trans-2-Decen-1-ol, tert-butyldimethylsilyl ether | 83026-86-2

• 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: trans-2-Decen-1-ol, tert-butyldimethylsilyl ether
• 英文别名: tert-butyl-[(E)-dec-2-enoxy]-dimethylsilane
• CAS: 83026-86-2
• 化学式: C₁₆H₃₄OSi
• 分子量: 270.531
• InChiKey: YILLTVJAPOCBAB-BUHFOSPRSA-N

物化性质

• 保留指数：
  1604.3

计算性质

• 辛醇/水分配系数(LogP)：
  5.92
• 重原子数：
  18
• 可旋转键数：
  10
• 环数：
  0.0
• 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：

  trans-2-Decen-1-ol, tert-butyldimethylsilyl ether 在 盐酸 、 甲基磺酰胺 、 AD-mix-β 、 溴 、 potassium carbonate 、 对甲苯磺酸 、 三苯基膦 作用下， 以 乙醇 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 97.5h， 生成 (2R,3R)-1,2-epoxy-3-decanol
  参考文献：
  名称：

  Straightforward Synthesis of Panaxytriol:  An Active Component of Red Ginseng

  摘要：

  A total synthesis of (3R,9R,10R)-panaxytriol (1) was accomplished enantioselectively (40% overall yield; 30% for the longest sequence). A key step was a Cadiot-Chodkiewicz cross-coupling reaction on two fragments containing, in the aggregate, three unprotected hydroxyl groups. One fragment was synthesized by a highly enantioselective reduction of an enynone. The other arose from a highly enantioselective dihydroxylation of an allylic alcohol.

  DOI：

  10.1021/jo0341665
• 作为产物：
  描述：

  反式-2-癸烯醇 、 叔丁基二甲基氯硅烷 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 trans-2-Decen-1-ol, tert-butyldimethylsilyl ether
  参考文献：
  名称：

  An Access to erythro-Diols via Sharpless's Asymmetric Dihydroxylation Reaction

  摘要：

  A method has been developed to access erythro-2,3-diols via Sharpless's asymmetric dihydroxylation reaction. Thus, a TBDMS-protected (E)-allylic alcohol is dihydroxylated and the resulting threo-2,3-diol is converted to the cyclic sulfate. Upon desilylation, this compound undergoes a Payne-type rearrangement. Nucleophilic epoxide-opening then provides an erythro-2,3-diol. The conversions from the cyclic sulfate to the diol product are performed in a single reaction vessel. Due to the irreversible nature of the Payne-type rearrangement, this process is easy to perform and completely regioselective independent of the substrate structures. Also, being performed in THF, the process is compatible with a variety of nucleophiles, including thiolates, N--(3), (OAc)-O--, (CN)-C--, halides as well as carbon nucleophiles and hydride.

  DOI：

  10.1021/jo00088a045

文献信息

• γ-Selective allylic substitution reaction with Grignard reagents catalyzed by copper N -heterocyclic carbene complexes and its application to enantioselective synthesis
  作者：Satoshi Tominaga、Yukinao Oi、Toshio Kato、Duk Keun An、Sentaro Okamoto

  DOI：10.1016/j.tetlet.2004.05.135

  日期：2004.7

  The reaction of allylic compounds with alkyl Grignard reagents in the presence of a catalytic amount of copper N-heterocyclic carbene (NHC) complexes proceeded predominantly in an SN2′ reaction pathway to give γ-substituted product in excellent yield. The method was applied to asymmetric reaction by using optically active NHC ligands.

  烯丙基化合物与在铜催化量的存在下烷基格氏试剂反应ñ -杂环卡宾（NHC）络合物在一个S主要进行Ñ的优良率2'的反应途径，得到γ-取代的产物。该方法通过使用旋光性NHC配体用于不对称反应。
• An Access to erythro-Diols via Sharpless's Asymmetric Dihydroxylation Reaction
  作者：Soo Y. Ko、Majbeen Malik、A. Frances Dickinson

  DOI：10.1021/jo00088a045

  日期：1994.5

  A method has been developed to access erythro-2,3-diols via Sharpless's asymmetric dihydroxylation reaction. Thus, a TBDMS-protected (E)-allylic alcohol is dihydroxylated and the resulting threo-2,3-diol is converted to the cyclic sulfate. Upon desilylation, this compound undergoes a Payne-type rearrangement. Nucleophilic epoxide-opening then provides an erythro-2,3-diol. The conversions from the cyclic sulfate to the diol product are performed in a single reaction vessel. Due to the irreversible nature of the Payne-type rearrangement, this process is easy to perform and completely regioselective independent of the substrate structures. Also, being performed in THF, the process is compatible with a variety of nucleophiles, including thiolates, N--(3), (OAc)-O--, (CN)-C--, halides as well as carbon nucleophiles and hydride.
• Ko Soo Y., Malik Majbeen, Dickinson A. Frances, J. Org. Chem, 59 (1994) N 9, S 2570-2576
  作者：Ko Soo Y., Malik Majbeen, Dickinson A. Frances

  DOI：——

  日期：——
• HUTCHINS, R. O.;LEARN, K., J. ORG. CHEM., 1982, 47, N 22, 4380-4382
  作者：HUTCHINS, R. O.、LEARN, K.

  DOI：——

  日期：——
• Straightforward Synthesis of Panaxytriol:  An Active Component of Red Ginseng
  作者：Heedong Yun、Samuel J. Danishefsky

  DOI：10.1021/jo0341665

  日期：2003.5.1

  A total synthesis of (3R,9R,10R)-panaxytriol (1) was accomplished enantioselectively (40% overall yield; 30% for the longest sequence). A key step was a Cadiot-Chodkiewicz cross-coupling reaction on two fragments containing, in the aggregate, three unprotected hydroxyl groups. One fragment was synthesized by a highly enantioselective reduction of an enynone. The other arose from a highly enantioselective dihydroxylation of an allylic alcohol.