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2(S)-<(tert-butyldiphenylsilyl)oxy>-4(Z)-decenal | 100428-41-9

分子结构分类

有机化合物 - 有机金属化合物 - 有机类金属化合物

中文名称

——

中文别名

——

英文名称

2(S)-<(tert-butyldiphenylsilyl)oxy>-4(Z)-decenal

英文别名

(Z,2S)-2-[tert-butyl(diphenyl)silyl]oxydec-4-enal

2(S)-<(tert-butyldiphenylsilyl)oxy>-4(Z)-decenal化学式

CAS

100428-41-9

化学式

C₂₆H₃₆O₂Si

mdl

——

分子量

408.656

InChiKey

HMGJNGVQXSRXDG-AGUXYKHFSA-N

BEILSTEIN

——

EINECS

——

物化性质

沸点：

460.3±45.0 °C(Predicted)
密度：

0.99±0.1 g/cm3(Predicted)

计算性质

辛醇/水分配系数(LogP)：

5.66
重原子数：

29.0
可旋转键数：

11.0
环数：

2.0
sp3杂化的碳原子比例：

0.42
拓扑面积：

26.3
氢给体数：

0.0
氢受体数：

2.0

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
——	2S-(t-butyldiphenylsilyloxy)dec-4Z-en-1-ol	131392-94-4	C₂₆H₃₈O₂Si	410.672
——	3-O-(tert-butyldiphenylsilyl)-5(Z)-undecene-1,2(R),3(S)-triol	100333-62-8	C₂₇H₄₀O₃Si	440.698
——	(Z)-(2S,3R)-3-(tert-Butyl-diphenyl-silanyloxy)-undec-5-ene-1,2-diol	100311-69-1	C₂₇H₄₀O₃Si	440.698
——	1-benzoyloxy-2S-(t-butyldiphenylsilyloxy)dec-4Z-ene	131392-93-3	C₃₃H₄₂O₃Si	514.78
——	(2R,3S)-(Z)-3-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-5-undecene-1,2,3-triol	95646-05-2	C₃₀H₄₄O₃Si	480.763
——	tert-Butyl-[(Z)-(R)-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-non-3-enyloxy]-diphenyl-silane	100311-68-0	C₃₀H₄₄O₃Si	480.763
——	2-deoxy-3-O-(tert-butyldiphenylsilyl)-4,5-bis-O-(1-methylethylidene)-D-erythro-pentose	93292-42-3	C₂₄H₃₂O₄Si	412.601
——	(3R)-3-[tert-butyl(diphenyl)silyl]oxy-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]propanal	85593-60-8	C₂₄H₃₂O₄Si	412.601
——	tert-butyl-[(1R)-1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3,3-bis(ethylsulfanyl)propoxy]-diphenylsilane	85593-59-5	C₂₈H₄₂O₃S₂Si	518.857
——	2-deoxy-3-O-(tert-butyldiphenylsilyl)-4,5-O-isopropylidene-D-erythro-pentose diethyl dithioacetal	93292-41-2	C₂₈H₄₂O₃S₂Si	518.857

下游产品

中文名称	英文名称	CAS号	化学式	分子量
——	<(tert-butyldiphenylsilyl)oxy>-2(E),6(Z)-decedienal	100311-74-8	C₂₈H₃₈O₂Si	434.694
——	4(S)-<(tert-butyldiphenylsilyl)oxy>-2(E),6(Z)-dodecadienyl-1-ol	218162-93-7	C₂₈H₄₀O₂Si	436.71
——	(3S)-(1E,5Z)-3-O-((tert-butyldiphenylsilyl)oxy)-1-iodo-1,5-undecadiene	164932-95-0	C₂₇H₃₇IOSi	532.58
——	(S,5Z,10E,14Z)-12-((tert-butyldiphenylsilyl)oxy)icosa-5,8,10,14-tetraenoic acid	100311-78-2	C₃₆H₅₀O₃Si	558.877
——	methyl 12(S)-<(tert-butyldiphenylsilyl)oxy>-5(Z),8(Z),10(E),14(Z)-eicosatetraenoate	100428-43-1	C₃₇H₅₂O₃Si	572.904
——	ethyl-4(S)-<(tert-butyldiphenylsilyl)oxy>-2(E),6(Z)-dodecadienoate	218162-92-6	C₃₀H₄₂O₃Si	478.747
——	methyl-12S-(t-butyldiphenylsilyloxy)eicosa-8Z,10E,14Z-trien-5-ynoate	131485-77-3	C₃₇H₅₀O₃Si	570.888
——	2,2-di(hydroxymethyl)propyl 12S-(t-butyldiphenylsilyloxy)eicosa-5Z,8Z,10E,14Z-tetraenoate	131393-04-9	C₄₁H₆₀O₅Si	661.01
——	(5S,6Z,8E,10E,12R,14Z)-methyl 5,12-bis((tert-butyldiphenylsilyl)oxy)-6,8,10,14-eicosatetraenoate	90108-36-4	C₅₃H₇₀O₄Si₂	827.307
——	2,2-di(hydroxymethyl)propyl-12S-(t-butyldiphenylsilyloxy)eicosa-8Z,10E,14Z-trien-5-ynoate	131393-07-2	C₄₁H₅₈O₅Si	658.994
——	1-(4-methyl-2,6,7-trioxabicyclo<2.2.2>octyl)-11S-(t-butyldiphenylsilyloxy)nonadeca-4Z,7Z,9E,13Z-tetraene	131393-03-8	C₄₁H₅₈O₄Si	642.995
——	1-(4-methyl-2,6,7-trioxabicyclo<2.2.2>octyl)-11S-(t-butyldiphenylsilyloxy)nonadeca-7Z,9E,13Z-trien-4-yne	131393-06-1	C₄₁H₅₆O₄Si	640.979
——	methyl-5,5-(dimethylenedithio)-12(S)-<(tert-butyldiphenylsilyl)oxy>-6(E),10(E),14(Z)-eicosatetraenoate	218162-94-8	C₃₉H₅₄O₃S₂Si	663.073
——	ethyl 5(S)-(benzoyloxy)-12(R)-[(tert-butyldiphenylsilyl)oxy]-6(Z),8(E),10(E),14(Z)-icosatetraenoate	82493-59-2	C₄₅H₅₈O₅Si	707.038

反应信息

作为反应物：

描述：

2(S)-<(tert-butyldiphenylsilyl)oxy>-4(Z)-decenal 在 lithium hydroxide 、四丁基氟化铵、碳酸氢钠、 lithium hexamethyldisilazane 作用下，以四氢呋喃、六甲基磷酰三胺、乙二醇二甲醚、水、甲苯为溶剂，反应 5.0h，生成 12(S-羟基(5Z,8Z,10E,14Z-二十四碳四烯酸

参考文献：

名称：

The total synthesis of 12-HETE (12-hydroxyeicosatetraenoic acid) and 12,20-diHETE

摘要：

DOI：

10.1021/jo00356a004
作为产物：

描述：

hexylidenetriphenylphosphoran 在 lead(IV) acetate 、 sodium carbonate 、三氟乙酸作用下，以四氢呋喃、水为溶剂，反应 16.0h，生成 2(S)-<(tert-butyldiphenylsilyl)oxy>-4(Z)-decenal

参考文献：

名称：

Simple efficient synthesis of LTB4 and 12-epi-LTB4

摘要：

DOI：

10.1016/s0040-4039(00)87415-8

点击查看最新优质反应信息

文献信息

Mosset, P.; Pointeau, P.; Aubert, F., Bulletin de la Societe Chimique de France, 1990, # 2, p. 298 - 315

作者：Mosset, P.、Pointeau, P.、Aubert, F.、Lellouche, J. P.、Beaucourt, J. P.、Gree, R.

DOI：——

日期：——
Cyclopropane-Containing Eicosanoids of Marine Origin. Biomimetic Synthesis of Constanolactones A and B from the Alga Constantinea simplex

作者：James D. White、Mark S. Jensen

DOI：10.1021/ja00128a008

日期：1995.6

Asymmetric syntheses of 7, a substance isolated from incubation of arachidonic acid with an acetone powder of the coral Plexaura homomalla, and of constanolactones A (9) and B (10), metabolites of the red alga Constantinea simplex, are described. The key step involves stannic chloride-mediated cyclization of the oxirane derived from Sharpless epoxidation of 10-hydroxy-5,8-decadienoates, and is shown to yield a trans disubstituted cyclopropane Linked to a delta-lactone. Both (R) and (S) configurations at C5 of the lactone are produced in the cyclization, the ratio being independent of olefin geometry in the acyclic precursor, Elaboration of the cyclization products via Nozaki-Kishi coupling of the derived aldehydes 26 and 37 with the appropriate (1E,5Z)-1-iodo-1,5-undecadiene led to 7, 9, and 10, thereby establishing the relative configuration of 7 and confirming the absolute configuration of 9 and 10.
Synthesis of 5S,12S - diHETE (LTBx)

作者：Julian Adams、Yves Leblanc、Joshua Rokach

DOI：10.1016/s0040-4039(01)80119-2

日期：1984.1
The Total Synthesis of 5-Oxo-12(S)-hydroxy-6(E),8(Z),10(E),14(Z)-eicosatetraenoic Acid and Its 8,9-trans-Isomer and Their Identification in Human Platelets

作者：Subhash P. Khanapure、William S. Powell、Joshua Rokach

DOI：10.1021/jo9813282

日期：1998.11.1

The first total synthesis of 5-oxo-12(S)-hydroxy-6(E),8(Z),10(E), 14(Z)-eicosatetraenoic acid (5-oxo-12-HETE) 6 and its 8-trans-isomer 7 is reported. The synthetic 5-oxo-12-HETE 6 and its 8,9-trans-isomer 7 were used to identify their formation in mixtures of platelets and neutrophils by transcellular metabolism.