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(1S,2S,3R,4R)-2-乙酰氧基甲基-3-羟甲基-7-氧杂双环[2.2.1]庚-5-烯 | 142507-54-8

分子结构分类

有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物

中文名称

(1S,2S,3R,4R)-2-乙酰氧基甲基-3-羟甲基-7-氧杂双环[2.2.1]庚-5-烯

中文别名

——

英文名称

(1S,2S,3R,4R)-2-acetoxymethyl-3-hydroxymethyl-7-oxabicyclo[2.2.1]hept-5-ene

英文别名

(+)-7-oxabicyclo[2.2.1]hept-5-ene-exo-2,exo-3-dimethanol monoacetate；[(1S,2S,3R,4R)-3-(hydroxymethyl)-7-oxabicyclo[2.2.1]hept-5-en-2-yl]methyl acetate

(1S,2S,3R,4R)-2-乙酰氧基甲基-3-羟甲基-7-氧杂双环[2.2.1]庚-5-烯化学式

CAS

142507-54-8

化学式

C₁₀H₁₄O₄

mdl

——

分子量

198.219

InChiKey

SHMZQHPZATWAJG-JLIMGVALSA-N

BEILSTEIN

——

EINECS

——

物化性质

熔点：

49-51 °C
沸点：

292.9±30.0 °C(Predicted)
密度：

1.196±0.06 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

-0.1
重原子数：

14
可旋转键数：

4
环数：

2.0
sp3杂化的碳原子比例：

0.7
拓扑面积：

55.8
氢给体数：

1
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
——	exo-cis-2,3-bis(acetoxymethyl)-7-oxabicyclo[2.2.1]hept-5-ene	142438-51-5	C₁₂H₁₆O₅	240.256
——	exo-2,3-bis(hydroxymethyl)-7-oxabicyclo[2.2.1]hept-5-ene	817201-06-2	C₈H₁₂O₃	156.181
——	exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride	6118-51-0	C₈H₆O₄	166.133

下游产品

中文名称	英文名称	CAS号	化学式	分子量
(1S,2S,3R,4R)-2-乙酰氧基甲基-3-(1-乙氧基乙氧基)甲基-7-氧杂双环[2.2.1]庚-5-烯	(1S,2S,3R,4R)-2-acetoxymethyl-3-(1-ethoxyethoxy)methyl-7-oxabicyclo[2.2.1]hept-5-ene	817201-07-3	C₁₄H₂₂O₅	270.326
——	(1R,2R,3S,4S,1'S,3'R)-2-(1',3'-dihydroxybutyl)-3-acetoxymethyl-7-oxabicyclo[2.2.1]-5-hepten	200883-83-6	C₁₃H₂₀O₅	256.299
——	(1R,2S,3S,4S)-2-formyl-3-acetoxymethyl-7-oxabicyclo[2.2.1]-5-hepten	200883-79-0	C₁₀H₁₂O₄	196.203
(1R,2R,3S,4S)-2-(1-乙氧基乙氧基)甲基-3-羟甲基-7-氧杂双环[2.2.1]庚-5-烯	(1R,2R,3S,4S)-2-(1-ethoxyethoxy)methyl-3-hydroxymethyl-7-oxabicyclo[2.2.1]hept-5-ene	817201-08-4	C₁₂H₂₀O₄	228.288
——	(1S,2S,3S,4R)-2-hydroxymethyl-3-methyl-7-oxabicyclo[2.2.1]hept-5-ene	817201-22-2	C₈H₁₂O₂	140.182
——	(1R,2S,3S,4S,1'S)-2-(1'-hydroxy-3'-oxobutyl)-3-acetoxymethyl-7-oxabicyclo[2.2.1]-5-hepten	200883-81-4	C₁₃H₁₈O₅	254.283
——	(1S,2S,3R,4R)-2-acetoxymethyl-3-diisopropylsilanyloxymethyl-7-oxa-bicyclo[2.2.1]hept-5-en-2-ene	1127304-24-8	C₁₆H₂₈O₄Si	312.481
——	Acetic acid (1S,2S,3R,4R)-3-(tert-butyl-dimethyl-silanyloxymethyl)-7-oxa-bicyclo[2.2.1]hept-5-en-2-ylmethyl ester	198822-19-4	C₁₆H₂₈O₄Si	312.481
——	(1R,2R,3S,4S,6'S,4'R)-2-(1',3'-dioxa-2',2',4'-trimethylcyclohexyl)-3-acetoxymethyl-7-oxabicyclo[2.2.1]-5-hepten	200883-84-7	C₁₆H₂₄O₅	296.364
——	(1S,2R,6R,7R)-4,10-dioxatricyclo[5.2.1.02,6]dec-8-en-3-one	104485-85-0	C₈H₈O₃	152.15
——	(1R,2S,6S,7S)-4,10-Dioxa-tricyclo[5.2.1.0^2,6]dec-8-en-3-one	——	C₈H₈O₃	152.15
——	(1R,6S,7S,8R)-7-hydroxymethyl-8-methyl-9-oxabicyclo[4.2.1]nona-2,4-diene	817201-01-7	C₁₀H₁₄O₂	166.22
——	(1R,2R,3S,4S,6'S,4'R)-2-(1',3'-dioxa-2',2',4'-trimethylcyclohexyl)-3-hydroxymethyl-7-oxabicyclo[2.2.1]-5-hepten	200883-86-9	C₁₄H₂₂O₄	254.326
——	(1S,2S,3R,4R,1'R,3'S)-2-(4',6'-dioxa-5',5'-dimethyl-3'-propylcyclohexyl)-3-hydroxymethyl-7-oxabicyclo[2.2.1]hept-5-ene	198822-25-2	C₁₆H₂₆O₄	282.38
——	methyl (2S)-2-[(1S,2R,3S,5S,6R,7R)-5-[(2R)-2-hydroxypropyl]-4,10-dioxatricyclo[5.2.1.02,6]dec-8-en-3-yl]propanoate	200883-90-5	C₁₅H₂₂O₅	282.337
——	methyl (2R)-2-[(1S,2R,3S,5S,6R,7R)-5-[(2R)-2-hydroxypropyl]-4,10-dioxatricyclo[5.2.1.02,6]dec-8-en-3-yl]propanoate	200883-91-6	C₁₅H₂₂O₅	282.337
——	[(1S,2S,3R,4R)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl]-methanol	198822-20-7	C₁₄H₂₆O₃Si	270.444
——	(1R,2R,3S,4R,6'S,4'R)-2-(1',3'-dioxa-2',2',4'-trimethylcyclohexyl)-3-formyl-7-oxabicyclo[2.2.1]-5-hepten	200883-87-0	C₁₄H₂₀O₄	252.31
——	(1S,2S,3S,4R,1'R,3'S)-2-(4',6'-dioxa-5',5'-dimethyl-3'-propylcyclohexyl)-3-formyl-7-oxabicyclo[2.2.1]hept-5-ene	198822-26-3	C₁₆H₂₄O₄	280.364
——	(1R,6S,7S,8S)-7-[1-hydroxy-1-(5-oxo-2-hydro-2-furyl)methyl]-8-methyl-9-oxabicyclo[4.2.1]nona-2,4-diene	817201-40-4	C₁₄H₁₆O₄	248.279
——	(1R,6S,7R,8S)-8-methyl-9-oxabicyclo[4.2.1]nona-2,4-diene-7-carboxylic acid	817201-45-9	C₁₀H₁₂O₃	180.203
——	(+)-mycoepoxydiene	221898-91-5	C₁₆H₁₈O₅	290.316
——	(1R,3S)-1-[(1S,2S,3R,4R)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-7-oxa-bicyclo[2.2.1]hept-5-en-2-yl]-hexane-1,3-diol	198822-23-0	C₁₉H₃₆O₄Si	356.578
——	(1S,2R,3R,4R)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]-7-oxabicyclo[2.2.1]hept-5-ene-2-carbaldehyde	198822-21-8	C₁₄H₂₄O₃Si	268.428
——	(1R)-1-[(1S,2S,3R,4R)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]-7-oxabicyclo[2.2.1]hept-5-en-2-yl]-1-hydroxyhexan-3-one	198822-22-9	C₁₉H₃₄O₄Si	354.562
——	((1R,2R,3S,4S)-3-Hydroxymethyl-7-oxa-bicyclo[2.2.1]hept-5-en-2-ylmethyl)-carbamic acid tert-butyl ester	178206-86-5	C₁₃H₂₁NO₄	255.314
——	(1R,6S,7R,8S)-7-[(2S,3S)-3-acetoxy-6-hydroxy-3,6-dihydro-2H-pyran-2-yl]-8-methyl-9-oxabicyclo[4.2.1]nona-2,4-diene	817201-37-9	C₁₆H₂₀O₅	292.332
——	tert-Butyl-[(1R,2R,3S,4S)-3-((4R,6S)-2,2-dimethyl-6-propyl-[1,3]dioxan-4-yl)-7-oxa-bicyclo[2.2.1]hept-5-en-2-ylmethoxy]-dimethyl-silane	198822-24-1	C₂₂H₄₀O₄Si	396.643

反应信息

作为反应物：

描述：

(1S,2S,3R,4R)-2-乙酰氧基甲基-3-羟甲基-7-氧杂双环[2.2.1]庚-5-烯在盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺吡啶、咪唑、 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 lead(IV) acetate 、盐酸、叔丁基过氧化氢、 4-二甲氨基吡啶、 manganese(IV) oxide 、 sodium chlorite 、 sodium tetrahydroborate 、 disodium hydrogenphosphate 、四氧化锇、正丁基锂、 cerium(III) chloride 、 bis(acetylacetonate)oxovanadium 、偶氮二异丁腈、十二/十四烷基二甲基氧化胺、氨基磺酸、 potassium tert-butylate 、四丁基氟化铵、水、溴、三正丁基氢锡、 sodium methylate 、 4-甲基苯磺酸吡啶、 L-Selectride 、 sodium hydride 、 1-羟基苯并三唑、戴斯-马丁氧化剂、溶剂黄146 、三乙胺、 sodium iodide 作用下，以四氢呋喃、甲醇、异辛烷、乙醚、正己烷、二氯甲烷、水、 N,N-二甲基甲酰胺、丙酮、甲苯、丁酮、叔丁醇、苯为溶剂，反应 140.08h，生成 4-epi-mycoepoxydiene

参考文献：

名称：

（+）-Mycoepoxydiene和相关天然产物（-）-1893A的不对称总合成：一锅开环/交叉/环闭合复分解在构建其9-氧杂双环[4.2.1] nona-2,4中的应用-二烯骨架

摘要：

（+）-mycoepoxydiene和（-）-1893A的总合成已完成。本合成策略的特点是使用一锅式开环/交叉易位（ROM / CM），然后进行闭环易位（RCM）反应，从而简化了9-氧杂双环[4.2.1] nona的构建由7-氧杂双环[2.2.1]庚-2-烯衍生物和1,3-丁二烯形成的-2,4-二烯构架。通过将糠醇氧化重排成吡喃酮，将顺序复分解产物转化为（+）-Mycoepoxydiene。从而建立了其绝对立体化学。从共同的中间体，还通过乙烯基醇醛醇醛醇缩合反应合成了结构上相关的天然产物（-）-1893A。

DOI：

10.1021/jo048566j
作为产物：

描述：

exo-2,3-bis(hydroxymethyl)-7-oxabicyclo[2.2.1]hept-5-ene 在吡啶、 Lipase PS (Amano) 、水作用下，以四氢呋喃为溶剂，反应 497.0h，生成 (1S,2S,3R,4R)-2-乙酰氧基甲基-3-羟甲基-7-氧杂双环[2.2.1]庚-5-烯

参考文献：

名称：

（+）-Mycoepoxydiene和相关天然产物（-）-1893A的不对称总合成：一锅开环/交叉/环闭合复分解在构建其9-氧杂双环[4.2.1] nona-2,4中的应用-二烯骨架

摘要：

（+）-mycoepoxydiene和（-）-1893A的总合成已完成。本合成策略的特点是使用一锅式开环/交叉易位（ROM / CM），然后进行闭环易位（RCM）反应，从而简化了9-氧杂双环[4.2.1] nona的构建由7-氧杂双环[2.2.1]庚-2-烯衍生物和1,3-丁二烯形成的-2,4-二烯构架。通过将糠醇氧化重排成吡喃酮，将顺序复分解产物转化为（+）-Mycoepoxydiene。从而建立了其绝对立体化学。从共同的中间体，还通过乙烯基醇醛醇醛醇缩合反应合成了结构上相关的天然产物（-）-1893A。

DOI：

10.1021/jo048566j

点击查看最新优质反应信息

文献信息

Synthesis of Natural-Product-Like Molecules with Over Eighty Distinct Scaffolds

作者：Daniel Morton、Stuart Leach、Christopher Cordier、Stuart Warriner、Adam Nelson

DOI：10.1002/anie.200804486

日期：2009.1

Seeking scaffold diversity: A synthetic approach for the combinatorial variation of the scaffolds of small molecules is described. Using just six basic reaction types, compounds with 84 distinct scaffolds were prepared. The compounds had many natural‐product‐like structural features including rich stereochemistry, heterocyclic and unsaturated ring systems, and dense functionalization.

寻求支架多样性：描述了小分子支架组合变异的合成方法。仅使用六种基本反应类型，就制备了具有 84 种不同支架的化合物。这些化合物具有许多类似于天然产物的结构特征，包括丰富的立体化学、杂环和不饱和环系统以及密集的官能化。
A novel synthesis of 2,5-dihydropyrrole derivatives as enantiomerically enriched building blocks

作者：Christophe Cinquin、Michel Bortolussi、Robert Bloch

DOI：10.1016/0040-4020(96)00323-7

日期：1996.5

A general synthesis of optically active 2,5-dihydropyrroles (3-pyrrolines) substituted at the 2-position by a functionalized chain is described. A highly stereoselective intramolecular Michael reaction afforded the five-membered nitrogen rings with an excellent enantiomeric purity. The unsaturation was generated by a retro Diels-Alder reaction.

描述了在2位被官能化的链取代的旋光的2,5-二氢吡咯（3-吡咯啉）的一般合成。高度立体选择性的分子内迈克尔反应提供了具有优异对映体纯度的五元氮环。不饱和是通过逆狄尔斯-阿尔德反应产生的。
A general and stereoselective approach to nonactate esters and isomers: A versatile synthesis of (+)-methyl nonactate

作者：Gérard Mandville、Christian Girard、Robert Bloch

DOI：10.1016/s0040-4020(97)10118-1

日期：1997.12

A total synthesis of (+)-methyl nonactate from a chiral synthon obtained by enantioselective enzymatic transesterification is described. This new approach involves stereoselective reactions of aldolisation, reduction and intramolecular Michael addition and appears to be quite general since it could be applied as well to the synthesis of both enantiomers of 2- or 8-epi nonactate esters or homologues

描述了通过对映选择性酶促酯交换反应从手性合成子中合成（+）-甲基非乙酸酯的全过程。该新方法涉及醛醇缩合，还原和分子内迈克尔加成的立体选择性反应，并且由于可以同时用于2-或8-表位非乳酸酯或同系物的对映异构体的合成而显得十分普遍。
Asensio, Gregorio; Andreu, Cecilia; Marco, J. Alberto, Chemische Berichte, 1992, vol. 125, # 10, p. 2233 - 2238

作者：Asensio, Gregorio、Andreu, Cecilia、Marco, J. Alberto

DOI：——

日期：——
A novel and efficient stereoselective synthesis of the southern part of pamamycin-607

作者：Gérard Mandville、Christian Girard、Robert Bloch

DOI：10.1016/s0957-4166(97)00475-8

日期：1997.11

The C1'C11' portion of the antibiotic pamamycin-607 Was synthesized from the enantiomerically pure hydroxy acetate 3, readily available by enzymatic transesterification of the corresponding diol with vinylacetate. This synthesis entailed a series of stereoselective transformations: the absolute configurations of C-6' and C-8' were fixed by an aldol condensation followed by an anti-reduction of the resulting beta-hydroxyketone. The configurations of the last two asymmetric centers C-2' and C-3' were controlled by a novel highly diastereoselective intramolecular cyclization catalyzed by fluoride ions. (C) 1997 Elsevier Science Ltd.