(1S,2R,3S,10S)-2-(1-hydroxyethyl)-6,6-dimethylbicyclo[3.1.1]heptan-3-ol | 1004540-73-1

• 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,3S,10S)-2-(1-hydroxyethyl)-6,6-dimethylbicyclo[3.1.1]heptan-3-ol
• 英文别名: (1S,2R,3S,5R)-2-[(1S)-1-hydroxyethyl]-6,6-dimethylbicyclo[3.1.1]heptan-3-ol
• CAS: 1004540-73-1
• 化学式: C₁₁H₂₀O₂
• 分子量: 184.279
• InChiKey: QFVDXAZHYHETRC-SVSWQMSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,2R,3S,10S)-2-(1-hydroxyethyl)-6,6-dimethylbicyclo[3.1.1]heptan-3-ol 、 alkaline earth salt of/the/ methylsulfuric acid 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 3.5h， 以50%的产率得到(1S,2R,3S,5R,7S,9R)-5-benzoyl-3,10,10-trimethyl-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-((1R,5S)-6,6-dimethylbicyclo[3.1.1]hept-2-en-2-yl)ethan-1-ol 在 tetrafluoroboric acid-diethyl ether complex 、 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 28.5h， 以50%的产率得到(1S,2R,3S,10S)-2-(1-hydroxyethyl)-6,6-dimethylbicyclo[3.1.1]heptan-3-ol
  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

• Diastereoselective Preparation of (<i>R</i>)- and (<i>S</i>)-2-Methoxy-2-phenylpent-3-ynoic Acids and Their Use as Reliable Chiral Derivatizing Agents
  作者：Salvador Pérez-Estrada、Pedro Joseph-Nathan、Hugo A. Jiménez-Vázquez、Manuel E. Medina-López、Francisco Ayala-Mata、L. Gerardo Zepeda

  DOI：10.1021/jo2016554

  日期：2012.2.17

  O-acetals 1a and 1b were used as chiral auxiliaries to achieve the diastereoselective preparation of both enantiomers of 2-methoxy-2-phenylpent-3-ynoic acids (MPPAs). The latter were condensed with several chiral secondary alcohols and some primary amines to evaluate their potential as chiral derivatizing agents (CDAs). The 1H NMR spectra of the corresponding esters and amides showed strong consistency with

  苯甲酰基-S，O-乙缩醛1a和1b用作手性助剂，以实现非对映选择性制备2-甲氧基-2-苯基戊-3-炔酸（MPPAs）的两种对映体。后者与几种手性仲醇和一些伯胺缩合，以评估其作为手性衍生剂（CDA）的潜力。的1个对应的酯和酰胺的1 H NMR光谱显示出很强的一致性与甲醇和胺部分，其观察到的ΔδL的绝对构型1和ΔδL 2个值分别为在0.1-0.4和0.02-0.12 ppm的范围。