(2S,3E)-5-(tert-butyl(diphenyl)silyloxy)-4-methylpent-3-en-2-ol | 851626-19-2

• 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: (2S,3E)-5-(tert-butyl(diphenyl)silyloxy)-4-methylpent-3-en-2-ol
• 英文别名: (S,E)-5-(tert-butyldiphenylsilyloxy)-4-methylpent-3-en-2-ol；(E,2S)-5-[tert-butyl(diphenyl)silyl]oxy-4-methylpent-3-en-2-ol
• CAS: 851626-19-2
• 化学式: C₂₂H₃₀O₂Si
• 分子量: 354.565
• InChiKey: ZGOWYGGZBNGPSJ-YMIFCHIISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.89
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  (2S,3E)-5-(tert-butyl(diphenyl)silyloxy)-4-methylpent-3-en-2-ol 在 C₃₂H₁₂BF₂₄^(1-)*C₃₇H₅₂IrN₃O⁽¹⁺⁾ 、 氢气 作用下， 25.0 ℃ 、5.0 MPa 条件下， 反应 4.0h， 生成
  参考文献：
  名称：

  Asymmetric Hydrogenation Approaches to Valuable, Acyclic 1,3-Hydroxymethyl Chirons

  摘要：

  An iridium carbene oxazoline complex was used to catalyze hydrogenations of trisubstituted alkenes to give terminal and internal 1,3-hydroxymethyl chirons. The products are accessible in all possible stereoisomeric forms. These hydrogenation do not require strongly coordinating functionalities on the substrate, and in some key cases, catalyst-rather than substrate-controlled stereoselectives are observed. It is hypothesized that these reactions would not be feasible using iridium or rhodium diphosphind complexes.

  DOI：

  10.1021/ja802909b
• 作为产物：
  描述：

  (4S,2E)-ethyl 4-hydroxy-2-methylpent-2-enoate 在 咪唑 、 二异丁基氢化铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 13.17h， 生成 (2S,3E)-5-(tert-butyl(diphenyl)silyloxy)-4-methylpent-3-en-2-ol
  参考文献：
  名称：

  Highly enantioselective sequential Claisen–Ireland/metathesis: synthesis of cycloalkenes bearing two contiguous highly functionalized asymmetric centres

  摘要：

  A sequence of two reactions, consisting of a highly stereoselective silylated ketene acetal Claisen-Ireland rearrangement followed by a ring closing metathesis, gave a stereocontrolled access to various carbocycles. (C) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2004.12.029

文献信息

• Asymmetric Synthesis of (+)-Geranyllinaloisocyanide: Assignment of Absolute Stereochemistry
  作者：Yoshiyasu Ichikawa、Yasunori Matsuda、Ken Okumura、Mitsuhiro Nakamura、Toshiya Masuda、Hiyoshizo Kotsuki、Keiji Nakano

  DOI：10.1021/ol200308m

  日期：2011.5.20

  The first nonracemic synthesis of (+)-geranyllinaloisocyanide, starting with (–)-lactic acid methyl ester, has been accomplished by exploiting a [3.3] sigmatropic rearrangement of allyl cyanate. The synthesis enables assignment of the S configuration of the C(3) isocyano substituted, quaternary stereogenic center in natural geranyllinaloisocyanide.

  以（-）-乳酸甲酯为原料的（+）-香叶烯基异氰酸酯的第一个非外消旋合成是通过利用[3.3]烯丙基氰酸酯的σ重排而完成的。合成使S配置的C（3）异氰基取代的，季生立体中心在自然geranyllinaloisocyanide中的分配。
• Diastereoselective Access to the Spirotetronate Subunit of the Quartromicins<b />
  作者：Olivier Bedel、Antoine Français、Arnaud Haudrechy

  DOI：10.1055/s-2005-872657

  日期：——

  The agalacto-spirotetronate B subunit of quartromicins was synthesized in a predictible manner, following the Claisen-­Ireland/metathesis approach (CIM strategy). Ene-yne ring-closure and selective mismatch Sharpless dihydroxylation are discussed as key steps, allowing an efficient approach to these structures.

  按照克来森-爱尔兰/甲基化方法（CIM 战略），以可预测的方式合成了喹诺酮类药物的琼脂糖螺环酯 B 亚基。讨论了作为关键步骤的炔-炔环闭和选择性错配夏普无二羟基化，从而有效地获得了这些结构。