tert-Butyl-[(Z)-(S)-(R)-1-(1,4-dioxa-spiro[4.5]dec-2-yl)-non-3-enyloxy]-dimethyl-silane | 180986-86-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-Butyl-[(Z)-(S)-(R)-1-(1,4-dioxa-spiro[4.5]dec-2-yl)-non-3-enyloxy]-dimethyl-silane
• 英文别名: tert-butyl-[(Z,1S)-1-[(3R)-1,4-dioxaspiro[4.5]decan-3-yl]non-3-enoxy]-dimethylsilane
• CAS: 180986-86-1
• 化学式: C₂₃H₄₄O₃Si
• 分子量: 396.686
• InChiKey: KYPMONZRLRAUOZ-BBRGTYKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.98
• 重原子数：
  27
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-Butyl-[(Z)-(S)-(R)-1-(1,4-dioxa-spiro[4.5]dec-2-yl)-non-3-enyloxy]-dimethyl-silane 在 sodium periodate 、 三氟乙酸 作用下， 以 水 、 乙腈 为溶剂， 反应 6.0h， 生成 (Z,2S)-2-[tert-butyl(dimethyl)silyl]oxydec-4-enal
  参考文献：
  名称：

  (R)-2,3-O-Cyclohexylideneglyceraldehyde, a Versatile Intermediate for Asymmetric Synthesis of Homoallyl and Homopropargyl Alcohols in Aqueous Medium

  摘要：

  Zn-mediated allylation and propargylation of (R)-2,3-O-cyclohexylideneglyceraldehyde (1) in aqueous medium following Luche's procedure afforded the anti homoallylic 3 and homopropargylic 8 alcohols in good yield and with high stereoselectivity, Crotylation of 1 under similar conditions afforded appreciable amounts of erythro-5 and threo-6 alcohols. In each case, the diastereo alcohols are separable by column chromatography. Compound 8 on appropriate chemical manipulation of its functionalities gave the (S)-enantiomer of (R)-13, a useful synthon of LTB(4). Compound 3 on chemical elaboration afforded a diversely functionalized triol derivative 15, a potentially useful synthon for many bioactive compounds.

  DOI：

  10.1021/jo9604696
• 作为产物：
  描述：

  (R)-1,4-二氧杂螺[4,5]癸烷-2-甲醛 在 P⁽²⁾-Ni 咪唑 、 正丁基锂 、 氢气 、 氯化铵 、 锌 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 tert-Butyl-[(Z)-(S)-(R)-1-(1,4-dioxa-spiro[4.5]dec-2-yl)-non-3-enyloxy]-dimethyl-silane
  参考文献：
  名称：

  (R)-2,3-O-Cyclohexylideneglyceraldehyde, a Versatile Intermediate for Asymmetric Synthesis of Homoallyl and Homopropargyl Alcohols in Aqueous Medium

  摘要：

  Zn-mediated allylation and propargylation of (R)-2,3-O-cyclohexylideneglyceraldehyde (1) in aqueous medium following Luche's procedure afforded the anti homoallylic 3 and homopropargylic 8 alcohols in good yield and with high stereoselectivity, Crotylation of 1 under similar conditions afforded appreciable amounts of erythro-5 and threo-6 alcohols. In each case, the diastereo alcohols are separable by column chromatography. Compound 8 on appropriate chemical manipulation of its functionalities gave the (S)-enantiomer of (R)-13, a useful synthon of LTB(4). Compound 3 on chemical elaboration afforded a diversely functionalized triol derivative 15, a potentially useful synthon for many bioactive compounds.

  DOI：

  10.1021/jo9604696

文献信息

• (<i>R</i>)-2,3-<i>O</i>-Cyclohexylideneglyceraldehyde, a Versatile Intermediate for Asymmetric Synthesis of Homoallyl and Homopropargyl Alcohols in Aqueous Medium
  作者：Angshuman Chattopadhyay

  DOI：10.1021/jo9604696

  日期：1996.1.1

  Zn-mediated allylation and propargylation of (R)-2,3-O-cyclohexylideneglyceraldehyde (1) in aqueous medium following Luche's procedure afforded the anti homoallylic 3 and homopropargylic 8 alcohols in good yield and with high stereoselectivity, Crotylation of 1 under similar conditions afforded appreciable amounts of erythro-5 and threo-6 alcohols. In each case, the diastereo alcohols are separable by column chromatography. Compound 8 on appropriate chemical manipulation of its functionalities gave the (S)-enantiomer of (R)-13, a useful synthon of LTB(4). Compound 3 on chemical elaboration afforded a diversely functionalized triol derivative 15, a potentially useful synthon for many bioactive compounds.