(3S,4R)-3-(tert-butyldimethylsilyloxy)-4-methylhept-6-en-1-ol | 314273-41-1

• 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: (3S,4R)-3-(tert-butyldimethylsilyloxy)-4-methylhept-6-en-1-ol
• 英文别名: (3S,4R)-3-[tert-butyl(dimethyl)silyl]oxy-4-methylhept-6-en-1-ol
• CAS: 314273-41-1
• 化学式: C₁₄H₃₀O₂Si
• 分子量: 258.476
• InChiKey: QAXXMKJESBZQQM-OLZOCXBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.97
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3S,4R)-3-(tert-butyldimethylsilyloxy)-4-methylhept-6-en-1-ol 在 吡啶 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 17.5h， 生成
  参考文献：
  名称：

  Synthetic studies on the salicylihalamides: macrolactone formation via ring closing metathesis versus macrolactonization

  摘要：

  Two routes to the unusual 12-membered unsaturated benzolactone of the highly cytotoxic marine metabolites the salicylihalamides are presented. The first involves an RCM step to construct the C9-C10 alkene bond and this provided the model macrolactones 9 and 10 in a ratio of 77:23, respectively. An alternative route involved a Stille coupling to construct the C8-C9 bond followed by a macrolactonization to give the lactones 9 and 10 in a ratio of 96:4. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01420-9
• 作为产物：
  描述：

  在 吡啶 、 氢氟酸 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 (3S,4R)-3-(tert-butyldimethylsilyloxy)-4-methylhept-6-en-1-ol
  参考文献：
  名称：

  Synthetic studies on the salicylihalamides: macrolactone formation via ring closing metathesis versus macrolactonization

  摘要：

  Two routes to the unusual 12-membered unsaturated benzolactone of the highly cytotoxic marine metabolites the salicylihalamides are presented. The first involves an RCM step to construct the C9-C10 alkene bond and this provided the model macrolactones 9 and 10 in a ratio of 77:23, respectively. An alternative route involved a Stille coupling to construct the C8-C9 bond followed by a macrolactonization to give the lactones 9 and 10 in a ratio of 96:4. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01420-9

文献信息

• Gram scale synthesis of the C(1)–C(9) fragment of amphidinolide C
  作者：Nicholas A. Morra、Brian L. Pagenkopf

  DOI：10.1016/j.tet.2013.07.026

  日期：2013.10

  Subsequent manipulations, including a Still–Gennari olefination, Sharpless asymmetric dihydroxylation, Corey–Fuchs alkynylation, and Kazmaier hydrostannylation provided the fully functionalized C(1)–C(9) fragment 2 suitable for cross-coupling. The sequence is readily scalable and provides gram quantities of 2.

  通过关键的一个碳同源性，通过Sharpless不对称环氧化制备的烯丙基顺式环氧化物以九个步骤和41％的总产率转化为环化前体4。的钴催化的需氧氧化环4得到的反式，94％收率-THF在克规模。随后的操作，包括Still–Gennari烯化，Sharpless不对称二羟基化，Corey–Fuchs炔基化和Kazmaier加氢甲锡化，提供了适用于交叉偶联的完全官能化的C（1）–C（9）片段2。该序列易于扩展，并提供2的克数量。
• Synthetic studies on the salicylihalamides: macrolactone formation via ring closing metathesis versus macrolactonization
  作者：John T Feutrill、Georgina A Holloway、Ferdows Hilli、Helmut M Hügel、Mark A Rizzacasa

  DOI：10.1016/s0040-4039(00)01420-9

  日期：2000.10

  Two routes to the unusual 12-membered unsaturated benzolactone of the highly cytotoxic marine metabolites the salicylihalamides are presented. The first involves an RCM step to construct the C9-C10 alkene bond and this provided the model macrolactones 9 and 10 in a ratio of 77:23, respectively. An alternative route involved a Stille coupling to construct the C8-C9 bond followed by a macrolactonization to give the lactones 9 and 10 in a ratio of 96:4. (C) 2000 Elsevier Science Ltd. All rights reserved.