[(4R)-4-[tert-butyl(dimethyl)silyl]oxycyclohexa-1,5-dien-1-yl] acetate | 1199940-92-5

• 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: [(4R)-4-[tert-butyl(dimethyl)silyl]oxycyclohexa-1,5-dien-1-yl] acetate
• CAS: 1199940-92-5
• 化学式: C₁₄H₂₄O₃Si
• 分子量: 268.428
• InChiKey: DYRJRQUYSNUDLP-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.78
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  [(4R)-4-[tert-butyl(dimethyl)silyl]oxycyclohexa-1,5-dien-1-yl] acetate 在 2,6-二甲基吡啶 、 六甲基磷酰三胺 、 samarium diiodide 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 27.33h， 生成 (1S,2S,3R,6S,8R,10S,11R)-11-[tert-butyl(dimethyl)silyl]oxy-3-methyl-5-phenyl-8-triethylsilyloxy-7-oxa-5-azatetracyclo[6.4.0.02,6.03,10]dodecan-4-one
  参考文献：
  名称：

  Controlling the Facial Selectivity of Asymmetric [4 + 2] Cyclo-additions: A Concise Synthesis of the cis-Decalin Core Structure of Superstolides A and B

  摘要：

  Reglo-, stereo-, and facial selective [4 + 2] cycloadditions between highly activated vinyl sulfones and 1,3-dienes derived from (R)-4-tert-wbutyldimethylsilyloxy-2-cyclohexen-1-one provide a powerful approach for the asymmetric synthesis of compounds containing the bicyclo[2.2.2]octanone carbon skeleton. This new methodology has been successfully applied to the asymmetric synthesis of the cis-decalin core structure of the potent anticancer marine natural products superstolides A and B.

  DOI：

  10.1021/ol201095b
• 作为产物：
  描述：

  乙酸酐 、 (4R)-4-((tert-butyldimethylsilyl)oxy)cyclohex-2-en-1-one 在 lithium diisopropyl amide 作用下， 以90%的产率得到[(4R)-4-[tert-butyl(dimethyl)silyl]oxycyclohexa-1,5-dien-1-yl] acetate
  参考文献：
  名称：

  Asymmetric [4+2] cycloadditions employing 1,3-dienes derived from (R)-4-t-butyldimethyl-silyloxy-2-cyclohexen-1-one

  摘要：

  1,3-Dienes derived from (R)-4-t-butyldimethylsilyloxy-2-cyclohexen-1-one react with activated dienophiles to form predominately (or sometimes exclusively) syn/endo products. These controlled [4+2] cycloadditions increase the asymmetric complexity from one asymmetric center in the starting material to five asymmetric centers in the products in a single step, and provide a powerful approach for the asymmetric synthesis of compounds containing the bicyclo[2.2.2]octanone carbon skeleton. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.09.055

文献信息

• Diastereoselective acyl nitroso Diels-Alder reactions using 1,3-dienes derived from (R)-4-tert-butyldimethylsilyloxy-2-cyclohexen-1-one
  作者：Dengfu Lu、Lei Chen、Avishek Roy、Zhendong Jin

  DOI：10.1016/j.tetlet.2023.154367

  日期：2023.3

  xen-1-one react with acyl nitroso dienophiles to form exclusively anti [4 + 2] cycloaddition products. These regio and diastereoselective acyl nitroso Diels-Alder reactions increase the asymmetric complexity from one chiral center in the starting material to three chiral centers in the products in a single step and provide a powerful approach for the asymmetric synthesis of compounds containing 3,6-dihydro-1

  衍生自 ( R )-4- t -butyldimethylsilyloxy-2-cyclohexen-1-one 的 1,3-Diene 与酰基亚硝基亲二烯体反应生成完全抗[4 + 2] 环加成产物。这些区域选择性和非对映选择性酰基亚硝基 Diels-Alder 反应在一步中将不对称复杂性从起始材料中的一个手性中心增加到产物中的三个手性中心，并为含 3,6-二氢化合物的不对称合成提供了一种强有力的方法-1,2-恶嗪结构特征。