1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-iodo-3-triethylsilanyloxy-cyclopentene | 186960-07-6

• 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: 1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-iodo-3-triethylsilanyloxy-cyclopentene
• CAS: 186960-07-6
• 化学式: C₁₈H₃₇IO₂Si₂
• 分子量: 468.566
• InChiKey: GCEXVKROCNZXJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.88
• 重原子数：
  23.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  tert-butyl-[(2Z)-2-iodopenta-2,4-dienoxy]-dimethylsilane 、 1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-iodo-3-triethylsilanyloxy-cyclopentene 在 四(三苯基膦)钯 正丁基锂 、 zinc dibromide 作用下， 生成 1-(tert-Butyl-dimethyl-silanyloxymethyl)-3-triethylsilanyloxy-cyclopentene 、 1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-[(E)-1-(tert-butyl-dimethyl-silanyloxymethyl)-buta-1,3-dienyl]-3-triethylsilanyloxy-cyclopentene
  参考文献：
  名称：

  An efficient and selective synthesis of nakienone A involving a novel protocol for α-alkenylation of ketones via palladium-catalyzed alkenyl-alkenyl coupling

  摘要：

  Nakienone A was synthesized for the first time from 3-methoxy-2-cyclopentenone, dienyl iodide 7, and LICH(2)OMOM in 8 steps in 26% overall yield with full control of the alkene geometry using the Pd-catalyzed cross coupling reaction of a cyclopentenylzinc derivative 6a with 7 as a key step. (C) 1997, Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(96)02409-4
• 作为产物：
  描述：

  3-Hydroxymethyl-2-iodo-cyclopent-2-enone 在 咪唑 、 sodium tetrahydroborate 、 cerium(III) chloride 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.08h， 生成 1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-iodo-3-triethylsilanyloxy-cyclopentene
  参考文献：
  名称：

  An efficient and selective synthesis of nakienone A involving a novel protocol for α-alkenylation of ketones via palladium-catalyzed alkenyl-alkenyl coupling

  摘要：

  Nakienone A was synthesized for the first time from 3-methoxy-2-cyclopentenone, dienyl iodide 7, and LICH(2)OMOM in 8 steps in 26% overall yield with full control of the alkene geometry using the Pd-catalyzed cross coupling reaction of a cyclopentenylzinc derivative 6a with 7 as a key step. (C) 1997, Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(96)02409-4