(E)-1-lithio-3-<(tert-butyldimethylsilyl)oxy>-1-octene | 39178-67-1

• 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
• 英文名称: (E)-1-lithio-3-<(tert-butyldimethylsilyl)oxy>-1-octene
• 英文别名: (1E)-1-lithio-3-<(tert-butyldimethylsilyl)oxy>-1-octene
• CAS: 39178-67-1
• 化学式: C₁₄H₂₉LiOSi
• 分子量: 248.41
• InChiKey: MBAZVNLUSWEGPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.57
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-1-lithio-3-<(tert-butyldimethylsilyl)oxy>-1-octene 在 vanadyl acetylacetonate chromium(VI) oxide 、 叔丁基过氧化氢 、 potassium fluoride 、 pH 7 phosphate buffer 、 氢氟酸 、 lithium diisopropyl amide 作用下， 以 乙醇 、 二氯甲烷 、 水 、 乙腈 、 苯 为溶剂， 反应 47.0h， 生成 1,11ALPHA,15S-TRIHYDROXY-PROST-13E-EN-9-ONE
  参考文献：
  名称：

  Regio- and stereoselectivity of the reaction between cyanocuprates and cyclopentene epoxides. Application to the total synthesis of prostaglandins

  摘要：

  DOI：

  10.1021/jo00231a014
• 作为产物：
  描述：

  3-[(tert-butyldimethylsilyl)oxy]-1-(tributhylstannyl)-1(E)-octene 生成 (E)-1-lithio-3-<(tert-butyldimethylsilyl)oxy>-1-octene
  参考文献：
  名称：

  IKEHGAMI, SIRO;XASIMOTO, SINITI;KUROSUMI, SEHJDZI

  摘要：

  DOI：

文献信息

• Stereospecific synthesis of dienes and trienes from pyrylium perchlorate: a convergent approach to leukotrienes
  作者：Mark Furber、Richard J. K. Taylor

  DOI：10.1039/c39850000782

  日期：——

  A range of conjugated dienes and trienes have been prepared in a stereospecific manner by the treatment of pyrylium perchlorate with organolithium reagents; model studies have been carried out which demonstrate the suitability of this methodology for the synthesis of leukotriene B4.

  通过用有机锂试剂处理高氯酸吡啶鎓，以立体有择的方式制备了一系列共轭二烯和三烯。已经进行了模型研究，证明了该方法适用于白三烯B 4的合成。
• 2-Acyl-3-substituted cyclopentan-1-ones and process for their preparation
  申请人：Teijin Limited

  公开号：US04009196A1

  公开（公告）日：1977-02-22

  1,3-Dicarbonyl compounds useful as medicines, agricultural chemicals, perfumes, and their intermediates are prepared by reacting a specific .alpha.,.beta.-unsaturated carbonyl compound with a specific organic copper lithium compound in the presence of an aprotic inert organic solvent, and then reacting the reaction product with an organic carboxylic acid halide or anhydride. In particular, novel 2-acyl-3-substituted cyclopentan-1-ones and 2-acyl-3-substituted cyclohexan-1-ones having important physiological activities are provided.

  具有药物、农药、香料和中间体用途的1,3-二羰基化合物可通过在无水惰性有机溶剂中反应特定的α,β-不饱和羰基化合物与特定的有机铜锂化合物，然后将反应产物与有机羧酸卤化物或酐反应制备而成。特别地，提供了具有重要生理活性的新型2-酰基-3-取代环戊-1-酮和2-酰基-3-取代环己-1-酮。
• Process for preparation of adjacently disubstituted ketones
  申请人：Teitin Limited

  公开号：US04315032A1

  公开（公告）日：1982-02-09

  A novel 7-hydroxyprostaglandin E.sub.1, or a stereoisomer thereof, or a protected derivative thereof, having the following formula: ##STR1## wherein R.sup.8 represents H, CH.sub.3 or C.sub.2 H.sub.5, R.sup.9 represents H or CH.sub.3, R.sup.10 and R.sup.11 are identical or different, and each represents H, tetrahydropyranyl or t-butyldimethylsilyl. Also provided is a process for producing an adjacently disubstituted ketone including the above compounds, i.e. 7-oxoprostaglandin, etc. which comprises reacting an .alpha.,.beta.-unsaturated carbonyl compound with a cuprous salt and an organolithium compound in an aprotic inert organic medium in the presence of trialkylphosphine, the amounts of said cuprous salt and said organolithium compound being substantially equimolar, and reacting the product with a protected acetal derivative of an organic carbonyl compound or an aldehyde in the presence of a Lewis acid, if necessary, followed by reacting the product with a proton donor.

  一种新型的7-羟基前列腺素E.sub.1，或其立体异构体，或其保护衍生物，其化学式如下：##STR1## 其中R.sup.8代表H，CH.sub.3或C.sub.2H.sub.5，R.sup.9代表H或CH.sub.3，R.sup.10和R.sup.11相同或不同，且每个代表H，四氢吡喃基或叔丁基二甲基硅基。还提供了一种生产上述化合物，即7-氧代前列腺素等相邻二取代酮的方法，包括在无水惰性有机介质中，在三烷基膦的存在下，将α，β-不饱和羰基化合物与铜盐和有机锂化合物反应，所述铜盐和有机锂化合物的量基本相等，并在需要时在路易斯酸的存在下将产物与有机羰基化合物或醛的保护缩醛衍生物反应，然后将产物与质子供体反应。
• 1,3-Dicarbonyl compounds
  申请人：Teijin Limited

  公开号：US04139717A1

  公开（公告）日：1979-02-13

  1,3-Dicarbonyl compounds useful as medicines, agricultural chemicals, perfumes, and their intermediates are prepared by reacting a specific .alpha.,.beta.-unsaturated carbonyl compound with a specific organic copper lithium compound in the presence of an aprotic inert organic solvent, and then reacting the reaction product with an organic carboxylic acid halide or anhydride. In particular, novel 2-acyl-3-substituted cyclopentan-1-ones and 2-acyl-3-substituted cyclohexan-1-ones having important physiological activities are provided.

  本发明提供了一种制备用于药物、农药、香料以及它们的中间体的1,3-二羰基化合物的方法，其通过在无极性惰性有机溶剂存在下，将特定的α，β-不饱和羰基化合物与特定的有机铜锂化合物反应，然后将反应产物与有机羧酸卤化物或酐反应而得。特别地，本发明提供了具有重要生理活性的新型2-酰基-3-取代环戊酮和2-酰基-3-取代环己酮。
• Novel Three-Component Coupling Using Aluminum Tris(2,6-diphenylphenoxide) (ATPH): The Same Synthetic Strategy Leads to trans- and cis-Jasmonates
  作者：Susumu Saito、Satoko Yamazaki、Hisashi Yamamoto

  DOI：10.1002/1521-3773(20011001)40:19<3613::aid-anie3613>3.0.co;2-3

  日期：2001.10.1