(1S,2R,5R,7S,9R)-5-acetyl-10,10-dimethyl-4,6-dioxatricyclo[7.1.1.0^2,7]undecane | 1004540-76-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S,2R,5R,7S,9R)-5-acetyl-10,10-dimethyl-4,6-dioxatricyclo[7.1.1.0^2,7]undecane
• 英文别名: 1-[(1S,2R,5R,7S,9R)-10,10-dimethyl-4,6-dioxatricyclo[7.1.1.02,7]undecan-5-yl]ethanone
• CAS: 1004540-76-4
• 化学式: C₁₃H₂₀O₃
• 分子量: 224.3
• InChiKey: RHAGBKCDDBQLRA-WTPMCQDGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,2R,5R,7S,9R)-5-acetyl-10,10-dimethyl-4,6-dioxatricyclo[7.1.1.0^2,7]undecane 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 (1S,2R,5R,7S,9R,1'S)-5-(1'-hydroxyethyl)-10,10-dimethyl-4,6-dioxatricyclo[7.1.1.0^2,7]undecane 、 (1S,2R,5R,7S,9R,1'R)-5-(1'-hydroxyethyl)-10,10-dimethyl-4,6-dioxatricyclo[7.1.1.0^2,7]undecane
  参考文献：
  名称：

  New 2-acyl-1,3-dioxane derivatives from (1R)-(−)-myrtenal: stereochemical effect on their relative ability as chiral auxiliaries

  摘要：

  Four 3,10-pinanediol derivatives 1a-d, prepared in 50-72% global yields from (IR)-(-)-myrtenal 2, were treated with (RO)(2)CHCOR3 (R-3 = CH3, Ph) to afford 2-acyl-1,3-dioxanes 3a-f. The latter were submitted to nucleophilic additions using several Grignard reagents to mainly afford carbinols generated by re diastereofacial attack (85-99% yield, >= 88:12 dr). The lowest diastereoselectivity was observed when PhLi or hydrides were used as nucleophiles. Only an equatorial substituent at C-3 modifies the diastereoselectivity of the nucleophilic additions. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.10.047
• 作为产物：
  描述：

  1,1-二甲氧基丙酮 、 (1S,2R,3S)-2-hydroxymethyl-6,6-dimethylbicyclo[3.1.1]heptan-3-ol 在 camphor-10-sulfonic acid 作用下， 以 四氯化碳 、 苯 为溶剂， 反应 72.0h， 以54%的产率得到(1S,2R,5R,7S,9R)-5-acetyl-10,10-dimethyl-4,6-dioxatricyclo[7.1.1.0^2,7]undecane
  参考文献：
  名称：

  New 2-acyl-1,3-dioxane derivatives from (1R)-(−)-myrtenal: stereochemical effect on their relative ability as chiral auxiliaries

  摘要：

  Four 3,10-pinanediol derivatives 1a-d, prepared in 50-72% global yields from (IR)-(-)-myrtenal 2, were treated with (RO)(2)CHCOR3 (R-3 = CH3, Ph) to afford 2-acyl-1,3-dioxanes 3a-f. The latter were submitted to nucleophilic additions using several Grignard reagents to mainly afford carbinols generated by re diastereofacial attack (85-99% yield, >= 88:12 dr). The lowest diastereoselectivity was observed when PhLi or hydrides were used as nucleophiles. Only an equatorial substituent at C-3 modifies the diastereoselectivity of the nucleophilic additions. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.10.047

文献信息

• New 2-acyl-1,3-dioxane derivatives from (1R)-(−)-myrtenal: stereochemical effect on their relative ability as chiral auxiliaries
  作者：Elvia Becerra-Martínez、Pedro Velázquez-Ponce、Miguel A. Sánchez-Aguilar、Alfredo Rodríguez-Hosteguín、Pedro Joseph-Nathan、Joaquín Tamariz、L. Gerardo Zepeda

  DOI：10.1016/j.tetasy.2007.10.047

  日期：2007.11

  Four 3,10-pinanediol derivatives 1a-d, prepared in 50-72% global yields from (IR)-(-)-myrtenal 2, were treated with (RO)(2)CHCOR3 (R-3 = CH3, Ph) to afford 2-acyl-1,3-dioxanes 3a-f. The latter were submitted to nucleophilic additions using several Grignard reagents to mainly afford carbinols generated by re diastereofacial attack (85-99% yield, >= 88:12 dr). The lowest diastereoselectivity was observed when PhLi or hydrides were used as nucleophiles. Only an equatorial substituent at C-3 modifies the diastereoselectivity of the nucleophilic additions. (c) 2007 Elsevier Ltd. All rights reserved.