(3-(dibromomethylene)dec-1-yn-1-yl)trimethylsilane | 1318244-82-4

• 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: (3-(dibromomethylene)dec-1-yn-1-yl)trimethylsilane
• 英文别名: 3-(Dibromomethylidene)dec-1-ynyl-trimethylsilane
• CAS: 1318244-82-4
• 化学式: C₁₄H₂₄Br₂Si
• 分子量: 380.238
• InChiKey: CWFMVCCGBOADHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.23
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  (3-(dibromomethylene)dec-1-yn-1-yl)trimethylsilane 在 正丁基锂 作用下， 以 正己烷 为溶剂， 反应 1.0h， 以90%的产率得到trimethyl-1,3-undecadiynylsilane
  参考文献：
  名称：

  Chiral Propargyl Alcohols via the Enantioselective Addition of Terminal Di- and Triynes to Aldehydes

  摘要：

  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.

  DOI：

  10.1021/jo2008719
• 作为产物：
  描述：

  1-(trimethylsilyl)dec-1-yn-3-one 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以4.7 g的产率得到(3-(dibromomethylene)dec-1-yn-1-yl)trimethylsilane
  参考文献：
  名称：

  Chiral Propargyl Alcohols via the Enantioselective Addition of Terminal Di- and Triynes to Aldehydes

  摘要：

  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.

  DOI：

  10.1021/jo2008719

文献信息

• 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。
• Cascade and Effective Syntheses of Functionalized Tellurophenes
  作者：Vamsi Krishna Karapala、Hong-Pin Shih、Chien-Chung Han

  DOI：10.1021/acs.orglett.8b00279

  日期：2018.3.16

  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.