(1RS,2SR,3SR)-2-(hydroxymethyl-2,3-dimethylcyclohexyl)methanol | 98540-11-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1RS,2SR,3SR)-2-(hydroxymethyl-2,3-dimethylcyclohexyl)methanol
• 英文别名: (+/-)-[(1R,2S,6S)-1,6-dimethylcyclohexane-1,2-diyl]dimethanol；[(1S,2R,3S)-2-(hydroxymethyl)-2,3-dimethylcyclohexyl]methanol
• CAS: 98540-11-5；122518-92-7
• 化学式: C₁₀H₂₀O₂
• 分子量: 172.268
• InChiKey: HMBUCIKWQGVOJJ-IVZWLZJFSA-N

物化性质

• 沸点：
  264.1±8.0 °C(Predicted)
• 密度：
  0.946±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  2
• 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：

  (1RS,2SR,3SR)-2-(hydroxymethyl-2,3-dimethylcyclohexyl)methanol 在 碘代三甲硅烷 、 lithium hexamethyldisilazane 作用下， 以 六甲基磷酰三胺 、 乙二醇二甲醚 、 氯仿 为溶剂， 生成 (3aR,4S,7aR)-2-[1-(tert-Butyl-dimethyl-silanyloxymethyl)-vinyl]-3a,4-dimethyl-octahydro-indene-2-carboxylic acid methyl ester
  参考文献：
  名称：

  （+）-bakkenolide-A的对映体全合成

  摘要：

  从（S）-1,6-二甲基-1-环己烯可以有效地，立体选择性地合成天然巴克诺德内酯A，该化合物可从2-甲基-2-环己烯-1-酮中以3种高收率获得脚步。

  DOI：

  10.1016/s0040-4039(00)80838-2
• 作为产物：
  描述：

  (+/-)-{(1R,2S,6S)-2-[(benzyloxy)methyl]-1,6-dimethylcyclohex-3-en-1-yl}methanol 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以99%的产率得到(1RS,2SR,3SR)-2-(hydroxymethyl-2,3-dimethylcyclohexyl)methanol
  参考文献：
  名称：

  Core Structure of Eremophilanes and Bakkanes through Niobium Catalyzed Diels−Alder Reaction:  Synthesis of (±)-Bakkenolide A

  摘要：

  A suitable intermediate for the synthesis of eremophilanes and bakkanes was prepared by a highly regioselective and stereoselective one-step synthesis through a niobium catalyzed Diels-Alder reaction. As a demonstration of the versatility of this intermediate, a total synthesis of (+)-bakkenolide A is described.

  DOI：

  10.1021/jo061722x

文献信息

• First Comprehensive Bakkane Approach:  Stereoselective and Efficient Dichloroketene-Based Total Syntheses of (±)- and (−)-9-Acetoxyfukinanolide, (±)- and (+)-Bakkenolide A, (−)-Bakkenolides III, B, C, H, L, V, and X, (±)- and (−)-Homogynolide A, (±)-Homogynolide B, and (±)-Palmosalide C
  作者：Timothy J. Brocksom、Fernando Coelho、Jean-Pierre Deprés、Andrew E. Greene、Marco E. Freire de Lima、Olivier Hamelin、Benoît Hartmann、Alice M. Kanazawa、Yanyun Wang

  DOI：10.1021/ja0208456

  日期：2002.12.1

  dichloroketene with dimethylcyclohexenes has been used as the key reaction in an efficient, general approach to the bakkanes. New methods and methodologies that have been developed in this work include spiro beta-methylene-gamma-butyrolactonizations, a vicinal dicarboxylation, an angelic ester preparation, a transesterification, an epoxy ketone double reduction, and a retro aldol-aldol approach to low-energy aldol

  二氯乙烯酮与二甲基环己烯的环加成反应已被用作一种有效、通用的巴卡内酯方法中的关键反应。在这项工作中开发的新方法和方法包括螺β-亚甲基-γ-丁内酯化、邻位二羧化、当归酯制备、酯交换、环氧酮双还原和低能量的逆羟醛-羟醛方法醛醇异构体。
• An approach to the bakkanes. A short, stereocontrolled total synthesis of (.+-.)-bakkenolide A
  作者：Andrew E. Greene、Jean Pierre Depres、Fernando Coelho、Timothy J. Brocksom

  DOI：10.1021/jo00220a060

  日期：1985.10
• Regiocontrol of Radical Cyclization by Lewis Acids. Efficient Synthesis of Optically Active Functionalized Cyclopentanes and Cyclohexanes
  作者：Kwangho Kim、Sentaro Okamoto、Fumie Sato

  DOI：10.1021/ol0067890

  日期：2001.1.1

  [GRAPHICS]Treatment of alpha -alkylidenelactones 3a-d with Bu3SnH and a catalytic amount of Et3B effected a 5-exo radical cyclization preferentially to provide the corresponding 1 and 2 in a ratio of 70:30 to 100:0, Meanwhile, the reaction of 3a and 3b in the presence of Et2AlCl proceeded via a B-endo cyclization pathway predominantly to afford 2a and 2b with 90% and 92% regioselectivity, respectively.
• GREENE, ANDREW E.;COELHO, FERNANDO;DEPRES, JEAN-PIERRE;BROCKSOM, TIMOTHY +, TETRAHEDRON LETT., 29,(1988) N 44, C. 5661-5662
  作者：GREENE, ANDREW E.、COELHO, FERNANDO、DEPRES, JEAN-PIERRE、BROCKSOM, TIMOTHY +

  DOI：——

  日期：——