三环[2.2.1.03,5]庚烷-2-醇 | 695-04-5

• 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
• 中文名称: 三环[2.2.1.03,5]庚烷-2-醇
• 英文名称: 3-nortricyclanol
• 英文别名: tricyclo[2.2.1.0²⁶]heptan-3-ol；tricyclo[2.2.1.02,6]heptan-3-ol；3-hydroxynortricyclane；nortricyclen-2-ol；Nortricyclanol；nortricyclyl alcohol
• CAS: 695-04-5
• 化学式: C₇H₁₀O
• 分子量: 110.156
• InChiKey: OZMQKGXJENMAHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  4.0
• 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：

  三环[2.2.1.03,5]庚烷-2-醇 在 氢氧化钾 、 aluminum isopropoxide 、 一水合肼 、 1,3-丙二醇 作用下， 生成 三环(2.2.1.02,6)庚烷
  参考文献：
  名称：

  Energy Intake, Body Mass Index, Physical Activity, and the Colorectal Adenoma-Carcinoma Sequence

  摘要：

  Little is known about the precise relationship between energy intake, overweight, sedentary lifestyle, and steps in the colorectal adenoma-carcinoma pathway. We studied these parameters within a case-control study. Patients with adenomas < 10 mm (n = 154) or > 10 min (n = 208) were compared with polyp-free controls (n = 426) for determining factors associated with adenoma formation, i.e., observed for small and large adenomas, or with adenoma growth only. Colorectal cancer cases (n = 171) were compared with population controls (n = 309) to determine factors specific to the final stage, cancer. Exercise reduced the risk of cancer [odds ratio (OR) = 0.3, 95% confidence interval (CI) = 0.2-0.5 for high vs. low physical activity] but had little influence on adenomas. High energy intake increased the risk of cancer [OR for 5th vs. 1st quintile (OR5) = 1.6, 95% CI = 0.9-2.9, p = 0.02], but not of adenomas. High body mass index (BMI) significantly increased the risk of large adenomas (OR, = 2.1, 95% CI = 1.2-3.5, p = 0. 02 and OR5 = 1.7, 95% CI = 1.0-3.1, p = 0.25) for large and small adenomas vs. polyp-free controls. Neither height nor weight nor BMI influenced the risk of cancer. Results were unmodified when controlling for dietary risk factors and family history. Energy intake, a sedentary lifestyle, and high BMI were independently associated with a high risk of cancer use for large adenomas, which indicates an effect on promotion of colorectal tumors. These findings suggest that preventive advice regarding these factors should be provided, even late in life, to decrease the risk of colorectal cancer.

  DOI：

  10.1207/s15327914nc391_7
• 作为产物：
  描述：

  2,5-降冰片二烯 在 三氟化硼乙醚 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 10.0h， 生成 三环[2.2.1.03,5]庚烷-2-醇
  参考文献：
  名称：

  Nortricyclyl-norbornenyl 阳离子。同位素扰动和同位素加扰

  摘要：

  用氘同位素微扰法研究了由 3-降三环基或降冰片烯基前体形成的稳定碳正离子。来自两个碳的 /sup 13/C NMR 信号，如果快速相互转化的降冰片烯基结构之间存在平衡，预计将通过同位素扰动广泛分裂，仅显示小的、与温度无关的分裂。得出的结论是，可能存在最多约 1% 的平衡降冰片烯基离子。单一结构（具有广泛电荷离域的北三环基）足以代表阳离子。这通过 di-/sup 13/C 标记的阳离子前体进行了验证，该前体还提供了完整的 J/sub 12/ /sup 13/C-/sup 13/C 偶联常数。氘化离子和 1 的核磁共振谱，7-di/sup 13/C 标记的离子表明阳离子在 0/sup 0/C 以下经历至少三种不同的加扰过程。光谱显示最快的过程涉及到双环 (3.1.1) 庚烯基阳离子的可逆骨架重排。还发生更慢的过程，包括氢化物转变。观察到的重排最终导致阳离子中所有碳和氢的完全混乱。

  DOI：

  10.1021/ja00246a035

文献信息

• [EN] NOVEL COMPOUNDS<br/>[FR] NOUVEAUX COMPOSÉS
  申请人：GLAXOSMITHKLINE IP DEV LTD

  公开号：WO2015180612A1

  公开（公告）日：2015-12-03

  Disclosed are novel retinoid-related orphan receptor gamma (RORγ) modulators and their use in the treatment of diseases mediated by RORγ.

  揭示了新型视黄醇相关孤儿受体γ（RORγ）调节剂及其在通过RORγ介导的疾病治疗中的应用。
• Enantioselective Ring Opening of<i>meso</i>-Epoxides with Silicon Tetrachloride Catalyzed by Pyridine<i>N</i>-Oxides Fused with the Bicyclo[3.3.1]nonane Framework
  作者：Algirdas Neniškis、Sigitas Stončius

  DOI：10.1002/ejoc.201500762

  日期：2015.10

  chiral Lewis basic organocatalysts that contain pyridine N-oxide moieties fused with the bicyclo[3.3.1]nonane framework is reported. The obtained pyridine N-oxides were employed as catalysts in the enantioselective ring opening of meso-epoxides with silicon tetrachloride. Derivative 1b endowed with two 2,4-diaryl-substituted pyridine N-oxide moieties proved to be a particularly effective catalyst for desymmetrization

  报道了新的手性路易斯碱性有机催化剂的合成，该催化剂含有与双环 [3.3.1] 壬烷骨架稠合的吡啶 N-氧化物部分。所得吡啶N-氧化物用作中间环氧化物与四氯化硅对映选择性开环的催化剂。具有两个 2,4-二芳基取代的吡啶 N-氧化物部分的衍生物 1b 被证明是一种特别有效的催化剂，可用于降冰片烯氧化物 16i 的去对称化，以提供前所未有的 96% ee 的 Wagner-Meerwein 重排产物 20i。双功能同源物 3 带有 4-芳基取代基，与脂环族环氧化物底物表现出中等至高水平的不对称诱导（47-88% ee）。
• Action du N-bromosuccinimide sur les dioxolannes en série bicyclo [2.2.1 ]heptanique. Limitation des transpositions de wagner-meerwein
  作者：Akram Bazbouz、Henri Christol、Jacques Coste、Françoise Plenat

  DOI：10.1016/0040-4020(80)80151-7

  日期：1980.1

  Vicinal benzoyloxy-trans-bicyclo [2.2.1] heptanic bromhydrins, otherwise difficult to obtain are formed from N-bromosuccinimide and norbornanes bearing a 2-aryl-1,3 dioxolane skeleton. The greater stability of the intermediate dioxolenium ion reduces the tendency towards both Wagner-Meerwein rearrangement and neighbouring group participation by chlorine, processes usually observed when a less stable

  N-溴丁二酰亚胺和带有2-芳基-1,3-二氧戊环骨架的降冰片烷形成了否则难以获得的邻苯甲酰氧基-反式-双环[2.2.1]庚烷溴代醇。中间体二氧杂环丁烷离子的更高稳定性降低了瓦格纳-梅尔温重排和邻位氯参与的趋势，这是在涉及到稳定性较差的中间体时通常观察到的过程。然而，甲氧基羰基邻基的参与和瓦格纳·梅尔温重排分别发生在甲氧基羰基双环[2.2.1]庚烷和硼烷化合物中。
• Some Chlorine Derivatives of Norbornane (Bicyclo[2.2.1]heptane)
  作者：John D. Roberts、Frederick O. Johnson、Rudolph A. Carboni

  DOI：10.1021/ja01651a027

  日期：1954.11

  The endo-cis and trans-5,6-dichloronorbornenes were prepared by the respective additions of cis- and trans-dichlorocthylene to cyclopentadiene. The sterochemical assigments were confirmed by dipole moment studies. The cis-dichloride was inert to hydrolysis while the trans isomer was hydrolyzed to 3,5-dihydroxynortricyclene. Hydrogenation of the dichloride isomers gave the endo-cis- and trans-2,3-dichloronorbornanes

  内顺式和反式 5,6-二氯降冰片烯是通过将顺式和反式二氯乙烯分别加入环戊二烯来制备的。通过偶极矩研究证实了立体化学分配。顺式二氯化物对水解呈惰性，而反式异构体水解为 3,5-二羟基降三环烯。二氯化物异构体的氢化得到内-顺-和反-2,3-二氯降冰片烷。与基于卤化氢优先反式消除的预期相反，饱和的顺式二氯化物似乎比反式异构体更不容易脱卤化氢，尽管在两种情况下反应都很慢。两种异构体产生相同的脱卤化氢产物，2-氯降冰片烯，其结构通过氧化为顺式-环戊烷-1,3-二羧酸和水解为降樟脑而得到证实。降冰片烯在 - 75o 下氯化得到降三环基氯和 syn-7-exo-2-dichloronorbornane。由于化合物对脱卤化氢试剂的相对惰性，后者的结构被指定（优先于外-顺-2,3-二氯降冰片烷）。内-顺-2,3-二氯降冰片烷不容易水解，但反式-2,3-二氯降冰片烷和syn-7-exo-2-二氯降冰片烷分别水
• Solvolytic Reactivities of Nortricyclyl, Dehydronorbornyl and Norbornyl Halides. Possible Steric Requirements for Hyperconjugative Resonance¹
  作者：John D. Roberts、Winifred Bennett、Rose Armstrong

  DOI：10.1021/ja01164a001

  日期：1950.8

  the solvolytic reactivities of nortricyclyl (I), endo-dehydronorbornyl (II), exo-dehydronorbornyl (III), endonorbornyl (IV) and exo-norbornyl (V) halides. This series of structurally similar compounds provides an almost unique opportunity to observe the relationship between stereochemistry and solvolytic reactivities in alicyclic halides.

  本研究涉及对nortricyclyl (I)、endo-dehydronorbornyl (II)、exo-dehydronorbornyl (III)、endorbornyl (IV) 和exo-norbornyl (V) 卤化物的溶剂分解反应活性的测定和解释。这一系列结构相似的化合物提供了一个几乎独特的机会来观察脂环族卤化物中立体化学和溶剂分解反应性之间的关系。