11,12-dimethoxy-abieta-6,8,11,13-tetraen-20-oic acid methyl ester | 85514-25-6

分子结构分类

有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质

中文名称

——

中文别名

——

英文名称

11,12-dimethoxy-abieta-6,8,11,13-tetraen-20-oic acid methyl ester

英文别名

methyl (4aR,10aS)-5,6-dimethoxy-1,1-dimethyl-7-propan-2-yl-2,3,4,10a-tetrahydrophenanthrene-4a-carboxylate

11,12-dimethoxy-abieta-6,8,11,13-tetraen-20-oic acid methyl ester化学式

CAS

85514-25-6

化学式

C₂₃H₃₂O₄

mdl

——

分子量

372.505

InChiKey

YSNDSABGXVFRFW-GAJHUEQPSA-N

BEILSTEIN

——

EINECS

——

物化性质

沸点：

468.0±45.0 °C(Predicted)
密度：

1.063±0.06 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

5.7
重原子数：

27
可旋转键数：

5
环数：

3.0
sp3杂化的碳原子比例：

0.61
拓扑面积：

44.8
氢给体数：

0
氢受体数：

4

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
——	(4aR,10aS)-5,6-dihydroxy-7-isopropyl-1,1-dimethyl-1,3,4,9,10,10a-hexahydro-2H-9,4a-(epoxymethano)phenanthren-12-one	——	C₂₀H₂₆O₄	330.424
鼠尾草苦内脂	carnosol	5957-80-2	C₂₀H₂₆O₄	330.424

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	methyl (4aR,10aS)-7-isopropyl-5,6-dimethoxy-1,1-dimethyl-1,3,4,9,10,10a-hexahydrophenanthrene-4a(2H)-carboxylate	106096-35-9	C₂₃H₃₄O₄	374.521
——	Carnosinsaeure-dimethylaether	20337-29-5	C₂₂H₃₂O₄	360.494
7-异丙基-5,6-二甲氧基-1,1-二甲基-1,2,3,4,9,10-六氢菲-9-羧酸	5,6-dimethoxy-1,1-dimethyl-7-propan-2-yl-3,4,9,10-tetrahydro-2H-phenanthrene-9-carboxylic acid	182306-50-9	C₂₂H₃₀O₄	358.478
(4aR,9R,10R,10aS)-1,3,4,9,10,10a-六氢-5,6,10-三羟基-1,1-二甲基-7-(1-甲基乙基)-2H-9,4a-(环氧甲烷)菲-12-酮	isorosmanol	93780-80-4	C₂₀H₂₆O₅	346.423
——	((4aR,10aS)-7-isopropyl-5,6-dimethoxy-1,1-dimethyl-1,3,4,9,10,10a-hexahydrophenanthren-4a(2H)-yl)methanol	88515-77-9	C₂₂H₃₄O₃	346.51
——	8-Isopropyl-6,7-dimethoxy-1,1-dimethyl-2,3,4,5,10,11-hexahydro-1H-dibenzo[a,d]cycloheptene	88515-79-1	C₂₂H₃₂O₂	328.495

反应信息

作为反应物：

描述：

11,12-dimethoxy-abieta-6,8,11,13-tetraen-20-oic acid methyl ester 在 potassium tert-butylate 、三溴化硼作用下，以二氯甲烷、二甲基亚砜为溶剂，反应 4.17h，生成次丹参醌

参考文献：

名称：

Rearrangement of methyl 11,12-di-O-methyl-6,7-didehydrocarnosate in basic medium. Easy hemisynthesis of miltirone

摘要：

Methyl 11,12-di-O-methyl-6,7-didehydrocarnosate 3, obtained from the abundant natural product carnosol 1, undergoes an interesting rearrangement when treated with potassium tert-butoxide in dimethyl sulfoxide to give 11,12-dimethoxy-20(10-->7)abeo-abieta-5(10),8,11,13-tetraen-20- oic acid 4, in which an additional double bond is formed between C-5 and C-10 and the carboxylic acid group has migrated from C-10 to C-7, Deprotection of the two methyl ether moieties in 4 with BBr3 allows spontaneous air oxidation and decarboxylation of the catechol derivative to give the potent benzodiazepine agonist miltirone 10. The structure of 6 has been unequivocally elucidated by X-ray diffraction analysis and indirect chemical correlation between 4 and 6 has been established.

DOI：

10.1039/p19960002207
作为产物：

描述：

鼠尾草苦内脂、碘甲烷在 potassium carbonate 作用下，以丙酮为溶剂，反应 24.0h，以53%的产率得到11,12-dimethoxy-abieta-6,8,11,13-tetraen-20-oic acid methyl ester

参考文献：

名称：

分离，结构确定，和barbatusol的绝对构型，一个新的生物活性的二萜与重排的松香烷骨架从唇形彩叶石竹

摘要：

分离自Labiate Coleus barbatus Bentham的Barbatusol是一种新的酚二萜，具有重排的abietane骨架。通过从已知的鼠尾草酚中合成巴巴妥索二甲醚来建立绝对构型。Barbatusol具有生物活性。

DOI：

10.1016/s0040-4020(01)88671-3

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文献信息

Oxidative C-Ring Opening of Abietane Diterpenes with Ammonium Cerium(IV) Nitrate

作者：Lucía Andrés、Joaquín Marrero、Javier Luis

DOI：10.1055/s-2007-977418

日期：2007.4

The oxidation reaction of 11,12-di- O-methylcarnosol with ammonium cerium(IV) nitrate (CAN) gave an abietane diterpene with the C-ring opened and a diester function. The structure of this diester was established by spectroscopic analysis and by chemical means. The reaction of 11,12-di- O-dimethylgaldosol with CAN gave a similar result, yielding a δ-lactone which structure was established as 7-hydroxy-11

11,12-二-O-甲基鼠尾草酚与硝酸铵铈(IV) (CAN) 的氧化反应得到C 环打开且具有二酯官能团的松香烷二萜。这种二酯的结构是通过光谱分析和化学方法确定的。11,12-二-O-二甲基galdosol与CAN的反应得到类似的结果，产生δ-内酯，其结构确定为7-羟基-11,12-SECO-8,13-abietadien-12,7:20 ,6β-dilacton-11-oic酸甲酯通过光谱分析和化学手段。这些结果可能有助于加入其他天然产品，如迷迭香酸。
Chemical evidence for the participation of a perepoxide intermediate in the reaction of singlet oxygen with mono-olefins in relationship with the biogenetic pathway to highly oxidized abietane diterpenes

作者：Javier G. Luis、Lucía S. Andrés、Winston Q. Fletcher

DOI：10.1016/0040-4039(94)88195-2

日期：1994.1

Chemical evidence has been obtained in two separate experiments for the participation of a perepoxide intermediate in the reaction of singlet oxygen with mono-olefins. The intramolecular trapping of such an intermediate in the reaction of 6,7-didehydrocarnosic acid derivatives with molecular oxygen in unequivocal singlet oxygen-generating conditions to give rosmanol and isorosmanol derivatives represents

在两个单独的实验中已获得化学证据，证明过氧化物中间体参与单线态氧与单烯烃的反应。在6,7-二氢戊糖酸衍生物与分子氧在明确的单线态氧生成条件下反应生成分子香豆酚和异香豆酚衍生物的过程中，这种中间体的分子内捕集为上述机理提供了确凿的证据。此外，这些化学证据支持了我们先前关于高氧化己二三烯二萜生物遗传途径的假说，其中酶促脱氢和单重态氧似乎起着重要作用。
Inatani, Reiko; Nakatani, Nobuji; Fuwa, Hidetsugu, Agricultural and Biological Chemistry, 1983, vol. 47, # 3, p. 521 - 528

作者：Inatani, Reiko、Nakatani, Nobuji、Fuwa, Hidetsugu

DOI：——

日期：——
Gonzalez, Antonio G.; Rodriguez Carmen M.; Luis, Javier G., Journal of Chemical Research, Miniprint, 1988, # 4, p. 1141 - 1156

作者：Gonzalez, Antonio G.、Rodriguez Carmen M.、Luis, Javier G.

DOI：——

日期：——
Nakatani, Nobuji; Inatani, Reiko, Agricultural and Biological Chemistry, 1983, vol. 47, # 2, p. 353 - 358

作者：Nakatani, Nobuji、Inatani, Reiko

DOI：——

日期：——