(3R,4R)-2,2-dimethyl-4-methoxy-5-hexen-3-ol | 1161746-19-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R,4R)-2,2-dimethyl-4-methoxy-5-hexen-3-ol
• 英文别名: (3R,4R)-4-methoxy-2,2-dimethylhex-5-en-3-ol
• CAS: 1161746-19-5
• 化学式: C₉H₁₈O₂
• 分子量: 158.241
• InChiKey: DGJKIRZSESDADY-SFYZADRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  ((1S,5S,10R)-9-(((3R,4R)-4-methoxy-2,2-dimethylhex-5-en-3-yl)oxy)-9-borabicyclo[3.3.2]decan-10-yl)trimethylsilane 、 左旋伪麻黄碱 以 乙腈 为溶剂， 反应 12.0h， 生成 9-(1R,2R-pseudoephedrinyl)-10S-trimethylsilyl-9-borabicyclo[3.3.2]decane 、 (3R,4R)-2,2-dimethyl-4-methoxy-5-hexen-3-ol
  参考文献：
  名称：

  Asymmetric γ-Methoxyallylation with the Robust 10-TMS-9-Borabicyclo[3.3.2]decanes

  摘要：

  The asymmetric gamma-methoxyallylboration of aldehydes with the configurationally very stable 1 gives nonracemic threo-beta-methoxyhomoallylic alcohols 7 (65-93%) with excellent selectivity (96-99% de, 98-99% ee). The corresponding homoallylic amines 10 are obtained from N-H aldimines with similar efficiency (72-96%) and with excellent diastereoselectivity (98% de) but with lower enantioselectivity (56-86% ee). These new reagents provide ready access to a Taxol side chain derivative.

  DOI：

  10.1021/ol900865y

文献信息

• A Variant of the Takai−Utimoto Reaction of Acrolein Acetals with Aldehydes Catalytic in Chromium:  A Highly Stereoselective Route to Anti Diol Derivatives
  作者：Robert K. Boeckman,、Raymond A. Hudack

  DOI：10.1021/jo980160h

  日期：1998.5.1
• Asymmetric γ-Methoxyallylation with the Robust 10-TMS-9-Borabicyclo[3.3.2]decanes
  作者：Lorell Muñoz-Hernández、John A. Soderquist

  DOI：10.1021/ol900865y

  日期：2009.6.18

  The asymmetric gamma-methoxyallylboration of aldehydes with the configurationally very stable 1 gives nonracemic threo-beta-methoxyhomoallylic alcohols 7 (65-93%) with excellent selectivity (96-99% de, 98-99% ee). The corresponding homoallylic amines 10 are obtained from N-H aldimines with similar efficiency (72-96%) and with excellent diastereoselectivity (98% de) but with lower enantioselectivity (56-86% ee). These new reagents provide ready access to a Taxol side chain derivative.