryuichi | Production of organic germanium polymer |
| JPS54160319A (en) * | 1978-06-08 | 1979-12-19 | Asai Germanium Res Inst | Manufacture of organic germanium compound |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0521917B2 (enrdf_load_stackoverflow) | 1993-03-25 |
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