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3β-Acetoxy-5α-ergosta-7,22-dien-6-on | 2529-97-7

分子结构分类

有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物

中文名称

——

中文别名

——

英文名称

3β-Acetoxy-5α-ergosta-7,22-dien-6-on

英文别名

[(3S,5S,9R,10R,13R,14R,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-6-oxo-1,2,3,4,5,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-yl] acetate

CAS

2529-97-7

化学式

C₃₀H₄₆O₃

mdl

——

分子量

454.693

InChiKey

QNSOCDXXOMBZGN-QLMCZQHPSA-N

BEILSTEIN

——

EINECS

——

物化性质

沸点：

534.3±49.0 °C(Predicted)
密度：

1.04±0.1 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

7.3
重原子数：

33
可旋转键数：

6
环数：

4.0
sp3杂化的碳原子比例：

0.8
拓扑面积：

43.4
氢给体数：

0
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
——	(22E)-5α-hydroxyergosta-7,22-dien-6-on-3β-yl acetate	481-23-2	C₃₀H₄₆O₄	470.693
3,5-二羟基麦角甾醇-7,22-二烯-6-酮	3β,5α-dihydroxy-(22E,24R)-ergosta-7,22-dien-6-one	14858-07-2	C₂₈H₄₄O₃	428.656
——	(22E)-3α,5-cyclo-5α-ergosta-7,22-dien-6-one	3037-46-5	C₂₈H₄₂O	394.641
(3b,22E)-麦角甾-5,7,22-三烯-3b-醇 3-乙酸酯	ergosterol acetate	2418-45-3	C₃₀H₄₆O₂	438.694

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	3β-acetoxy-5α-ergost-7-en-6-one	2623-02-1	C₃₀H₄₈O₃	456.709
——	3β-hydroxy-6-keto-5β-bisnorchol-7-ene aldehyde acetate	57125-27-6	C₂₄H₃₄O₄	386.532
——	3β-hydroxy-6-keto-5α-bisnorchol-7-ene aldehyde acetate	81918-29-8	C₂₄H₃₄O₄	386.532
——	5α-pregn-7-ene-3β-ol-6,20-dione acetate	81918-30-1	C₂₃H₃₂O₄	372.505
——	Acetic acid (3S,9R,10R,13R,14R,17R)-17-((S)-2-acetoxy-5-hydroxy-1,5-dimethyl-hexyl)-10,13-dimethyl-6-oxo-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester	81918-37-8	C₃₁H₄₈O₆	516.719
——	3β,20-dihydroxy-6-keto-5ξ-bisnorchol-7-ene aldehyde 3-acetate	81918-40-3	C₂₄H₃₄O₅	402.531
——	5ξ-cholesta-7,24-diene-3β,22ξ-diol-6-one diacetate	81918-35-6	C₃₁H₄₆O₅	498.703
——	Acetic acid (3S,9R,10R,13S,14R,17S)-10,13-dimethyl-17-((R)-2-methyl-oxiranyl)-6-oxo-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester	81918-38-9	C₂₄H₃₄O₄	386.532
——	(22E,24R)-3β-hydroxy-5α-ergosta-7,22-dien-6-one	24570-81-8	C₂₈H₄₄O₂	412.656
——	Acetic acid (3S,9R,10R,13S,14R,17S)-17-((S)-1-chloro-2-hydroxy-1-methyl-ethyl)-10,13-dimethyl-6-oxo-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester	81918-39-0	C₂₄H₃₅ClO₄	422.993
——	(22R,23R,24R)-2α,3α,22,23-tetrahydroxy-5α-ergost-7-en-6-one	108375-83-3	C₂₈H₄₆O₅	462.67
——	(22S,23S,24R)-2α,3α,22,23-tetrahydroxy-5α-ergost-7-en-6-one	108375-84-4	C₂₈H₄₆O₅	462.67
——	3β-acetoxy-14-hydroxy-5α-ergosta-7,22-dien-6-one	89948-37-8	C₃₀H₄₆O₄	470.693
——	pregn-7-ene-3β,14α-diol-6,20-dione 3-acetate	81918-33-4	C₂₃H₃₂O₅	388.504
——	Acetic acid 1-[(S)-1-((3S,9R,10R,13R,14S,17R)-3-acetoxy-14-hydroxy-10,13-dimethyl-6-oxo-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-ethyl]-4-hydroxy-4-methyl-pentyl ester	82008-62-6	C₃₁H₄₈O₇	532.718
——	3β-acetoxy-5α-ergost-22t-en-6-one	35603-22-6	C₃₀H₄₈O₃	456.709
——	5ξ-cholesta-7,24-diene-3β,20,22-triol-6-one	81918-41-4	C₂₇H₄₂O₄	430.628
——	Acetic acid (3S,9R,10R,13S,14R,17S)-17-[(R)-5-(3-hydroxy-3-methyl-butyl)-2,2,4-trimethyl-[1,3]dioxolan-4-yl]-10,13-dimethyl-6-oxo-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester	81918-43-6	C₃₂H₅₀O₆	530.745
——	(22E,24R)-5α-ergosta-2,7,22-trien-6-one	17131-80-5	C₂₈H₄₂O	394.641
——	(20S)-2β,3β-Diacetoxy-14α-hydroxy-20-formyl-6-oxo-5β-pregn-7-en	17131-88-3	C₂₆H₃₆O₇	460.568
——	Acetic acid (3S,9R,10R,13S,14R,17S)-10,13-dimethyl-6-oxo-17-[(R)-2,2,4-trimethyl-5-(3-methyl-but-2-enyl)-[1,3]dioxolan-4-yl]-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester	81918-42-5	C₃₂H₄₈O₅	512.73
(3S,5R,9R,10R,13R,17R)-17-[(2S,3R)-3,6-二羟基-6-甲基庚烷-2-基]-3,14-二羟基-10,13-二甲基-2,3,4,5,9,11,12,15,16,17-十氢-1H-环戊二烯并[a]菲-6-酮	2-deoxyecdysone	31575-91-4	C₂₇H₄₄O₅	448.643
——	(22R)-2β,3β-Diacetoxy-14α,22,25-trihydroxy-6-oxo-Δ⁷-5β-cholestenin-(23)	17131-90-7	C₃₁H₄₄O₈	544.686
——	Acetic acid (3S,9R,10R,13R,14R,17R)-17-((S)-2-acetoxy-5-hydroxy-1,5-dimethyl-hexyl)-6-hydroxy-10,13-dimethyl-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester	81918-36-7	C₃₁H₅₀O₆	518.734
2-脱氧-20-羟基蜕皮素	2-deoxyecdysterone	17942-08-4	C₂₇H₄₄O₆	464.643
——	Acetic acid (3S,9R,10R,13R,14S,17S)-14-hydroxy-17-[(R)-5-(3-hydroxy-3-methyl-butyl)-2,2,4-trimethyl-[1,3]dioxolan-4-yl]-10,13-dimethyl-6-oxo-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester	81918-44-7	C₃₂H₅₀O₇	546.745
——	(22E,24R)-3β-OTs-5α-ergosta-7,22-dien-6-one	19723-82-1	C₃₅H₅₀O₄S	566.846
——	premixisterone	74396-17-1	C₂₇H₄₄O₅	448.643
——	(22E)-5β-ergosta-7,22-diene-3β,6β-diol	118574-74-6	C₂₈H₄₆O₂	414.672

反应信息

作为反应物：

描述：

3β-Acetoxy-5α-ergosta-7,22-dien-6-on 在 selenium(IV) oxide 、 potassium tert-butylate 、氧气、叔丁醇、三(二甲胺基)膦作用下，以 1,4-二氧六环为溶剂，反应 7.0h，生成 pregn-7-ene-3β,14α-diol-6,20-dione 3-acetate

参考文献：

名称：

Partial synthesis of 2-desoxyecdysone and 2-desoxyecdysterone, insect molting hormones

摘要：

DOI：

10.1007/bf00948241
作为产物：

描述：

3β,6α-Diacetoxy-5α-hydroxy-ergosta-7,22-dien 在对甲苯磺酸作用下，以苯为溶剂，生成 3β-Acetoxy-5α-ergosta-7,22-dien-6-on

参考文献：

名称：

Oxidation of ergosterol acetate with chromic anhydride

摘要：

DOI：

10.1007/bf00564742

点击查看最新优质反应信息

文献信息

Fe(II)-Induced Fragmentation Reaction of ?-Hydroperoxy-?,?-enones. Part 1. Synthesis of 13(14?8)-abeo-Steroids

作者：Luigi Canonica?、Bruno Danieli、Giordano Lesma、Giovanni Palmisano、Angelo Mugnoli

DOI：10.1002/hlca.19870700320

日期：1987.5.6

Some steroidal analogues embodying the hitherto unknown 13(148)-abeo skeleton have been synthesized by Fe(II)-induced rearrangement (tandem β-fission/reductive alkylation) of 14α-hydroperoxy-7-en-6-ones. The configurational assignment was made by thorough analysis of NMR spectra; the structure of one of the products was unambiguously assessed by X-ray single-crystal analysis.

通过Fe（II）诱导的14α-hydroperoxy-7-en-6-one的重排（串联β-裂变/还原烷基化）合成了一些体现迄今未知的13（148）-abeo骨架的甾体类似物。通过对NMR光谱的彻底分析来进行构型分配。通过X射线单晶分析明确评估了其中一种产品的结构。
Discoveries and Challenges en Route to Swinhoeisterol A

作者：Fenja L. Duecker、Robert C. Heinze、Simon Steinhauer、Philipp Heretsch

DOI：10.1002/chem.202001405

日期：2020.8.6

synthetic studies is reported that culminated in the first synthesis of 13(14→8),14(8→7)diabeo‐steroid swinhoeisterol A as well as the related dankasterones A and B, 13(14→8)abeo‐steroids, and periconiastone A, a 13(14→8)abeo‐4,14‐cyclo‐steroid. Experiments are described in detail that provided further insight into the mechanism of the switchable radical framework reconstruction approach. By discussing failed

在这项工作中，报告了作者的合成研究的完整记录，最终首次合成了 13(14→8),14(8→7)di abeo 类固醇 swinhoeisterol A 以及相关的 dankasterones A和B , 13(14→8) abeo ‐类固醇，以及 periconiastone A，一种 13(14→8) abeo ‐4,14-环类固醇。详细描述了实验，进一步深入了解可切换激进框架重建方法的机制。通过讨论针对 swinhoeisterol A 的失败策略和策略，最终提出了成功的路线，该路线也允许获得结构密切相关的类似物，例如 Δ 22 ‐24- epi ‐swinhoeisterol A。
The stereospecificity of carbanion reduction processes

作者：D. H. R. Barton、C. H. Robinson

DOI：10.1039/jr9540003045

日期：——
The synthesis of 23,24-14C-ecdysone

作者：William B. Smith、George P. Newsoroff

DOI：10.1016/0039-128x(73)90055-x

日期：1973.12
905. 3 : 5-cycloErgosta-7 : 22-dien-6β-ol and 3 : 5-cycloergosta-7 : 9(11) : 22-trien-6β-ol

作者：G. H. R. Summers

DOI：10.1039/jr9580004489

日期：——