Bicyclo<4.3.1>decan-1-ol | 22516-95-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Bicyclo<4.3.1>decan-1-ol
• 英文别名: Bicyclo[4.3.1]decan-1-ol
• CAS: 22516-95-6
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: LJIRUNYFEYYYME-UHFFFAOYSA-N

物化性质

• 熔点：
  141-142 °C
• 沸点：
  239.6±8.0 °C(Predicted)
• 密度：
  1.027±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  Bicyclo<4.3.1>decan-1-ol 、 三氟乙酸酐 在 吡啶 作用下， 反应 1.5h， 以92%的产率得到bicyclo<4.3.1>dec-1-yl trifluoroacetate
  参考文献：
  名称：

  Solvolysis of 2-methylene bicyclic bridgehead derivatives: a model for gradual variation of .pi.-conjugation in carbocations

  摘要：

  The rates of solvolysis in ethanol or 80% ethanol at 25-degrees-C have been determined on 2-methylenebicyclo[2.2.2]oct-1-yl triflate (4a), 2-methylenebicyclo[3.2.1]oct-1-yl triflate (5a), 2-methylenebicyclo[3.2.2]non-1-yl mesylate (6a), 2-methylenebicyclo[3.3.1]non-1-yl mesylate (7a-OMs) and heptafluorobutyrate (7a-OHFB), 1-chloro-2-methylenebicyclo[4.2.2]decane (8a), 2-methylenebicyclo[4.3.1]dec-1-yl trifluoroacetate (9a), and 4-methylene-3-homoadamantyl heptafluorobutyrate (10a) and on their corresponding parent 1-bicycloalkyl and 3-homoadamantyl derivatives 4b-10b containing the respective leaving group. The rate ratios for 4a/4b, 5a/5b, 10a/10b, 6a/6b, 7a/7b, 8a/8b, and 9a/9b are 10(-3.9), 10(-1.9), 10(-1.1), 10(0.8), 10(0.9) (for mesylate), 10(-0.2), and 10(0.7), respectively. A plot of the logarithms of the rate ratios against olefinic strain energies of their corresponding unsubstituted bridgehead olefins shows that the smaller the olefinic strain energy, the greater the rate ratio, providing a methodology to gradually change the conjugative ability of bridgehead carbocations. The enhancement of allylic conjugation with increasing skeletal flexibility has been further verified by the enhanced solvolysis rate of (E)-2-ethylidenebicyclo[3.2.2]non-1-yl mesylate ((E)-6e) relative to 6a by a factor of 259. A similar study on much more rigid (E)-2-ethylidenebicyclo[2.2.2]oct-1-yl triflate ((E)-4e) gave a (E)-4e/4a rate ratio of 6.3. AM1 semiempirical molecular orbital calculations on pertinent 2-methylene and (E)-2-ethylidene bridgehead carbocations and corresponding hydrocarbons (L = hydrogen) also supported the increase in the conjugation with increasing skeletal flexibility. The solvolysis products were solely bridgehead substitution products, no indication for the formation of bridgehead olefin via an S(N)1' mechanism having been obtained.

  DOI：

  10.1021/jo00027a050
• 作为产物：
  描述：

  2-环庚烯-1-酮 在 tris(dibenzoylmethano)iron(III) samarium diiodide 、 氢溴酸 、 四氯化钛 、 sodium iodide 作用下， 以 四氢呋喃 、 正己烷 、 丙酮 为溶剂， 反应 14.0h， 生成 Bicyclo<4.3.1>decan-1-ol
  参考文献：
  名称：

  A facile synthesis of bicyclo[m.n.1]alkan-1-ols. Evidence for organosamarium intermediates in the samarium(II) iodide promoted intramolecular Barbier-type reaction

  摘要：

  Samarium(II) iodide (SmI2) has been successfully employed as a reductive coupling agent for the intramolecular Barbier-type synthesis of bicyclo[m.n.1]alkan-1-ols. Thus, a variety of 3-(omega-iodoalkyl)cycloalkanones, upon treatment with SmI2 and a catalytic quantity of iron complex in tetrahydrofuran (THF), provide the title compounds in excellent yields. The reaction is quite general for the construction of diverse bicyclic ring systems, including the highly strained bicyclo[2.1.1]hexan-1-ol. In addition to exploring the synthetic utility of this reaction, studies have been performed which provide insight on the mechanistic details of the SmI2-promoted intramolecular Barbier-type synthesis. Compelling evidence for the intermediacy of organosamarium species has thus been gathered.

  DOI：

  10.1021/jo00013a008

文献信息

• HETEROCYCLIC COMPOUND AND USE THEREOF
  申请人：KOIKE Tatsuki

  公开号：US20120059030A1

  公开（公告）日：2012-03-08

  The present invention provides a heterocycle derivative having a superior amyloid β production inhibitory activity and/or a superior γ-secretase modulation activity, and use thereof. A compound represented by the formula (I): wherein each symbol is as defined in the present specification, or a salt thereof.

  本发明提供了一种具有优越的淀粉样蛋白β产生抑制活性和/或优越的γ-分泌酶调节活性的杂环衍生物，以及其用途。一种由下式（I）表示的化合物： 其中每个符号如本说明书中所定义，或其盐。
• Studies on bicyclononanes. Part VII. Reactions of (1-bicyclo[3,3,1]-nonyl)methyl and related ions
  作者：S. H. Graham、D. A. Jonas

  DOI：10.1039/j39690000188

  日期：——

  The solvolyses of esters of 1-hydroxymethylbicyclononane, 5-hydroxymethylmethylenecyclo-octane, and 1-methyl-5-hydroxymethylcyclo-octene are described, together with the deaminations of the corresponding amines. The occurrence of 1,3-hydride shifts is reported, and the implications of the results, as regards the π-route to bicyclic molecules, are discussed.

  描述了1-羟甲基双环壬烷，5-羟甲基亚甲基环辛烷和1-甲基-5-羟甲基环辛烯的酯的溶剂化，以及相应的胺的脱氨基。报告了1，3-氢化物移位的发生，并且讨论了关于到双环分子的π-途径的结果的含义。
• FUSED TRIAZOLES FOR THE TREATMENT OR PROPHYLAXIS OF MILD COGNITIVE IMPAIRMENT
  申请人：Koike Tatsuki

  公开号：US20130178497A1

  公开（公告）日：2013-07-11

  The present invention provides a heterocycle derivative having a superior amyloid β production inhibitory activity and/or a superior γ-secretase modulation activity, and use thereof. A compound represented by the formula (I): wherein each symbol is as defined in the present specification, or a salt thereof.

  本发明提供了一种具有优异的淀粉样β产生抑制活性和/或优异的γ-分泌酶调节活性的杂环衍生物及其使用。化合物的公式(I)表示的化合物：其中每个符号如本说明书所定义，或其盐。
• US8822699B2
  申请人：——

  公开号：US8822699B2

  公开（公告）日：2014-09-02
• US8901309B2
  申请人：——

  公开号：US8901309B2

  公开（公告）日：2014-12-02