1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-[(E)-1-(tert-butyl-dimethyl-silanyloxymethyl)-buta-1,3-dienyl]-3-trimethylsilanyloxy-cyclopentene | 186960-02-1

• 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-[(E)-1-(tert-butyl-dimethyl-silanyloxymethyl)-buta-1,3-dienyl]-3-trimethylsilanyloxy-cyclopentene
• 英文别名: tert-butyl-[(2E)-2-[2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-trimethylsilyloxycyclopenten-1-yl]penta-2,4-dienoxy]-dimethylsilane
• CAS: 186960-02-1
• 化学式: C₂₆H₅₂O₃Si₃
• 分子量: 496.954
• InChiKey: MHEGFSJLEBYCMM-PGMHBOJBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.45
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-[(E)-1-(tert-butyl-dimethyl-silanyloxymethyl)-buta-1,3-dienyl]-3-trimethylsilanyloxy-cyclopentene 在 四丁基氟化铵 、 sodium acetate 、 potassium carbonate 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 为溶剂， 反应 3.17h， 生成 nakienone A
  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-(tert-Butyl-dimethyl-silanyloxymethyl)-2-iodo-cyclopent-2-enone 在 Cl2Pd2 sodium tetrahydroborate 、 正丁基锂 、 cerium(III) chloride 、 三乙胺 、 zinc dibromide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 23.08h， 生成 1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-[(E)-1-(tert-butyl-dimethyl-silanyloxymethyl)-buta-1,3-dienyl]-3-trimethylsilanyloxy-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

文献信息

• An efficient and selective synthesis of nakienone A involving a novel protocol for α-alkenylation of ketones via palladium-catalyzed alkenyl-alkenyl coupling
  作者：Milan Pour、Ei-ichi Negishi

  DOI：10.1016/s0040-4039(96)02409-4

  日期：1997.1

  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.