(1R,3R)-2-methylene-5-(prop-1-en-2-yl)cyclohexane-1,3-diol | 1418734-55-0

• 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: (1R,3R)-2-methylene-5-(prop-1-en-2-yl)cyclohexane-1,3-diol
• 英文别名: (1R)-2-methylene-5-(prop-1-en-2-yl)cyclohexane-1,3-diol；(1R,3R)-2-methylidene-5-prop-1-en-2-ylcyclohexane-1,3-diol
• CAS: 1418734-55-0
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: NHJVCWGYXCFQJJ-NXEZZACHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (1R,4R,6R)-4-isopropenyl-1-methyl-7-oxabicyclo[4.1.0]heptan-2-one 在 sodium tetrahydroborate 、 cerium(III) chloride 、 bis(cyclopentadienyl)titanium (III) chloride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.83h， 生成 (1R,5S)-香芹醇 、 (1R,3R)-2-methylene-5-(prop-1-en-2-yl)cyclohexane-1,3-diol
  参考文献：
  名称：

  Titanocene-promoted stereoselective eliminations on epoxy alcohols derived from R-(−)-carvone

  摘要：

  The reaction of several stereoisomeric epoxy alcohols, obtained from R-(-)-carvone, and their corresponding formates, acetates, and benzoates, promoted by Cp2TiCl has been studied. The different outcomes of the reaction of epoxy derivatives are rationalized in terms of mechanistically biased processes. The radicals emerging from oxirane cleavage provide two types of reaction: dehydroxylation (deoxy-carbonylation) and dehydrogenation.The results offer considerable support for the radical elimination theory of hydroxyl, formyloxyl, and acetoxyl groups. The inability of tertiary radicals to be reduced by the Ti(III) complex is demonstrated unequivocally. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.11.093

文献信息

• Non-natural Elemane as the “Stepping Stone” for the Synthesis of Germacrane and Guaiane Sesquiterpenes
  作者：Elissavet E. Anagnostaki、Alexandros L. Zografos

  DOI：10.1021/ol3031999

  日期：2013.1.4

  utilization as a common synthetic scaffold to produce structurally diverse germacrane and guaiane sesquiterpenes are described. A highly enantio- and stereoselective biomimetic tandem oxy-Cope/ene rearrangement was used as the key reaction to access the 10-membered macrocyclic core of germacranes and the condensed 5–7 carbocycles of guaiane sesquiterpenes. Additionally, reactions of furanoguaianes under acidic

  描述了由（R）-香芹酮合成羟基elemane 5以及将其用作生产结构上不同的germ草和愈创树倍半萜的普通合成支架。高度对映体和立体选择性的仿生串联氧代-Cope /烯重排反应被用作关键反应，以接近10员额的大环戊烷和缩影的愈创树倍半萜的5-7个碳环。另外，已经研究了呋喃并呋喃酮在酸性或氧化剂下的反应，并给出了这些转化的初步结果。