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9,10-dihydrolysergic acid methyl ester | 3006-19-7

分子结构分类

有机化合物 - 生物碱及其衍生物 - 麦角林及其衍生物

中文名称

——

中文别名

——

英文名称

9,10-dihydrolysergic acid methyl ester

英文别名

Methyl 9,10-dihydro-D-lysergate；methyl (6aR,9R,10aR)-7-methyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate；(5R,8R,10R)-6-methyl-ergoline-8-carboxylic acid methyl ester；D-dihydrolysergic-I acid methyl ester；dihydrolysergic acid methyl ester；dihydrolisergic acid；6-Methyl-ergoline-8-carboxylic acid methyl ester；methyl (6aR,9R,10aR)-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxylate

9,10-dihydrolysergic acid methyl ester化学式

CAS

3006-19-7；5143-94-2；35470-53-2；77842-02-5；87247-99-2；96648-31-6；96648-32-7

化学式

C₁₇H₂₀N₂O₂

mdl

——

分子量

284.358

InChiKey

OSKZYLPFYNARRX-UXIGCNINSA-N

BEILSTEIN

——

EINECS

——

物化性质

熔点：

112-114 °C
沸点：

453.8±45.0 °C(Predicted)
密度：

1.227±0.06 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

2.2
重原子数：

21
可旋转键数：

2
环数：

4.0
sp3杂化的碳原子比例：

0.47
拓扑面积：

45.3
氢给体数：

1
氢受体数：

3

上下游信息

上游原料

中文名称	英文名称	CAS号	化学式	分子量
9,10-二氢麦角酸	9,10-dihydrolysergic acid	5878-43-3	C₁₆H₁₈N₂O₂	270.331
二氢麦角隐亭	Dihydroergocryptine	25447-66-9	C₃₂H₄₃N₅O₅	577.724
麦角酸	D-lysergic acid	82-58-6	C₁₆H₁₆N₂O₂	268.315

下游产品

中文名称	英文名称	CAS号	化学式	分子量
(8alpha)-6-甲基-麦角灵-8-羧酸甲酯	methyl (5R,8S,10R)-6-methyl-8-ergolinecarboxylate	5143-94-2	C₁₇H₂₀N₂O₂	284.358
——	6-nor-6-n-propyl-9,10-dihydrolysergic acid methyl ester	63719-09-5	C₁₉H₂₄N₂O₂	312.412
——	6-nor-6-n-ethyl-9,10-dihydrolysergic acid methyl ester	30341-94-7	C₁₈H₂₂N₂O₂	298.385
——	6-methyl-8β-methoxycarbonyl-13-tert-butyl-ergoline	157767-03-8	C₂₁H₂₈N₂O₂	340.466
——	6-(2-propenyl)-9,10-dihydrolysergic acid methyl ester	72821-79-5	C₁₉H₂₂N₂O₂	310.396
9,10-二氢麦角酸	9,10-dihydrolysergic acid	5878-43-3	C₁₆H₁₈N₂O₂	270.331
——	methyl (6aR,9R,10aR)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate	30341-92-5	C₁₆H₁₈N₂O₂	270.331
6-(2-丙烯基)二氢麦角酸	(6aR,9R,10aR)-7-allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylic acid	81409-74-7	C₁₈H₂₀N₂O₂	296.369
——	methyl (6aR,9R,10aR)-3-tert-butyl-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxylate	208995-24-8	C₂₁H₂₈N₂O₂	340.466
——	(6aR,9R,10aR)-3-tert-butyl-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxylic acid	157767-23-2	C₂₀H₂₆N₂O₂	326.439
6-甲基麦角灵-8β-甲醇	9,10-dihydrolysergol	18051-16-6	C₁₆H₂₀N₂O	256.348
——	(6-methyl-ergolin-8α-yl)-methanol	51153-15-2	C₁₆H₂₀N₂O	256.348
——	D-6-propyl-8β-hydroxymethylergoline	63719-21-1	C₁₈H₂₄N₂O	284.401
——	(6-ethyl-ergolin-8-yl)-methanol	63719-20-0	C₁₇H₂₂N₂O	270.374
——	6-methyl-8β-hydroxymethyl-13-tert-butyl-ergoline	157767-04-9	C₂₀H₂₈N₂O	312.455
——	[(6aR,9R,10aR)-7-allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-yl]methanol	72821-88-6	C₁₈H₂₂N₂O	282.385
——	2-bromo-6-methyl-ergoline-8β-carboxylic acid methyl ester	68299-81-0	C₁₇H₁₉BrN₂O₂	363.254
——	6-nor-6-(2,2,2-trichloroethoxycarbonyl)-9,10-dihydrolysergic acid methyl ester	80993-64-2	C₁₉H₁₉Cl₃N₂O₄	445.73
——	D-6-methyl-8-acetylergoline-I	1940-05-2	C₁₇H₂₀N₂O	268.359
6,8beta-二甲基麦角灵	festuclavine	569-26-6	C₁₆H₂₀N₂	240.348
——	6-methyl-ergoline-8β-carboxylic acid hydrazide	1752-45-0	C₁₆H₂₀N₄O	284.361
——	methyl (6aR,9R,10aR)-7-methyl-5-methylsulfanyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxylate	69754-03-6	C₁₈H₂₂N₂O₂S	330.451
——	Dihydrolysergamine	1940-12-1	C₁₆H₂₁N₃	255.363
——	6-methyl-8β-(N-ethoxycarbonylmethyl-aminomethyl)-ergoline	95688-31-6	C₂₀H₂₇N₃O₂	341.453
去乙基氨基甲酰卡麦角林	N-<3-(dimethylamino)propyl>-6-(2-propenyl)-ergoline-8β-carboxamide	85329-86-8	C₂₃H₃₂N₄O	380.533
——	methyl (6aR,9R,10aR)-2-tert-butyl-7-methyl-5-methylsulfanyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxylate	157767-01-6	C₂₂H₃₀N₂O₂S	386.558
——	6-methyl-8β-aminomethyl-13-t-butyl-ergoline	157767-05-0	C₂₀H₂₉N₃	311.47
——	(5R,8R,10R)-6-methyl-8-ergolinylmethyl p-toluenesulfonate	58752-31-1	C₂₃H₂₆N₂O₃S	410.537
——	[(6aR,9R,10aR)-5-chloro-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinolin-9-yl]methanol	66835-16-3	C₁₆H₁₉ClN₂O	290.793
——	Toluene-4-sulfonic acid (6aR,9R,10aR)-7-propyl-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinolin-9-ylmethyl ester	79675-18-6	C₂₅H₃₀N₂O₃S	438.591
——	[(6aR,9R,10aR)-7-ethyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinolin-9-yl]methyl 4-methylbenzenesulfonate	74627-23-9	C₂₄H₂₈N₂O₃S	424.564
——	(5R,8R,10R)-2-bromo-6-methyl-8-ergolinemethanol	160730-40-5	C₁₆H₁₉BrN₂O	335.244
——	3-(6-Methylergolin-8β-ylmethyl)oxazolidin-2-one	——	C₁₉H₂₃N₃O₂	325.411
——	1-Demethylmethergoline	——	C₂₄H₂₇N₃O₂	389.497
——	6-methyl-8β-(3-acetyl-thioureidomethyl)-ergoline	86891-56-7	C₁₉H₂₄N₄OS	356.492
——	N-(6-methylergolin-8β-ylmethyl)succinimide	——	C₂₀H₂₃N₃O₂	337.422
——	N-benzoyldihydro-Lysergamine	——	C₂₃H₂₅N₃O	359.471
——	[(6aR,9S,10aR)-3-tert-butyl-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinolin-9-yl]methanamine	157767-21-0	C₂₀H₂₉N₃	311.47
——	6-Methylcabergoline	——	C₂₄H₃₅N₅O₂	425.574
——	6-methyl-8β-benzoylaminomethyl-13-tert-butyl-ergoline	157767-06-1	C₂₇H₃₃N₃O	415.579
——	6-methyl-8β-(3-phenyl-acryloyl)aminomethyl-13-tert-butyl-ergoline	——	C₂₉H₃₅N₃O	441.616
——	(5R,8R,10R)-6-methyl-8-(1,2,4-triazol-4-ylmethyl)ergoline	——	C₁₈H₂₁N₅	307.398
——	(5R,8R,10R)-6-propyl-8-(1,2,4-triazol-4-ylmethyl)ergoline	——	C₂₀H₂₅N₅	335.452
——	FCE 22716	95688-34-9	C₁₉H₂₂N₄O₂	338.409
——	(10R,7aR,11aR)-8-methyl-7a,8,9,10,11,11a-hexahydro-7H-4,6,8-triazabenzo[de]anthracen-10-carboxylic acid methyl ester	359686-01-4	C₁₇H₁₉N₃O₂	297.357
6-甲基麦角灵-8beta-胺	6-methyl-ergolin-8β-ylamine	51898-44-3	C₁₅H₁₉N₃	241.336
——	(5R,8R,10R)-6-methyl-8-(1-pyrazolylmethyl)ergoline	——	C₁₉H₂₂N₄	306.41
——	(5R,8R,10R)-2-chloro-6-methyl-8-ergolinylmethyl p-toluenesulfonate	74627-27-3	C₂₃H₂₅ClN₂O₃S	444.982
——	1-(6-Methylergolin-8β-ylmethyl)imidazole	——	C₁₉H₂₂N₄	306.41
——	(6aR,9R,10aR)-9-(imidazol-1-ylmethyl)-7-propyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline	——	C₂₁H₂₆N₄	334.464
——	6-methyl-8β-(6-chloro-3-pyridazinyl-carbamoyl)-ergoline	——	C₂₀H₂₀ClN₅O	381.865
——	(5R,8R,10R)-6-methyl-8-(1,2,4-triazol-1-ylmethyl)ergoline	105579-47-3	C₁₈H₂₁N₅	307.398
——	[(6aR,9R,10aR)-5-bromo-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinolin-9-yl]methyl 4-methylbenzenesulfonate	74627-26-2	C₂₃H₂₅BrN₂O₃S	489.433
——	1-(6-Methylergolin-8β-ylmethyl)tetrazole	——	C₁₇H₂₀N₆	308.386
——	N-[[(6aR,9S,10aR)-2-tert-butyl-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinolin-9-yl]methyl]-5-bromopyridine-3-carboxamide	——	C₂₆H₃₁BrN₄O	495.462
——	(5R,8R,10R)-6-propyl-8-(1,2,4-triazol-1-ylmethyl)ergoline	——	C₂₀H₂₅N₅	335.452
——	2-Methyl-1-(6-methylergolin-8β-ylmethyl)imidazole	——	C₂₀H₂₄N₄	320.437
——	2-[[(6aR,9R,10aR)-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinolin-9-yl]methyl]isoindole-1,3-dione	160730-51-8	C₂₄H₂₃N₃O₂	385.466
——	2-Ethyl-1-(6-methylergolin-8β-ylmethyl)imidazole	——	C₂₁H₂₆N₄	334.464
——	3,5-Dimethyl-1-(6-methylergolin-8β-ylmethyl)pyrazole	——	C₂₁H₂₆N₄	334.464
——	1-(6-Methylergolin-8β-ylmethyl)-2-propylimidazole	——	C₂₂H₂₈N₄	348.491
——	6-methyl-8β-phthalimidomethyl-13-tert-butyl-ergoline	157767-37-8	C₂₈H₃₁N₃O₂	441.573
——	(5R,8R,10R)-8-(1,2,4-triazol-1-ylmethyl)ergoline	1027079-07-7	C₁₇H₁₉N₅	293.371
——	2-Isopropyl-1-(6-methylergolin-8β-ylmethyl)imidazole	——	C₂₂H₂₈N₄	348.491
——	(5R,8R,10R)-6-methyl-8-(4-phenyl-1-imidazolylmethyl)ergoline	——	C₂₅H₂₆N₄	382.508
——	(6aR,9R,10aR)-7-allyl-N⁹-[3-(dimethylamino)propyl]-N⁴-ethyl-6a,7,8,9,10,10a-hexahydroindolo[4,3-fg]quinoline-4,9(6H)-dicarboxamide	166533-36-4	C₂₆H₃₇N₅O₂	451.612
——	RV39Sdx97G	115219-11-9	C₂₂H₂₆N₄O₂	378.474
——	2-Ethyl-4-methyl-1-(6-methylergolin-8β-ylmethyl)imidazole	——	C₂₂H₂₈N₄	348.491
——	(9R,6aR,10aR)-7-methyl-6a,7,8,9,10,10a-hexahydro-6H-4-oxa-7-azaacephenanthrylene-9-carboxylic acid methyl ester	359686-15-0	C₁₇H₁₉NO₃	285.343
——	1-(6-Methylergolin-8β-ylmethyl)-2-phenylimidazole	——	C₂₅H₂₆N₄	382.508
卡麦角林EP杂质C	(6aR,9R,10aR)-7-allyl-N⁹-[3-(dimethylamino)propyl]-N⁴-ethyl-N⁹-(ethylcarbamoyl)-6a,7,8,9,10,10a-hexahydroindolo[4,3-fg]quinoline-4,9(6H)-dicarboxamide	126554-50-5	C₂₉H₄₂N₆O₃	522.691
——	(9R,6aR,10aR)-7-methyl-6a,7,8,9,10,10a-hexahydro-6H-4-oxa-5,7-diaza-acephenanthrylene-9-carboxylic acid methyl ester	359686-28-5	C₁₆H₁₈N₂O₃	286.331
——	ethyl 5-methyl-1-(6-methylergolin-8β-ylmethyl)-4-imidazolecarboxylate	——	C₂₃H₂₈N₄O₂	392.501
——	ethyl 4-methyl-1-(6-methylergolin-8β-ylmethyl)-5-imidazolecarboxylate	——	C₂₃H₂₈N₄O₂	392.501
——	BAM 1303	——	C₂₅H₂₅BrN₄	461.404
——	(2R,4aR,10bR)-7-hydroxy-4-methyl-6-oxo-1,2,3,4,4a,5,6,10b-octahydrobenz[f]quinoline-2-carboxylic acid methyl ester	359686-05-8	C₁₆H₁₉NO₄	289.331
——	(2R,4aR,10bR)-7-Amino-1,2,3,4,4a,5,6,10b-octahydro-6-oxobenzochinolin-2-carbonsaeuremethylester	65291-20-5	C₁₆H₂₀N₂O₃	288.346
——	(2R,4aR,10bR)-7-ethoxycarbonylmethyloxy-4-methyl-6-oxo-1,2,3,4,4a,5,6,10b-octahydrobenz[f]quinoline-2-carboxylic acid methyl ester	359686-10-5	C₂₀H₂₅NO₆	375.422
——	(2R,4aR,10bR)-7-Formylamino-1,2,3,4,4a,5,6,10b-octahydro-6-oxobenzochinolin-2-carbonsaeuremethylester	81149-13-5	C₁₇H₂₀N₂O₄	316.357

反应信息

作为反应物：

描述：

9,10-dihydrolysergic acid methyl ester 在 lithium aluminium tetrahydride 、乙醚作用下，生成 6-甲基麦角灵-8β-甲醇

参考文献：

名称：

Zur Kenntnis der Triterpene。140. Mitteilung。弗雷德林斯大学

摘要：

1.达芬斯C 30 H 50 O（I）左旋弗里德伦丁C 29 H 44 O 2（II）乙氧基（IV）-乙酸酯在Eisessiglösungdas-Friedelen-disäure-中的Wasserstoffperoxyd酸酐C 29 H 44 O 3（III），微熔剂zu einemgesättigten，四环酮Keton C 25 H 42 O（VI），阿布巴特·乌尔德（abgebaut wurde）。

DOI：

10.1002/hlca.19490320413
作为产物：

描述：

麦角酸在盐酸、溶剂黄146 、铂作用下，生成 9,10-dihydrolysergic acid methyl ester

参考文献：

名称：

Jacobs; Craig, Journal of Biological Chemistry, 1936, vol. 115, p. 227,237

摘要：

DOI：

点击查看最新优质反应信息

文献信息

Oxydation von Lysergsäure-Derivaten in 2,3-Stellung. 47. Mitteilung über Mutterkornalkaloide

作者：F. Troxler、A. Hofmann

DOI：10.1002/hlca.19590420321

日期：——

entsprechenden Dioxindol-Verbindungen oxydiert. Diese liessen sich mit Zinkstaub in Essigsäure zu Oxindol-Derivaten reduzieren. 2-0xo-2,3-dihydro-d-lysergsäure-diäthylamid, ein biologisches Oxydationsprodukt von d-Lysergsäure-diathylamid, konnte auf diesem Wege in reiner, kristallisierter Form gewonnen werden.

用次氯酸钙溶液氧化各种麦角酸衍生物，得到相应的二氧吲哚化合物。这些可以在乙酸中与锌粉一起还原为羟吲哚衍生物。以此方式，可以得到纯的结晶形式的2-0xo-2，3-二氢-d-麦角酰二乙酰胺，d-麦角酰二乙酰胺的生物氧化产物。
Synthesis and Structure-Activity Relationships of New (5R,8R,10R)-Ergoline Derivatives with Antihypertensive or Dopaminergic Activity.

作者：Sachio OHNO、Yuko ADACHI、Masayuki KOUMORI、Kiyoshi MIZUKOSHI、Mitsuaki NAGASAKA、Kenji ICHIHARA、Ei-ichi KATO

DOI：10.1248/cpb.42.1463

日期：——

containing nitrogen atoms to afford the new ergolines. (5R,8R,10R)-8-(1,2,4-Triazol-1-ylmethyl)-6-methylergoline (4s, maleate: BAM-1110) exhibited potent dopaminergic activity, about 18-fold greater than that of bromocriptine mesylate. (5R,8R,10R)-8-(1,2,4-Triazol-1-ylmethyl)-6-propylergoline (8b, fumarate: BAM-1602) showed extremely potent dopaminergic activity, being about 220 and 1.15 times more active

合成了一系列新的（5R，8R，10R）-麦角灵衍生物，并在有意识的自发性高血压大鼠和单侧6-羟基多巴胺诱导的黑质病变大鼠中测试了它们的降压和多巴胺能活性。由相应的麦角灵羧酸酯制备的（5R，8R，10R）-6-烷基-8-麦角灵甲醇被转化为甲苯磺酸酯，然后用各种含氮原子的五元杂环进行处理，得到新的麦角灵。（5R，8R，10R）-8-（1,2,4-三唑-1-基甲基）-6-甲基麦角灵（4s，马来酸酯：BAM-1110）表现出强力的多巴胺能活性，比溴隐亭高约18倍甲磺酸酯（5R，8R，10R）-8-（1,2,4-三唑-1-基甲基）-6-丙基麦角灵（8b，富马酸酯：BAM-1602）显示出极强的多巴胺能活性，约为220和1。活性分别比溴隐亭甲磺酸盐和甲磺酸培高利特高15倍。几种化合物表现出有效的抗高血压活性。讨论了抗高血压和多巴胺能活动的构效关系。
The Quest for New Mild and Selective Modifications of Natural Structures: Laccase-Catalysed Oxidation of Ergot Alkaloids Leads to Unexpected Stereoselective C-4 Hydroxylation

作者：Cosimo Chirivì、Gabriele Fontana、Daniela Monti、Gianluca Ottolina、Sergio Riva、Bruno Danieli

DOI：10.1002/chem.201201076

日期：2012.8.13

Laccase‐catalysed oxidation of ergot alkaloids in the absence of chemical mediators allowed the unexpected isolation of the mono‐hydroxylated derivatives of compounds 2–7. Structure determination by NMR techniques clearly indicated that hydroxylation took place at the C‐4 benzylic position. Quite notably, the proposed protocol allowed, for the first time, functionalisation at the C‐4 position of the

在不存在化学介质的麦角生物碱的漆酶催化的氧化允许化合物的单羟基化衍生物的意外分离2 - 7。NMR技术确定的结构清楚地表明羟基化发生在C-4苄基位置。值得注意的是，拟议的协议首次允许在麦角灵骨架的C-4位置进行功能化。取决于是否存在C-10α-甲氧基取代基，羟基化反应是立体选择性的（提供C-4αOH衍生物）或生成2：1比率的C-4α/C-4βOH混合物，分别。
Electrochemical Oxidation of Ergolines

作者：Karlheinz Seifert、Nguyen Minh Phuong、Beverly R. Vincent

DOI：10.1002/hlca.19920750125

日期：1992.2.5

An electrochemical procedure for the preparation of D-3-alkoxy-halogen-2,3-dihydro-6-methyl-2-oxoergolines-I is described.

描述了制备D-3-烷氧基-卤素-2，3-二氢-6-甲基-2-氧代麦角灵-1的电化学方法。
Synthesis and antihypertensive activity of 2,4-dioxoimidazolidin-1-yl and perhydro-2,4-dioxopyrimidin-1-yl ergoline derivatives

作者：Sergio Mantegani、Enzo Brambilla、Carla Caccia、Laura Chiodini、Daniela Ruggieri、Ernesto Lamberti、Enrico Di Salle、Patricia Salvati

DOI：10.1016/s0014-827x(98)00023-8

日期：1998.4

The synthesis and antihypertensive activity of a series of 2,4-dioxoimidazolidin-1-yl and perhydro-2,4-dioxopyrimidin-1-yl ergoline derivatives are reported. The oral antihypertensive activity was studied in spontaneously hypertensive rats (SHRs) by measuring systolic blood pressure by an indirect tail-cuff method at different times after treatment. The prolactin lowering activity (indirectly measured

报道了一系列2,4-二氧杂咪唑啉-1-基和过氢-2,4-二氧嘧啶亚基-1-基麦角灵衍生物的合成和降压活性。通过在治疗后的不同时间通过间接尾袖法测量收缩压来研究自发性高血压大鼠（SHRs）的口服降压活性。还研究了大鼠的催乳激素降低活性（通过硝化试验间接测定）和小鼠的口服急性毒性。这项研究的结果表明，有效的降压麦角灵衍生物没有与多巴胺能刺激有关的副作用，而且δ9,10双键对于在这些化合物中赋予高效力具有重要意义。