(6-hydroxyhex-2-enyl)trimethylsilane | 119554-57-3

• 分子结构分类: 有机化合物 - 有机盐 - 有机金属盐
• 英文名称: (6-hydroxyhex-2-enyl)trimethylsilane
• 英文别名: 6-(trimethylsilyl)-4-hexen-1-ol；6-trimethylsilyl-hex-4-en-1-ol；6-Trimethylsilyl-4-hexen-1-ol；6-(Trimethylsilyl)hex-4-en-1-ol；6-trimethylsilylhex-4-en-1-ol
• CAS: 119554-57-3
• 化学式: C₉H₂₀OSi
• 分子量: 172.343
• InChiKey: DSCUBQMRFPPONQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.65
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (6-hydroxyhex-2-enyl)trimethylsilane 在 咪唑 、 碘 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以96%的产率得到(6-iodo-2-hexenyl)trimethylsilane
  参考文献：
  名称：

  高非对映选择性合成取代吡咯烷的使用亚甲亚胺叶立德环加成和亲核环化的序列。

  摘要：

  尽管偶氮甲亚烷基的环加成反应通常会提供内/外加合物的混合物，但我们成功地调节了新反应级联的机理，从而以高收率和非对映体纯度提供了取代的吡咯烷。这是通过迫使锡或硅取代的亚胺离子脱金属，然后进行甲亚胺叶立德环加成和亲核环化来实现的。因此，在完全受控的一锅反应级联反应中，迅速建立了结构复杂性。

  DOI：

  10.1021/ol902767b
• 作为产物：
  描述：

  6-t-butyldimethylsiloxy-1-trimethylsilyl-2-hexene 在 4-甲基苯磺酸吡啶 作用下， 以 乙醇 为溶剂， 反应 20.0h， 以71%的产率得到(6-hydroxyhex-2-enyl)trimethylsilane
  参考文献：
  名称：

  Generation of the Dihydro-5H-Thiazolo[3,2-a]pyridin-3-one Ring System by Proton Loss from Isothiomünchnones

  摘要：

  Dihydro-5H-thiazolo[3,2-a]pyridin-3-ones are easily generated by proton loss from isothiomunchnones. The closely related tetrahydro-2H-pyrido[2,1-b]-[1,3]thiazin-4-one ring system was prepared by treating piperidine-2-thione with acryloyl chloride. These cyclic S,N-ketene acetals undergo smooth reaction with different electrophiles in the presence of Lewis acids.

  DOI：

  10.3987/com-93-s32

文献信息

• New Method for Derivatization of Squaric Acid to Highly Substituted Cyclobutenones: Lewis Acid-Catalyzed Reaction of Cyclobutene-1,2-dione Monoacetal and Its Vinylog with Unsaturated Organosilanes, and Subsequent Ring Transformation of the Adducts
  作者：Yoshihiko Yamamoto、Masatomi Ohno、Shoji Eguchi

  DOI：10.1246/bcsj.69.1353

  日期：1996.5

  Described herein is a novel method for regio-controlled synthesis of highly substituted cyclobutenones having an unsaturated substituent at 4-position, starting from commercially available squaric acid. Both cyclobutene-1,2-dione monoacetal (4,4-diethoxycyclobutenone) and its vinylog (2,4-diethoxycyclobutenone), which were easily obtained from diethyl squarate, reacted with allylsilanes in the presence

  本文描述了一种区域控制合成在 4 位具有不饱和取代基的高度取代的环丁烯酮的新方法，起始于可商购的方酸。环丁烯-1,2-二酮单缩醛（4,4-二乙氧基环丁烯酮）及其乙烯基（2,4-二乙氧基环丁烯酮）很容易从方酸二乙酯中获得，在 Et2O·BF3 存在下与烯丙基硅烷反应得到 4-烯丙基-4-乙氧基环丁烯酮在 2 位区域选择性地具有各种取代基。这些产物通过在二甲苯中回流有效地转化为高度取代的双环[3.2.0]庚烯酮。该方法的合成效用在三环系统的构建中得到了证明。使用丙二烯基硅烷、甲硅烷基烯醇醚进一步扩展路易斯酸催化的单缩醛反应，和甲硅烷基乙烯酮缩醛也提供相应的 4-取代产物。与上述 4-烯丙基化产物相比，4-炔丙基化和 4-酰基甲基化的 p...
• Moret, Eticnne; Franzini, Livia; Schlosser, Manfred, Chemische Berichte, 1997, vol. 130, # 3, p. 335 - 339
  作者：Moret, Eticnne、Franzini, Livia、Schlosser, Manfred

  DOI：——

  日期：——
• About the Stereoelectronics of the Intramolecular Addition of Allylsilanes to Aldehydes
  作者：Manfred Schlosser、Livia Franzini、Carsten Bauer、Frédéric Leroux

  DOI：10.1002/1521-3765(20010504)7:9<1909::aid-chem1909>3.3.co;2-8

  日期：2001.5.4

  (Z)-omega -Trimethylsilyl-(omega -2)-alken-1-ols are readily accessible by consecutive superbase metalation and silylation of (omega -1)-alken-1-ols. These versatile intermediates may be oxidized to give the corresponding (Z)-omega -trimethylsilyl-(omega -2)-alkenals which, in the presence of trifluoroacetic acid, can be converted into 2-vinylcycloalkanols such as 2-vinylcyclohexanol (2), isopulegol (4), and bis(2 vinylcyclobutyl) ether (8). The stereochemical outcome of these cyclization reactions suggests the interference of a novel electrodynamic effect.
• Intramolecular Cyclization of Tethered Phenyl Ketones. Complementary Stereochemical Results Arising from the Indium-Promoted Ring Closure of Allyl Bromides and the Fluoride Ion-Induced Desilylation of Allylsilanes
  作者：Leo A. Paquette、José L. Mendez-Andino

  DOI：10.1021/jo981683s

  日期：1998.11.1

  dThe intramolecular indium-promoted cyclization of 4'-substituted (Z)- and (E)-7-bromo-5-heptenophenones has been examined in aqueous tetrahydrofuran. In every instance, ring closure occurred to deliver the syn-2-vinylcyclopentanol exclusively. The corresponding allylsilanes have been prepared as well, and the course of their fluoride ion-induced cyclization was also studied. In these systems, a kinetic bias for formation of the anti-2-vinylcyclopentanol is observed, although not with the same exclusivity. Accordingly, complementarity in product diastereoselectivity can be realized in purposeful fashion. The data acquired in this investigation suggest that the indium-catalyzed reactions involve intramolecularly coordinated transition states where development of a cis 5/6-bicyclic framework is most energetically feasible. In contrast, the silanes appear to utilize open-chain antiperiplanar transition states. While the latter are not particularly sensitive to double-bond geometry, they are responsive to steric compression involving the aryl group.
• Generation of the Dihydro-5H-Thiazolo[3,2-a]pyridin-3-one Ring System by Proton Loss from Isothiomünchnones
  作者：Albert Padwa、Zhijia J. Zhang

  DOI：10.3987/com-93-s32

  日期：——

  Dihydro-5H-thiazolo[3,2-a]pyridin-3-ones are easily generated by proton loss from isothiomunchnones. The closely related tetrahydro-2H-pyrido[2,1-b]-[1,3]thiazin-4-one ring system was prepared by treating piperidine-2-thione with acryloyl chloride. These cyclic S,N-ketene acetals undergo smooth reaction with different electrophiles in the presence of Lewis acids.