trans-7-bromo-7-trimethylsilyl-cis-norcarane | 43131-20-0

• 分子结构分类: 有机化合物 - 有机盐 - 有机金属盐
• 英文名称: trans-7-bromo-7-trimethylsilyl-cis-norcarane
• CAS: 43131-20-0
• 化学式: C₁₀H₁₉BrSi
• 分子量: 247.25
• InChiKey: JBBKRBNSTZRPOY-ILWJIGKKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.82
• 重原子数：
  12.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  trans-7-bromo-7-trimethylsilyl-cis-norcarane 在 正丁基锂 、 溶剂黄146 作用下， 生成 7-(Trimethylsilyl)bicyclo<4.1.0>heptane
  参考文献：
  名称：

  Synthesis and reactions of 1-bromocyclopropyltrimethylsilane derivatives

  摘要：

  DOI：

  10.1016/s0040-4039(00)87082-3
• 作为产物：
  描述：

  环己烯 、 alkaline earth salt of/the/ methylsulfuric acid 在 potassium tert-butylate 、 magnesium 作用下， 反应 3.0h， 生成 trans-7-bromo-7-trimethylsilyl-cis-norcarane
  参考文献：
  名称：

  Stereoselective ultrasonically induced reductive monosilylation of geminal dibromonorcaranes. Steric effects

  摘要：

  Sonochemical reductive silylation of 1-R-7,7-dibromonorcaranes (R = H, Me, Et, i-Pr) by magnesium produces in each case two 7-bromo-7-trialkylsilylnorcaranes (alkyl = methyl or ethyl). The major isomer is exo (the trialkylsilyl group is cis to the R substituent), but the stereoselectivity of silylation decreases as the alkyl group size at C-l increases, 1-Phenyl-7,7-dibromonorcarane produced a mixture of phenylcycloheptadienes and monobromonorcaranes. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-328x(99)00146-1

文献信息

• Stereospecific routes to the isomeric 7-bromo-7-lithionorcaranes
  作者：Dietmar Seyferth、Robert L. Lambert

  DOI：10.1016/s0022-328x(00)82047-1

  日期：1973.7

  anti-7-Bromo-syn-7-lithionorcarane can be prepared stereospecifically by the reaction of n-butyllithium with 7,7-dibromonorcarane in THF, provided that a slight excess of the dibromo compound is present and the temperature is allowed to rise briefly from −107° to about −93°. syn-7-Bromo-anti-7-lithionorcarane results when n-butyllithium is allowed to react with syn-7-bromo-anti-7-trimethyltinnorearane

  可以通过正丁基锂与7,7-二溴呋喃烷在THF中的反应来立体定向制备抗-7-溴-顺式-7-锂呋喃烷，条件是存在稍微过量的二溴化合物，并允许温度短暂升高从-107°到大约-93°。顺-7-溴反当正丁基锂使之与反应-7- lithionorcarane结果顺-7-溴-反-7- trimethyltinnorearane在THF中在低温下。报道了这些试剂与Me 3 SiCl，Me 3 SnCl，CO 2和C 2 Cl 6的立体定向反应。
• REACTION OF 1-TRIMETHYLSILYLCYCLOPROPYLLITHIUM DERIVATIVES WITH DICHLORO-METHYL METHYL ETHER. A NOVEL SYNTHESIS OF CYCLOPROPYL SILYL KETONES
  作者：Tadashi Nakajima、Masaru Tanabe、Katsuhiko Ohno、Masahito Segi、Sohei Suga

  DOI：10.1246/cl.1986.177

  日期：1986.2.5

  Treatment of 1-trimethylsilylcyclopropyllithium derivatives with dichloromethyl methyl ether affords the corresponding new cyclopropyl silyl ketones in moderate yield. This reaction involves the intramolecular 1,2-silicon shift from carbon to carbon.

  用二氯甲基甲醚处理 1-三甲基甲硅烷基环丙基锂衍生物，以中等产率得到相应的新环丙基甲硅烷基酮。该反应涉及从碳到碳的分子内 1,2-硅转移。
• Stereoselective sonochemical reductive silylation of geminal dibromocyclopropanes by bulk magnesium
  作者：Jonathan Touster、Albert J. Fry

  DOI：10.1016/s0040-4039(97)01453-6

  日期：1997.9

  trimethysilyl chloride and a bicyclic 1,1-dibromocyclopropane in the presence of bulk magnesium affords 1-trimethylsilyl-1-bromocyclopropanes in 72–93% yield. The sonochemical reactions proceed stereoselectively to afford as the major product the product in which the trimethylsilyl group is cis to the hydrogen atoms at the ring juncture.

  在存在大量镁的情况下，用超声波照射同时含有三甲基甲硅烷基氯和双环1，1-二溴环丙烷的THF溶液，可以以72-93％的收率得到1-三甲基甲硅烷基-1-溴环丙烷。声化学反应立体选择性地进行，以提供主要产物，其中三甲基甲硅烷基在环结处与氢原子成顺式。
• Promotion effect of ButOK on the reaction of bromolithiocarbenoids at low temperatures
  作者：Akira Oku、Toshiro Harada、Yukio Homoto、Masaharu Iwamoto

  DOI：10.1039/c39880001490

  日期：——

  carbenoids prepared from 7,7-dibromonorcarane or (2,3-benzocyclohex-2-en-1-ylidene)dichloromethane with butyl-lithium at –85 °C were unreactive at this temperature in tetrahydrofuran (THF) but reacted rapidly with the addition of a stoicheiometric amount of ButOK to give the insertion product with THF, or the addition product with cyclohexane in high yields.

  在–85°C下由7,7-二溴基甲烷或（2,3-苯并环己基-2-烯-1-基）二氯甲烷与丁基锂制备的锂类固醇在此温度下在四氢呋喃（THF）中不反应，但与四氢呋喃迅速反应。此外卜的化学计量量的吨行，得到用THF插入产品，或在高收率环己烷加成产物。
• Acid-catalyzed reaction behavior of 1-silylcyclopropylmethanols
  作者：Mitsunori Honda、Takahito Mita、Toshiaki Nishizawa、Toru Sano、Masahito Segi、Tadashi Nakajima

  DOI：10.1016/j.tetlet.2006.06.002

  日期：2006.8

  Treatment of 1-silylcyclopropylmethanols with TsOH in methanol gives different homoallyl ethers depending upon the configuration of substituents on cyclopropane ring and the kinds of substituents on carbinyl carbon. Especially, the reaction of cyclopropylmethanols having no substituents on the same side with silyl group on cyclopropane ring proceeds to give the corresponding E-homoallyl ethers with

  在甲醇中用 TsOH 处理 1-甲硅烷基环丙基甲醇得到不同的均烯丙基醚，这取决于环丙烷环上取代基的构型和羰基碳上取代基的种类。特别是同侧没有取代基的环丙基甲醇与环丙烷环上的甲硅烷基进行反应，得到相应的具有高立体选择性的E-均烯丙基醚。所得高烯丙基醚的以下原去甲硅烷基化随着构型的保留而进行。