(4R,4aR,7aR,12bS)-9-methoxy-1,2,4,4a,5,6-hexahydro-4,12-methanoisothiochromeno[5,4a-b]benzofuran-7(7aH)-one 3,3-dioxide | 1426537-79-2

分子结构分类

有机化合物 - 苯类化合物 - 菲及其衍生物

中文名称

——

中文别名

——

英文名称

(4R,4aR,7aR,12bS)-9-methoxy-1,2,4,4a,5,6-hexahydro-4,12-methanoisothiochromeno[5,4a-b]benzofuran-7(7aH)-one 3,3-dioxide

英文别名

(1S,5R,13R,17R)-10-methoxy-4,4-dioxo-12-oxa-4lambda6-thiapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-trien-14-one；(1S,5R,13R,17R)-10-methoxy-4,4-dioxo-12-oxa-4λ6-thiapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-trien-14-one

(4R,4aR,7aR,12bS)-9-methoxy-1,2,4,4a,5,6-hexahydro-4,12-methanoisothiochromeno[5,4a-b]benzofuran-7(7aH)-one 3,3-dioxide化学式

CAS

1426537-79-2

化学式

C₁₇H₁₈O₅S

mdl

——

分子量

334.393

InChiKey

YAYPKKODQCZGBW-ZPNMRXEQSA-N

BEILSTEIN

——

EINECS

——

物化性质

熔点：

260 °C(Solvent: Chloroform)
沸点：

602.9±55.0 °C(predicted)
密度：

1.48±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

辛醇/水分配系数(LogP)：

1.5
重原子数：

23
可旋转键数：

1
环数：

5.0
sp3杂化的碳原子比例：

0.59
拓扑面积：

78
氢给体数：

0
氢受体数：

5

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
——	(4R,4aR,7aR,12bS)-9-methoxy-1,2,4,4a,5,6-hexahydro-4,12-methanoisothiochromeno[5,4a-b]benzofuran-7(7aH)-one	1426537-78-1	C₁₇H₁₈O₃S	302.394
——	(4R,4aR,7aR,12bS)-9-methoxy-2,4,4a,5,6,7a-hexahydro-1H-spiro[4,12-methanoisothiochromeno[5,4a-b]-benzofuran-7,2′-[1,3]dioxolane]	1426537-77-0	C₁₉H₂₂O₄S	346.447
二氢可待因酮	Hydrocodone	125-29-1	C₁₈H₂₁NO₃	299.37
——	S-(2-((3a′R,3a1′S,9a′S)-5′-methoxy-2′,3a′,3a1′,9a′-tetrahydro-1′H-spiro[[1,3]dioxolane-2,3′-phenanthro[4,5-bcd]furan]-3a1′-yl)-ethyl) ethanethioate	1426537-75-8	C₂₁H₂₄O₅S	388.485
——	(-)-dihydrocodeinone ethyleneketal	10093-66-0	C₂₀H₂₅NO₄	343.423
——	2-((3a′R,3a1′S,9a′S)-5′-methoxy-2′,3a′,3a1′,9a′-tetrahydro-1′H-spiro[[1,3]dioxolane-2,3′-phenanthro[4,5-bcd]furan]-3a1′-yl)-ethanethiol	1426537-76-9	C₁₉H₂₂O₄S	346.447
——	2-((3a′R,3a1′S,9a′S)-5′-methoxy-2′,3a′,3a1′,9a′-tetrahydro-1′H-spiro[[1,3]dioxolane-2,3′-phenanthro[4,5-bcd]furan]-3a1′-yl)-acetaldehyde	1426537-71-4	C₁₉H₂₀O₅	328.365
——	2-((3a′R,3a1′S,9a′S)-5′-methoxy-2′,3a′,3a1′,9a′-tetrahydro-1′H-spiro[[1,3]dioxolane-2,3′-phenanthro[4,5-bcd]furan]-3a1′-yl)-N,N-dimethylethanamine oxide	1426537-70-3	C₂₁H₂₇NO₅	373.449
——	2-((3a′R,3a1′S,9a′S)-5′-methoxy-2′,3a′,3a1′,9a′-tetrahydro-1′H-spiro[[1,3]dioxolane-2,3′-phenanthro[4,5-bcd]furan]-3a1′-yl)-N,N-dimethylethanamine	1426537-69-0	C₂₁H₂₇NO₄	357.45
——	2-((3a′R,3a1′S,9a′S)-5′-methoxy-2′,3a′,3a1′,9a′-tetrahydro-1′H-spiro[[1,3]dioxolane-2,3′-phenanthro[4,5-bcd]furan]-3a1′-yl)ethyl 4-methylbenzenesulfonate	1426537-74-7	C₂₆H₂₈O₇S	484.57

反应信息

作为产物：

描述：

二氢可待因酮在吡啶、盐酸、 sodium tetrahydroborate 、 sodium periodate 、三甲基氯硅烷、水、双氧水、 sodium methylate 、三氟乙酸酐、 sodium hydroxide 作用下，以四氢呋喃、甲醇、乙醇、二氯甲烷、水、苯为溶剂，反应 177.5h，生成 (4R,4aR,7aR,12bS)-9-methoxy-1,2,4,4a,5,6-hexahydro-4,12-methanoisothiochromeno[5,4a-b]benzofuran-7(7aH)-one 3,3-dioxide

参考文献：

名称：

Heteroatom Analogues of Hydrocodone: Synthesis and Biological Activity

摘要：

Heteroatom analogues of hydrocodone, in which the N-methyl functionality was replaced with oxygen, sulfur, sulfoxide, and sulfone, were prepared by a short sequence from the ethylene glycol ketal of hydrocodone; a carbocyclic analogue of bisnorhydrocodone was also prepared. The compounds were tested for receptor binding and revealed moderate levels of activity for the sulfone analogue of hydrocodone.

DOI：

10.1021/jo3026753

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文献信息

Heteroatom Analogues of Hydrocodone: Synthesis and Biological Activity

作者：Robert D. Giacometti、Jan Duchek、Lukas Werner、Afeef S. Husni、Christopher R. McCurdy、Stephen J. Cutler、D. Phillip Cox、Tomas Hudlicky

DOI：10.1021/jo3026753

日期：2013.4.5

Heteroatom analogues of hydrocodone, in which the N-methyl functionality was replaced with oxygen, sulfur, sulfoxide, and sulfone, were prepared by a short sequence from the ethylene glycol ketal of hydrocodone; a carbocyclic analogue of bisnorhydrocodone was also prepared. The compounds were tested for receptor binding and revealed moderate levels of activity for the sulfone analogue of hydrocodone.