2-[(1S,3S)-3-(tert-butyldimethylsilyloxy)-2,2-dimethyl-6-methylidenecyclohexyl]iodoethane | 615562-18-0

• 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: 2-[(1S,3S)-3-(tert-butyldimethylsilyloxy)-2,2-dimethyl-6-methylidenecyclohexyl]iodoethane
• 英文别名: tert-butyl-[(1S,3S)-3-(2-iodoethyl)-2,2-dimethyl-4-methylidenecyclohexyl]oxy-dimethylsilane
• CAS: 615562-18-0
• 化学式: C₁₇H₃₃IOSi
• 分子量: 408.438
• InChiKey: LNARTNUUWLEWMX-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.19
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-[(1S,3S)-3-(tert-butyldimethylsilyloxy)-2,2-dimethyl-6-methylidenecyclohexyl]iodoethane 在 N-碘代丁二酰亚胺 、 四丁基氟化铵 、 叔丁基锂 、 8-甲氧基-9-硼杂双环[3.3.1]壬烷 作用下， 以 四氢呋喃 、 various solvents 、 乙腈 为溶剂， 反应 23.42h， 生成 (1R,2R,4S)-2-[2-(5,8-dimethoxynaphthalen-2-yl)ethyl]-1-(iodomethyl)-3,3-dimethyl-7-oxabicyclo[2.2.1]heptane
  参考文献：
  名称：

  Synthesis of cordiaquinone J and K via B-alkyl Suzuki–Miyaura coupling as a key step and determination of the absolute configuration of natural products

  摘要：

  A versatile methodology for the synthesis of various terpenoids via B-alkyl Suzuki-Miyaura coupling as a key step is established. Synthesis of cordiaquinone J and K, new antifungal and larvicidal meroterpenoids, was achieved by using this methodology. The absolute configurations of cordiaquinone J and K were confirmed by the synthesis. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.06.115
• 作为产物：
  描述：

  Toluene-4-sulfonic acid 2-[(1S,3S)-3-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-6-methylene-cyclohexyl]-ethyl ester 在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 4.0h， 以5.91 g的产率得到2-[(1S,3S)-3-(tert-butyldimethylsilyloxy)-2,2-dimethyl-6-methylidenecyclohexyl]iodoethane
  参考文献：
  名称：

  Synthesis of cordiaquinone J and K via B-alkyl Suzuki–Miyaura coupling as a key step and determination of the absolute configuration of natural products

  摘要：

  A versatile methodology for the synthesis of various terpenoids via B-alkyl Suzuki-Miyaura coupling as a key step is established. Synthesis of cordiaquinone J and K, new antifungal and larvicidal meroterpenoids, was achieved by using this methodology. The absolute configurations of cordiaquinone J and K were confirmed by the synthesis. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.06.115

文献信息

• Synthesis and absolute configuration of cordiaquinone K, antifungal and larvicidal meroterpenoid isolated from the Panamanian plant, Cordia curassavica
  作者：Arata Yajima、Fumihiro Saitou、Mayu Sekimoto、Shoichiro Maetoko、Goro Yabuta

  DOI：10.1016/s0040-4039(03)01669-1

  日期：2003.9

  Total synthesis of cordiaquinone K, a new antifungal and larvicidal meroterpenoid, is reported. The absolute configuration of cordiaquinone K was confirmed by the synthesis. (C) 2003 Elsevier Ltd. All rights reserved.