3-(tert-Butyl-dimethyl-silanyloxymethyl)-2-[(E)-1-(tert-butyl-dimethyl-silanyloxymethyl)-buta-1,3-dienyl]-cyclopent-2-enone | 186960-05-4

• 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-(tert-Butyl-dimethyl-silanyloxymethyl)-2-[(E)-1-(tert-butyl-dimethyl-silanyloxymethyl)-buta-1,3-dienyl]-cyclopent-2-enone
• 英文别名: 3-[[tert-butyl(dimethyl)silyl]oxymethyl]-2-[(2E)-1-[tert-butyl(dimethyl)silyl]oxypenta-2,4-dien-2-yl]cyclopent-2-en-1-one
• CAS: 186960-05-4
• 化学式: C₂₃H₄₂O₃Si₂
• 分子量: 422.756
• InChiKey: JOXZVRHMJVTMBL-AQTBWJFISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(tert-Butyl-dimethyl-silanyloxymethyl)-2-[(E)-1-(tert-butyl-dimethyl-silanyloxymethyl)-buta-1,3-dienyl]-cyclopent-2-enone 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以84%的产率得到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 、 sodium acetate 、 potassium carbonate 、 三乙胺 、 pyridinium chlorochromate 、 zinc dibromide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 26.08h， 生成 3-(tert-Butyl-dimethyl-silanyloxymethyl)-2-[(E)-1-(tert-butyl-dimethyl-silanyloxymethyl)-buta-1,3-dienyl]-cyclopent-2-enone
  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.