(R)-1-Cyclohexyl-propane-1,3-diol | 132921-97-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-1-Cyclohexyl-propane-1,3-diol
• 英文别名: (1R)-1-cyclohexylpropane-1,3-diol
• CAS: 132921-97-2
• 化学式: C₉H₁₈O₂
• 分子量: 158.241
• InChiKey: ZBJDOGKUWVTDQA-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• 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：

  (R)-1-Cyclohexyl-propane-1,3-diol 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 以92%的产率得到(R)-3-(tert-butyldimethylsilyloxy)-1-cyclohexylpropan-1-ol
  参考文献：
  名称：

  Symmetric Macrocycles by a Prins Dimerization and Macrocyclization Strategy

  摘要：

  A tandem dimerization/macrocyclization reaction utilizing the Prins cyclization has been developed. This reaction develops molecular complexity through the formation of highly substituted dimeric tetrahydropyran macrocycles. Mild conditions utilizing rhenium(VII) catalysts were explored for aromatic substrates, while harsher Lewis acidic conditions were used for aliphatic substrates. Both aldehydes and acetals are shown to be viable substrates for this reaction.

  DOI：

  10.1021/ol9022062
• 作为产物：
  描述：

  (2S,3S)-2-Bromo-3-cyclohexyl-3-hydroxy-propionic acid tert-butyl ester 在 lithium aluminium tetrahydride 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 0.5h， 生成 (R)-1-Cyclohexyl-propane-1,3-diol
  参考文献：
  名称：

  Highly enantioselective routes to darzens and acetate aldol products from achiral aldehydes and t-butyl bromoacetate

  摘要：

  New methodology is described for the enantioselective coupling of t-butyl bromoacetate with aldehydes to give anti-alpha-bromo beta-hydroxy esters (1), useful precursors of chiral glycidic esters (2), acetate aldols (3), beta-amino acid esters (4) and alpha-amino acid esters (5).

  DOI：

  10.1016/0040-4039(91)80631-f

文献信息

• Enantioselective Iridium-Catalyzed Vinylogous Reformatsky-Aldol Reaction from the Alcohol Oxidation Level: Linear Regioselectivity by Way of Carbon-Bound Enolates
  作者：Abbas Hassan、Jason R. Zbieg、Michael J. Krische

  DOI：10.1002/anie.201100646

  日期：2011.4.4

  Reformatsky reinvented: Highly enantioselective vinylogous Reformatsky‐type addition has been achieved from the alcohol oxidation level with linear regioselectivity through carbon‐bound enolates (see scheme; Boc=tert‐butoxycarbonyl). Complete levels of catalyst‐directed diastereoselectivity are observed in the reaction of an α‐chiral alcohol.

  Reformatsky 重新发明：高度对映选择性插烯 Reformatsky 型加成是通过碳键烯醇化物从醇氧化水平实现的，具有线性区域选择性（参见方案；Boc=叔丁氧基羰基）。在 α-手性醇的反应中观察到完全水平的催化剂导向的非对映选择性。
• Synthesis of <i>trans</i>-3,4-Dimethyl-4-(3-hydroxyphenyl)piperidine Opioid Antagonists:  Application of the <i>Cis</i>-Thermal Elimination of Carbonates to Alkaloid Synthesis
  作者：John A. Werner、Louis R. Cerbone、Scott A. Frank、Jeffrey A. Ward、Parviz Labib、Roger W. Tharp-Taylor、C. W. Ryan

  DOI：10.1021/jo951403y

  日期：1996.1.1

  Improved syntheses of two trans-3,4-dimethyl-4-(3-hydroxyphenyl)piperidine opioid antagonists from 1,3-dimethyl-4-piperidinone are described. The 1,3 dimethyl-4-arylpiperidinol 23 was selectively dehydrated in a two step process to the 1,3-dimethyl-4-aryl-1,2,3,6-tetrahydropyrodome 26 by the cis-thermal elimination of the corresponding alkyl carbonate derivative at 190 degrees C. In the presence of a basic nitrogen, the success of the elimination was found to be critically dependent upon the nature of the carbonate alkyl group, with Et, i-Bu, and i-Pr being preferred (90% yield). Alkylation of the metalloenamine, formed by deprotonation of 26 with n-BuLi, proceeded regio- and stereospecifically to give the trans-3,4-dimethyl-4-aryl-1,2,3,4-tetrahydrpyridine 27, which was converted in three steps to the common intermediate, (3R,4R)-3,4-dimethyl-4-(3-hydroxyphenyl)-piperidine. LY255582, a centrally-active opioid antagonist, and LY246736-dihydrate, a peripherally-active opioid antagonist, were prepared from 1,3-dimethyl-4-piperidinone in 11.8% yield (8 steps) and 6.2% yield (12 steps), respectively.
• Regioselective reductive opening of 2,3-epoxy alcohol derivatives with lithium borohydride in a solid state
  作者：Keisuke Sugita、Makoto Onaka、Yusuke Izumi

  DOI：10.1016/s0040-4039(00)88517-2

  日期：1990.1

  2, 3-Epoxy alcohol derivatives were reduced regiospecifically with lithium borohydride in a solid state suspended in hexane to yield the corresponding C-3 opening products.