(Z)-1-methyl-1-penten-3-ynyl 1-butyl telluride | 142025-07-8

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机含氧阴离子化合物
• 英文名称: (Z)-1-methyl-1-penten-3-ynyl 1-butyl telluride
• 英文别名: (Z)-2-butyltellanylhex-2-en-4-yne
• CAS: 142025-07-8
• 化学式: C₁₀H₁₆Te
• 分子量: 263.837
• InChiKey: DGPNMMPPJRUPIU-NTMALXAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  (Z)-1-methyl-1-penten-3-ynyl 1-butyl telluride 在 正丁基锂 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 2.25h， 生成 tert-butyl-dimethyl-[(3Z)-3-methylhepta-1,3-dien-5-yn-2-yl]oxysilane
  参考文献：
  名称：

  Studies toward (−)-Gymnodimine:  Concise Routes to the Spirocyclic and Tetrahydrofuran Moieties

  摘要：

  (-)-Gymnodimine 是一类具有独特结构的强效海洋毒素的成员，这些毒素在其螺环结构中包含亚胺。本文报告了这一类毒素中四氢呋喃片段的合成、以及针对其螺环亚胺片段的合成策略。关键反应包括：用于确立四氢呋喃立体结构的非对称反式安析尔反应，以及涉及α-甲基烯δ-内酰胺与共轭二烯炔的正式的、分子间的戴斯-阿尔德反应。

  DOI：

  10.1021/ol005510c
• 作为产物：
  描述：

  二丁基二碲 、 2,4-己二炔 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以77%的产率得到(Z)-1-methyl-1-penten-3-ynyl 1-butyl telluride
  参考文献：
  名称：

  Studies toward (−)-Gymnodimine:  Concise Routes to the Spirocyclic and Tetrahydrofuran Moieties

  摘要：

  (-)-Gymnodimine 是一类具有独特结构的强效海洋毒素的成员，这些毒素在其螺环结构中包含亚胺。本文报告了这一类毒素中四氢呋喃片段的合成、以及针对其螺环亚胺片段的合成策略。关键反应包括：用于确立四氢呋喃立体结构的非对称反式安析尔反应，以及涉及α-甲基烯δ-内酰胺与共轭二烯炔的正式的、分子间的戴斯-阿尔德反应。

  DOI：

  10.1021/ol005510c

文献信息

• Synthesis of (E)-1,4-bis(organyl) but-1-en-3-ynes by lithlium-tellurium exchange reaction on (Z)-1-butyltelluro-1,4-bis(organyl) but-1-en-3-ynes.
  作者：Miguel J. Dabdoub、Vânia B. Dabdoub、João V. Comasseto

  DOI：10.1016/s0040-4039(00)74184-0

  日期：1992.4

  react with dibutyl ditelluride and sodium borohydride in ethanol under reflux to give (Z)-1-butyltelluro-1,4-bis(organyl) but-1-en-3-ynes, which by treatment with butyllithium followed by water give (E)-1,4-bis(organyl) but-1-en-3-ynes in high yields.

  1,4-双）有机基）-1,3-丁二炔与二丁基二碲化物和硼氢化钠在乙醇中在回流下反应生成（Z）-1-丁基碲-1,4-双（有机基）but-1-en-3 -ynes，先用丁基锂然后用水处理，以高收率得到（E）-1,4-双（有机基）but-1-en-3-ynes。
• Tellurium in Organic Synthesis. Preparation of <i>Z</i>-Vinylic Cuprates from <i>Z</i>-Vinylic Tellurides and Their Reaction with Enones and Epoxides
  作者：Fábio C. Tucci、André Chieffi、João V. Comasseto、Joseph P. Marino

  DOI：10.1021/jo951547c

  日期：1996.1.1

  Z-Vinylic tellurides, obtained with 100% stereoselectivity by the hydrotelluration of acetylenes, are easily transformed into Z-vinylic higher order cyanocuprates by reaction with preformed Me(2)Cu(CN)Li-2, n-Bu(2)Cu(CN)Li-2, or n-Bu(2-Th)Cu(CN)Li-2, with total retention of the double-bond configuration. The resulting vinylic higher order cyanocuprates react with unhindered enones to give the corresponding 1,4-addition products in good yields. Reaction of the vinylic higher order cyanocuprates with monosubstituted epoxides at 0 degrees C gives the homoallylic alcohols resulting from the attack to the less-substituted carbon atom, while the disubstituted epoxides failed to react. Allylic epoxides react at -78 degrees C with the vinylic higher order cyanocuprates to give mixtures of 1,2- and 1,4-opening products, the 1,4-product predominating. In all cases the double-bond configuration of the original vinylic telluride was preserved. The vinylic cuprates derived from simple vinylic tellurides and conjugated 1-telluroenynes react with epoxides at 0 degrees C, while vinylic cuprates derived from conjugated 1-tellurodienes required the addition of 1 equiv of BF3 . Et(2)O to give the homoallylic alcohols on reaction with epoxides. The opening of optically pure epoxides through tellurium/copper transmetalation is stereospecific, giving one single stereoisomer of the corresponding homoallylic alcohol.
• Iodocyclization of (<i>Z</i>)-1-(Butyltelluro)-1,4-diorganylbut-1-en-3-ynes. Synthesis and Reactions of 3-Iodotellurophenes
  作者：Miguel J. Dabdoub、Vânia B. Dabdoub、Marco A. Pereira、Julio Zukerman-Schpector

  DOI：10.1021/jo961461z

  日期：1996.1.1

  The iodocyclization of(Z)-tellurobutenynes 5a-g by reaction with I-2/petroleum ether was studied in detail. 3-Iodotellurophenes 7a-f were formed, and optimum conditions to obtain these compounds in high yields were established. The reaction involves attack of iodide at the initially formed intermediate of type 10 followed by ring closure that is favored by the strong aromatic character of the resulting products. Two possible and alternative pathways for the ring closure are proposed to explain our observations: (a) transformation of 10 to 11 that undergoes further cyclization to give 7a-f (pathway a) or (b) direct cyclization of 10 to give tellurophene diiodide 9 (pathway b). The products and side products obtained are in agreement with the proposed mechanisms. Formation of 7a from ditelluride 14 and iodine provides additional evidence of the intermediacy of 11 (in pathway a). Structures of 7a and 5g were elucidated by X-ray crystallography. In the case of compound 5e, where a terminal triple bond was present, the resulting intermediate of type 10 also underwent the attack of iodide directly at the terminal carbon to give compound 12 together with 7e. Ring-opening of 3-iodotellurophene 7a occurs by reaction with n-butyllithium to form acyclic ditelluride 14 or monotelluride 16 depending on. the alkyllithium amounts employed. Plausible mechanisms for these novel reactions are proposed and supported. Conversion of 7a to 3-(butyltelluro)-2,5-diphenyltellurophen (22) was carried out readily by an unusual ''aromatic nucleophilic substitution'' using the butyl tellurolate anion.
• Studies toward (−)-Gymnodimine:  Concise Routes to the Spirocyclic and Tetrahydrofuran Moieties
  作者：Ju Yang、Stephen T. Cohn、Daniel Romo

  DOI：10.1021/ol005510c

  日期：2000.3.1

  (-)-Gymnodimine is a member of a unique class of potent marine toxins possessing imines within a spirocylic array. Herein we report the synthesis of the tetrahydrofuran fragment and a strategy toward the spirocyclic imine fragment of this family of toxins. Key reactions include an asymmetric anti-aldol reaction to set the stereochemistry of the tetrahydrofuran and a formal, intermolecular Diels-Alder reaction involving an alpha-methylene-delta-lactam and a dienyne.

  (-)-Gymnodimine 是一类具有独特结构的强效海洋毒素的成员，这些毒素在其螺环结构中包含亚胺。本文报告了这一类毒素中四氢呋喃片段的合成、以及针对其螺环亚胺片段的合成策略。关键反应包括：用于确立四氢呋喃立体结构的非对称反式安析尔反应，以及涉及α-甲基烯δ-内酰胺与共轭二烯炔的正式的、分子间的戴斯-阿尔德反应。