5-(tert-butyldimethylsilyloxy)-1-cyclohexyl-3-iodopent-2-en-1-one | 863912-13-4

• 分子结构分类: 有机化合物
• 英文名称: 5-(tert-butyldimethylsilyloxy)-1-cyclohexyl-3-iodopent-2-en-1-one
• CAS: 863912-13-4
• 化学式: C₁₇H₃₁IO₂Si
• 分子量: 422.422
• InChiKey: DSSVTHYJVJPNQD-FYWRMAATSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.87
• 重原子数：
  21.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  5-(tert-butyldimethylsilyloxy)-1-cyclohexyl-3-iodopent-2-en-1-one 、 2-benzyloxy-5-tributylstannyl-3,4-dihydro-2H-pyran 在 四(三苯基膦)钯 、 copper(l) chloride 、 lithium chloride 作用下， 以 二甲基亚砜 为溶剂， 以81%的产率得到3-(6-benzyloxy-5,6-dihydro-4H-pyran-3-yl)-5-(tert-butyldimethylsilyloxy)-1-cyclohexylpent-2-en-1-ol
  参考文献：
  名称：

  Cu-mediated Stille reactions of sterically congested fragments: towards the total synthesis of zoanthamine

  摘要：

  A study on the Stille reaction of alkenyl iodides and starmanes with structural resemblance to retrosynthetic fragments of a projected total synthesis of the marine alkaloid zoanthamine was carried out. A range of reaction conditions was examined, and a protocol developed by Corey utilizing excess copper(I) chloride and lithium chloride was found to be most efficient. The methodology was successfully applied to join two major fragments of the zoanthamine skeleton. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.06.005
• 作为产物：
  描述：

  5-(tert-butyldimethylsilyloxy)-1-cyclohexyl-3-iodopent-2-en-1-ol 在 四丙基高钌酸铵 、 4 A molecular sieve 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 为溶剂， 以77%的产率得到5-(tert-butyldimethylsilyloxy)-1-cyclohexyl-3-iodopent-2-en-1-one
  参考文献：
  名称：

  Cu-mediated Stille reactions of sterically congested fragments: towards the total synthesis of zoanthamine

  摘要：

  A study on the Stille reaction of alkenyl iodides and starmanes with structural resemblance to retrosynthetic fragments of a projected total synthesis of the marine alkaloid zoanthamine was carried out. A range of reaction conditions was examined, and a protocol developed by Corey utilizing excess copper(I) chloride and lithium chloride was found to be most efficient. The methodology was successfully applied to join two major fragments of the zoanthamine skeleton. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.06.005