4-tert-butyl-1-dibromomethylenecyclohexane | 56881-81-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 4-tert-butyl-1-dibromomethylenecyclohexane
• 英文别名: 1-t-Butyl-4-dibromomethylene-cyclohexane；1-tert-butyl-4-(dibromomethylidene)cyclohexane
• CAS: 56881-81-3
• 化学式: C₁₁H₁₈Br₂
• 分子量: 310.072
• InChiKey: FCQVEXDQGIPKMP-UHFFFAOYSA-N

物化性质

• 沸点：
  287.8±13.0 °C(Predicted)
• 密度：
  1.491±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  4-tert-butyl-1-dibromomethylenecyclohexane 在 palladium diacetate 、 4-甲基苯磺酸吡啶 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 、 乙腈 为溶剂， 生成 2-(4-Tert-butylcyclohexyl)prop-2-enyl-trimethylsilane
  参考文献：
  名称：

  Preparation of 2-trimethylsilylmethyl-1-alkene; cross-coupling and protodesilylation sequence from 1,1-dibromo-1-alkene

  摘要：

  A new method for the preparation of exomethylene type allylsilane is described. Selective mono-protodesilylation of 1-trimethylsityl-2-trimethylsilylmethyl-2-alkenes 2 with PPTS afforded 2-trimethylsilylmethyl-l-alkeiles 4 in excellent yields. Since the resulting allylsilanes 4 possess an exomethylene unit, the reactions of 4 with carbonyl compounds in the presence of Lewis acids gave the corresponding product 7 having an exomethylene unit in excellent yields. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.12.044
• 作为产物：
  描述：

  四溴化碳 、 4-叔丁基环己酮 在 三苯基膦 作用下， 以95%的产率得到4-tert-butyl-1-dibromomethylenecyclohexane
  参考文献：
  名称：

  Preparation of 2-trimethylsilylmethyl-1-alkene; cross-coupling and protodesilylation sequence from 1,1-dibromo-1-alkene

  摘要：

  A new method for the preparation of exomethylene type allylsilane is described. Selective mono-protodesilylation of 1-trimethylsityl-2-trimethylsilylmethyl-2-alkenes 2 with PPTS afforded 2-trimethylsilylmethyl-l-alkeiles 4 in excellent yields. Since the resulting allylsilanes 4 possess an exomethylene unit, the reactions of 4 with carbonyl compounds in the presence of Lewis acids gave the corresponding product 7 having an exomethylene unit in excellent yields. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.12.044

文献信息

• Trifluoromethylation of aliphatic halides with trifluoromethyl copper
  作者：Yoshiro Kobayashi、Kenjiro Yamamoto、Itsumaro Kumadaki

  DOI：10.1016/s0040-4039(01)86506-0

  日期：1979.1

  A solution of trifluoromethyl copper complex in hexamethylphosphoric triamide was found to be useful for trifluoromethylation of aliphatic halides.

  发现三氟甲基铜络合物在六甲基磷酸三酰胺中的溶液可用于脂族卤化物的三氟甲基化。
• Generation and alkylation reaction of 1-bromoalkenylzincate
  作者：Toshiro Harada、Daiji Hara、Kazuhiro Hattori、Akira Oku

  DOI：10.1016/s0040-4039(00)82124-3

  日期：1988.1
• Reactions of 1,1-dihaloalkenes with triorganozincates: a novel method for the preparation of alkenylzinc species associated with carbon-carbon bond formation
  作者：Toshiro Harada、Takeshi Katsuhira、Daiji Hara、Yasuo Kotani、Keiji Maejima、Ryousuke Kaji、Akira Oku

  DOI：10.1021/jo00070a027

  日期：1993.8

  Lithium trialkylzincates react with 1,1-dibromoalkenes 1 and 1-bromo-1-chloroalkenes 2 at -85-degrees-C in THF to give 1-bromoalkenes 5 and 1-chloroalkenes 7, respectively, upon hydrolysis. The intermediate (1-haloalkenyl)zincates 4 and 6 are stable at low temperature but, when allowed to warm to 0-degrees-C, they undergo a 1,2-alkyl migration reaction to afford alkenylzinc species 10. A variety of alkylation products 11 are obtained by the hydrolysis of 10. In the presence of (Ph3P)2Pd (5 mol%), alkenylzinc species 10 react smoothly with organic halides (AcCl, EtOCOCl, CH2=CH-(Me)Br, PhBr) to yield the corresponding coupling products 13-16.
• Preparation of 1,1-Dibromoalkenes by Halogen Exchange
  作者：Philippe SAVIGNAC、Philippe COUTROT

  DOI：10.1055/s-1976-23989

  日期：——
• Molecular-Recognition-Directed Self-Assembly of Pleated Sheets from 2-Aminopyrimidine Hydrogen-Bonding Motifs
  作者：Michael J. Krische、Jean-Marie Lehn、Nathalie Kyritsakas、Jean Fischer

  DOI：10.1002/(sici)1522-2675(19981111)81:11<1909::aid-hlca1909>3.0.co;2-0

  日期：1998.11.11

  The self-assembly of the 2,2'-diamino-5,5'-(dialkylmethylidene)methylenedipyrimidine derivatives 3a-c allows for the molecular-recognition-directed generation of pleated sheets as revealed by X-rap crystallographic analysis. The data provide insight into the interplay of the different structural and interactional features of the molecular components in the generation of the supramolecular assembly. The introduction of the adamantylidene group as in 3c leads to the dominance of the H-bonding factor and the resulting formation of a regular, fully interconnected array of pleated sheet type. The results suggest further manipulation of the interplay of the different factors to induce the self-assembly of other supramolecular architectures.