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(3S,8S,9S,10R,13S,14S,17S)-10,13-dimethyl-17-(2-methyl-1,3-dioxolan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol | 2415-36-3

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

(3S,8S,9S,10R,13S,14S,17S)-10,13-dimethyl-17-(2-methyl-1,3-dioxolan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol

英文别名

(3S,8S,9S,10R,13S,14S,17S)-10,13-dimethyl-17-(2-methyl-1,3-dioxolan-2-yl)-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol

(3S,8S,9S,10R,13S,14S,17S)-10,13-dimethyl-17-(2-methyl-1,3-dioxolan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol化学式

CAS

2415-36-3

化学式

C₂₃H₃₆O₃

mdl

——

分子量

360.537

InChiKey

SPFIKHYEPDYDPC-CPDXTSBQSA-N

BEILSTEIN

——

EINECS

——

物化性质

熔点：

164-167 °C
沸点：

467.8±45.0 °C(Predicted)
密度：

1.12±0.1 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

4.6
重原子数：

26
可旋转键数：

1
环数：

5.0
sp3杂化的碳原子比例：

0.91
拓扑面积：

38.7
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
——	3β-acetylpregn-5-ene	40148-10-5	C₂₅H₃₈O₄	402.574
——	20,20-ethanediyldioxy-5β-pregnane-3α,6α-diol	19316-10-0	C₂₃H₃₈O₄	378.552
孕烯醇酮醋酸酯	Pregnenolone acetate	1778-02-5	C₂₃H₃₄O₃	358.521
孕烯醇酮	Pregnenolone	145-13-1	C₂₁H₃₂O₂	316.484

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	(3S,8S,9S,10R,13S,14S,17S)-3,10,13-trimethyl-17-(2-methyl-1,3-dioxolan-2-yl)-1,2,4,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-ol	1427208-29-4	C₂₄H₃₈O₃	374.564
——	2-((3S,8S,9S,10R,13S,14S,17S)-3-(methoxymethoxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-methyl-1,3-dioxolane	——	C₂₅H₄₀O₄	404.59
——	4-pregnen-3β-ol-20-one ethyleneacetal	95565-58-5	C₂₃H₃₆O₃	360.537
——	20,20-Aethylendioxy-5-pregnen-1α,3β-diol	54021-72-6	C₂₃H₃₆O₄	376.536
——	3β-acetoxy-20,20-ethanediyldioxy-4,4-dimethyl-pregn-5-ene	115759-81-4	C₂₇H₄₂O₄	430.628
——	pregn-5-ene-3,20-dione cyclic 20-(1,2-ethanediylacetal)	1427208-28-3	C₂₃H₃₄O₃	358.521
黄体酮环20-(乙烯缩醛)	20-ethylenedioxy-4-pregnen-3-one	978-98-3	C₂₃H₃₄O₃	358.521
——	20,20-ethanediyldioxy-4,4-dimethyl-pregn-5-en-3-one	102291-09-8	C₂₅H₃₈O₃	386.575
——	20,20-ethanediyldioxy-5β-pregn-2-ene-3-carbonitrile	95839-34-2	C₂₄H₃₅NO₂	369.547
——	(3S,8S,9S,10R,13S,14S,17S)-17-(1-hydroxyethyl)-3,10,13-trimethyl-1,2,4,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-ol	1427208-27-2	C₂₂H₃₆O₂	332.527
——	(4S,5S,8R,9S,10R,13S,14S,17S)-4,10,13-Trimethyl-17-(2-methyl-[1,3]dioxolan-2-yl)-hexadecahydro-cyclopenta[a]phenanthren-3-ol	146201-24-3	C₂₄H₄₀O₃	376.58
——	4α-methyl-3β-hydroxy-5α-pregnan-20-one ethylene ketal	148552-72-1	C₂₄H₄₀O₃	376.58
——	20,20-Aethylendioxy-1,4,6-pregnatrien-3-on	75678-19-2	C₂₃H₃₀O₃	354.489
——	4α-methyl-5α-pregnan-20-one ethylene ketal	146201-26-5	C₂₄H₄₀O₂	360.58
——	20,20-ethanediyldioxy-3ξ-hydroxy-5β-pregnane-3ξ-carbonitrile	95975-17-0	C₂₄H₃₇NO₃	387.563
——	20,20-(ethylenedioxy)-5β-pregnan-3-one	——	C₂₃H₃₆O₃	360.537
——	3β-acetoxy-4,4-dimethyl-pregn-5-en-20-one	115211-23-9	C₂₅H₃₈O₃	386.575
——	4α-methyl-5α-pregnane-3,20-dione 20-ethylene ketal	146201-23-2	C₂₄H₃₈O₃	374.564
——	[(1S)-1-[(3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-3,10,13-trimethyl-1,2,4,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]ethyl] benzoate	1427208-25-0	C₂₉H₄₀O₃	436.635
——	[(1R)-1-[(3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-3,10,13-trimethyl-1,2,4,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]ethyl] benzoate	1427208-26-1	C₂₉H₄₀O₃	436.635
——	1α,3β-Dihydroxy-5-pregnen-20-on	64180-15-0	C₂₁H₃₂O₃	332.483
——	3β-hydroxy-4,4-dimethyl-pregn-5-en-20-one	82340-32-7	C₂₃H₃₆O₂	344.538
——	4-((phenylthio)methyl)-4-pregnene-3,20-dione 20-ethylene ketal	146201-22-1	C₃₀H₄₀O₃S	480.712
——	20,20-Aethylendioxy-1α,2α-epoxy-4,6-pregnadien-3-on	75678-20-5	C₂₃H₃₀O₄	370.489
——	1-[(3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-3,10,13-trimethyl-1,2,4,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]ethanone	19897-94-0	C₂₂H₃₄O₂	330.511
——	4α-methyl-3β-hydroxy-5α-pregnan-20-one ethylene ketal phenyl thiocarbonate	148552-73-2	C₃₁H₄₄O₄S	512.754
——	Thiocarbonic acid O-phenyl ester O-[(4S,5S,8R,9S,10R,13S,14S,17S)-4,10,13-trimethyl-17-(2-methyl-[1,3]dioxolan-2-yl)-hexadecahydro-cyclopenta[a]phenanthren-3-yl] ester	146201-25-4	C₃₁H₄₄O₄S	512.754
4-孕烯-3beta-ol-20-酮	3β-hydroxy-pregn-4-en-20-one	566-66-5	C₂₁H₃₂O₂	316.484

反应信息

作为反应物：

描述：

(3S,8S,9S,10R,13S,14S,17S)-10,13-dimethyl-17-(2-methyl-1,3-dioxolan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol 在 N-甲基-4-哌啶酮、 aluminum isopropoxide 作用下，以78%的产率得到黄体酮环20-(乙烯缩醛)

参考文献：

名称：

5α-地甾烷的C-23和C-24非对映异构体的合成

摘要：

制备C 30生物标记物5α-地甾烷（1）的C-23和C-24非对映异构体的立体选择路线涉及（20S）-20-（碘甲基）-4α-甲基-5α-孕烯（7）与3,4-二甲基戊酸甲酯饱和酯（9）结合，然后还原，主要得到赤型-非对映异构体或7，与α，β-不饱和酯3,4-二甲基戊烯酸甲酯烷基化（12）），然后还原，主要得到苏-非对映异构体。

DOI：

10.1016/0040-4039(93)88018-e
作为产物：

描述：

20,20-ethanediyldioxy-3α,6α-bis-(toluene-4-sulfonyloxy)-5β-pregnane 在水、 potassium acetate 、 N,N-二甲基甲酰胺作用下，生成 (3S,8S,9S,10R,13S,14S,17S)-10,13-dimethyl-17-(2-methyl-1,3-dioxolan-2-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol

参考文献：

名称：

肝去氧胆酸转化为黄体酮

摘要：

开发了 3α,6α-二羟基类固醇向其 3β-羟基-Δ5 类似物的新转化，并将其应用于从猪去氧胆酸制备孕酮。

DOI：

10.1139/v56-130

点击查看最新优质反应信息

文献信息

3BÉTA-(BENZYLOXY)-17ALPHA-METHYL-PREGN-5-EN-20-ONE FOR USE IN THE TREATMENT OF COGNITIVE DISORDERS

申请人：Aelis Farma

公开号：EP3669876A1

公开（公告）日：2020-06-24

The present invention generally relates to a specific pregnenolone derivative for its use for the treatment of a cognitive disorders. More particularly, the invention relates to a compound of Formula (I) for its use in the treatment of cognitive disorders. Indeed, the compound of the invention is in vivo very potent in correcting the cognitive impairments observed in cognitive disorders.

本发明一般涉及一种特定的孕酮衍生物，用于治疗认知障碍。更具体地，本发明涉及一种式（I）的化合物用于治疗认知障碍。事实上，本发明的化合物在体内非常有效地纠正认知障碍中观察到的认知损伤。
Eine ergiebige Herstellung von 1α,3β-Dihydroxy-Δ<sup>5</sup>-steroiden durch Reduktion von 1α,2α-Epoxy-4,6-dien-3-onen mit Lithium in Ammoniak

作者：Andor Fürst、Ludvik Labler、Werner Meier

DOI：10.1002/hlca.19810640621

日期：1981.9.23

An Efficient Procedure for Preparing 1α,3β-Dihydroxy-Δ5-steroids by Reduction of 1α,2α-Epoxy-4,6-dien-3-ones with Lithium in Ammonia

用于制备1α，3β二羟基Δ的有效程序5个由1α还原，-steroids2α环氧-4,6-二烯-3-酮与锂在氨
[EN] COMPOUNDS FOR TREATING CNS DISORDERS<br/>[FR] COMPOSÉS POUR LE TRAITEMENT DE TROUBLES DU SYSTÈME NERVEUX CENTRAL

申请人：SAGE THERAPEUTICS INC

公开号：WO2020264512A1

公开（公告）日：2020-12-30

Provided herein in part is a compound of Formula (I): or a pharmaceutically acceptable salt thereof, pharmaceutical compositions comprising a compound of Formula I, and methods of using the compounds, e.g, in the treatment of CNS- related disorders.

以下部分提供了化合物Formula (I)的结构，或其药用盐，包括含有Formula I化合物的药物组合物，以及使用这些化合物的方法，例如用于治疗与中枢神经系统相关的疾病。
Photoinduced Carboborative Ring Contraction Enables Regio- and Stereoselective Synthesis of Multiply Substituted Five-Membered Carbocycles and Heterocycles

作者：Shengfei Jin、Vu T. Nguyen、Hang T. Dang、Dat P. Nguyen、Hadi D. Arman、Oleg V. Larionov

DOI：10.1021/jacs.7b07128

日期：2017.8.23

herein a photoinduced carboborative ring contraction of monounsaturated six-membered carbocycles and heterocycles. The reaction produces substituted five-membered ring systems stereoselectively and on preparative scales. The products feature multiple stereocenters, including contiguous quaternary carbons. We show that the reaction can serve as a synthetic platform for ring system alteration of natural products

我们在此报告了单不饱和六元碳环和杂环的光诱导碳环收缩。该反应立体选择性地以制备规模产生取代的五元环系统。该产品具有多个立体中心，包括连续的季碳。我们表明该反应可以作为天然产物环系改变的合成平台。该反应也可用于天然产物合成。通过一系列光诱导碳硼酸环收缩、Rauhut-Currier 反应和腈水解酶催化水解的序列，已经实现了蒿甲酸的简明全合成。通过将中间体有机硼烷转化为醇、胺和烯烃，进一步证明了该反应的合成效用。
Process for 1.alpha.,3.beta.-dihydroxy-.DELTA..sup.5 -steroids

申请人：Hoffmann-La Roche Inc.

公开号：US04305881A1

公开（公告）日：1981-12-15

A process for the synthesis of 1.alpha.,3.beta.-dihydroxy-.DELTA..sup.5 -steroids from steroids such as 1.alpha.,2.alpha.-epoxy-cholesta-4,6-dien-3-one, which is reacted with lithium in liquid ammonia in the absence of a proton donator and subsequently reduced by repeated alternative additions of a proton donator, said additions being followed in each case by an equivalent amount of lithium. The final product, a 1.alpha.,3.beta.-dihydorxy-.DELTA..sup.5 -steroid, is useful in the synthesis of derivatives of cholecalciferol.

从类固醇合成1.alpha.，3.beTA.-二羟基-.DELTA..sup.5 -类固醇的过程，例如1.alpha.，2.alpha.-环氧胆甾-4,6-二烯-3-酮与液氨中的锂在无质子给体的情况下发生反应，随后通过重复交替添加质子给体来还原，每次添加后都跟着等量的锂。最终产物，1.alpha.，3.beTA.-二羟基-.DELTA..sup.5 -类固醇，在胆钙化醇衍生物的合成中很有用。