(4,4-二溴-3-苯基丁-3-烯-1-炔-1-基)三甲基硅烷 | 879560-00-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (4,4-二溴-3-苯基丁-3-烯-1-炔-1-基)三甲基硅烷
• 英文名称: (4,4-dibromo-3-phenylbut-3-en-1-yn-1-yl)trimethylsilane
• 英文别名: (4,4-Dibromo-3-phenylbut-3-en-1-ynyl)-trimethylsilane
• CAS: 879560-00-6
• 化学式: C₁₃H₁₄Br₂Si
• 分子量: 358.148
• InChiKey: AFPUGLLBTMPZIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.03
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 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：

  (4,4-二溴-3-苯基丁-3-烯-1-炔-1-基)三甲基硅烷 在 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 以93%的产率得到(1,1-二溴丁-1-烯-3-炔-2-基)苯
  参考文献：
  名称：

  一锅合成和功能化的聚炔。

  摘要：

  [反应：见正文]据报道，一锅法合成和衍生了二炔和三炔。聚炔骨架是由基于类胡萝卜素重排的二溴代烯烃前体形成的，然后用亲电子试剂将所得的乙炔基锂原位捕获，以提供官能化的二炔和三炔。备选地，Li-乙炔化物中间体的重金属化提供了Zn-或Sn-乙炔化物，其然后允许经由钯催化的交叉偶联反应而发散地制备二芳基聚炔或芳基炔酮。

  DOI：

  10.1021/ol0528888
• 作为产物：
  描述：

  苯甲醛 在 重铬酸吡啶 、 正丁基锂 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 (4,4-二溴-3-苯基丁-3-烯-1-炔-1-基)三甲基硅烷
  参考文献：
  名称：

  Cascade and Effective Syntheses of Functionalized Tellurophenes

  摘要：

  A one-pot and transition-metal-catalyst-free synthetic strategy to construct functionalized tellurophenes has been developed. Substituted 1,1-dibromo-l-en-3-ynes are smoothly converted to tellurophenes with telluride salts in high yield via a series of cascade reactions through reductive debromination, hydrotelluration, nucleophilic cyclization, and aromatization. Close inspection of the results clearly showed that the reactivity of in situ prepared telluride salts are significantly influenced by the polarity of the solvent system and the electronic nature of the substituent on the enyne substrate. This method reports the first direct synthesis of 3-aryltellurophenes in high yields at room temperature. This novel reaction strategy is also found to be a promising synthetic method for multisubstituted tellurophenes and selenophenes.

  DOI：

  10.1021/acs.orglett.8b00279

文献信息

• One-Pot Synthesis and Functionalization of Polyynes via Alkylidene Carbenoids
  作者：Rik Tykwinski、Thanh Luu、Yasuhiro Morisaki

  DOI：10.1055/s-2007-1000937

  日期：——

  one-pot, two-step method for the synthesis of diynes and triynes is reported. The reaction of a dibromoolefinic precursor with BuLi effects a Fritsch-Buttenberg-Wiechell rearrangement and generates a lithium acetylide intermediate, which is then trapped with a variety of electrophiles to produce substituted diynes and triynes. Alternatively, transmetalation from the lithium acetylide to give a zinc acetylide

  报道了一种合成二炔和三炔的一锅两步法。二溴烯烃前体与 BuLi 的反应会产生 Fritsch-Buttenberg-Wiechell 重排并生成乙炔锂中间体，然后用各种亲电子试剂捕获该中间体以产生取代的二炔和三炔。或者，从乙炔锂的金属转移得到乙炔锌为芳基碘化物在钯存在下通过根岸偶联形成对称或不对称的二炔和三炔提供了亲核偶联配偶体。
• Method for synthesis of chalcogenophenes
  申请人：National Tsing Hua University

  公开号：US10407402B1

  公开（公告）日：2019-09-10

  A method of forming a chalcogenophene compound of formula (I) includes reacting a compound of formula (II) with a chalcogenide salt in presence of a proton source. Y is O, S, Se, Te or Po. R1 is hydrogen, deuterium, an aliphatic, heteroaromatic, or aromatic group, or a precursor of a leaving group Z whose conjugate acid (HZ) has pKa less than 30. R2 is hydrogen, deuterium, or an aliphatic, heteroaromatic, or aromatic group. R1 and R2 may be the same or different, and may joint together to form a saturated or unsaturated, heteroalicyclic or alicyclic ring. R3 is, for example, alkyl, aryl, heteroaryl, organosilyl, organotin, or organogermyl. R3′ is the same as R3 or is hydrogen. X is a precursor of a leaving group X whose conjugate acid (HX) has a pKa of less than 30.

  将式(I)的硫锗烯化合物的形成方法包括在质子源存在下，将式(II)的化合物与硫化物盐反应。Y为O、S、Se、Te或Po。R1为氢、氘、脂肪族、杂环芳烃或芳香族基团，或具有pKa小于30的离去基团Z的前体的共轭酸(HZ)。R2为氢、氘或脂肪族、杂环芳烃或芳香族基团。R1和R2可以相同也可以不同，并且可以联合形成饱和或不饱和的、杂环或脂环的环。R3例如是烷基、芳基、杂芳基、有机硅基、有机锡基或有机锗基。R3'与R3相同或为氢。X是具有pKa小于30的共轭酸(HX)的离去基团X的前体。
• Chiral Propargyl Alcohols via the Enantioselective Addition of Terminal Di- and Triynes to Aldehydes
  作者：Erin R. Graham、Rik R. Tykwinski

  DOI：10.1021/jo2008719

  日期：2011.8.19

  The enantioselective addition of di- and triynes to aldehydes is presented, including the first examples of an asymmetric triyne addition. Modification of the Carreira alkynylation protocol shows that addition of diynes and triynes to alpha-branched aldehydes can be complete in as little as 4 h, and these reactions give good yields and enantioselectivities (up to 98% ee) for di- and triynes tested (aryl, alkyl, and silyl). It is shown for two cases (20 and 24) that products of this asymmetric addition reaction can undergo further manipulation (desilylation and triazole formation) without affecting the enantiopurity.
• Synthesis and 13C NMR Spectroscopy of 13C-Labeled α,ω-Diphenylpolyynes
  作者：Rik Tykwinski、Thanh Luu

  DOI：10.1055/s-0031-1290983

  日期：2012.6

  The synthesis of three C-13-labeled alpha,omega-diphenylpolyynes is described. The known positions of the labeled carbon atoms allow assignment of the resonances in the C-13 NMR spectra and identification of trends in the chemical shifts.