3-乙酰氧基三环[2.2.1.02,6]庚烷 | 6555-48-2

• 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: 3-乙酰氧基三环[2.2.1.02,6]庚烷
• 英文名称: 3-Acetoxynortricyclen
• 英文别名: 3-acetoxy-tricyclo[2.2.1.0^2,6]heptane；tricyclo[2.2.1.02,6]heptan-3-yl acetate；nortricycl-5-yl acetate；3-acetoxynortricyclene；3-acetoxynortricyclane；acetic acid-(2,6-cyclo-norbornan-3-yl ester)；3-tricyclo[2.2.1.02,6]heptanyl acetate
• CAS: 6555-48-2；127127-98-4；127127-99-5
• 化学式: C₉H₁₂O₂
• 分子量: 152.193
• InChiKey: MIEOKFNJNHVJND-UHFFFAOYSA-N

物化性质

• 沸点：
  71.0-71.5 °C(Press: 8 Torr)
• 密度：
  1.0702 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-乙酰氧基三环[2.2.1.02,6]庚烷 在 jones' reagent 、 sodium methylate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 7.0h， 生成 三环[2.2.1.0(2,6)]庚烷-3-酮
  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
• 作为产物：
  描述：

  双环[2.2.1]庚-1-烯 在 lead(IV) acetate 、 苯 作用下， 生成 3-乙酰氧基三环[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

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。
• Kinetics and mechanism of addition of acids to olefins. Part I. Addition of acetic acid to cyclic and strained bicyclic olefins catalysed by trifluoromethanesulphonic acid
  作者：Roger M. G. Roberts

  DOI：10.1039/p29760001183

  日期：——

  The acid-catalysed addition of acetic acid to some cyclic and strained bicyclic olefins has been investigated using trifluoromethanesulphonic acid as the catalyst. For norbornene and related derivatives, the reaction rate was first order with respect to the catalyst acid but for cyclohexene there was evidence of a small contribution from a secondorder term. The addition was essentially non-stereospecific

  使用三氟甲磺酸作为催化剂，已经研究了乙酸在某些环状和应变双环烯烃中的酸催化加成反应。对于降冰片烯和相关衍生物，反应速率相对于催化剂酸是一阶的，但是对于环己烯，有证据表明二阶术语的贡献很小。该添加基本上是非立体特异性的。动力学同位素效应的值对于环状底物小于1，但对于降冰片烯则大于1，表明决定速率的质子转移发生了变化。报告激活参数以及CF 3 SO 3的酸度函数H 0的新值H在乙酸中。根据亲密的和溶剂分离的离子对讨论了加成反应。
• Acid-catalyzed hydrolysis of bridged bi- and tricyclic compounds. XXXVII. Kinetics and mechanisms of 1- and 3-acetoxynortricyclanes
  作者：Martti Lajunen、Rita Yli-Mannila、Outi Salminen

  DOI：10.1002/(sici)1099-1395(200002)13:2<133::aid-poc225>3.0.co;2-3

  日期：2000.2

  The disappearance of 1- and 3-nortricyclanols (1-OH and 2-OH) in aqueous perchloric acid was followed by capillary GC at different temperatures and acid concentrations. 1-OH is ca 1000 times more reactive than 2-OH. The activation parameters, solvent deuterium isotope effects and parameters of excess acidity equations were measured and the products were studied. Both isomeric nortricyclanols react

  在高氯酸水溶液中 1-和 3-去甲三环醇（1-OH 和 2-OH）消失后，在不同温度和酸浓度下进行毛细管 GC。1-OH 的反应性是 2-OH 的约 1000 倍。测定了活化参数、溶剂氘同位素效应和过量酸度方程参数，并对产物进行了研究。两种异构的去甲三环醇均根据 AdE2 机理反应，即环丙烷环在反应的速率决定阶段被质子化。在 1-OH 的情况下，质子化导致异构化，称为均酮化，其中 2-降冰片酮作为唯一的产物，在 2-OH 的情况下，水合，即形成羟基取代的降冰片基阳离子，通过水产生几种降冰片烷二醇。版权所有 © 2001 John Wiley & Sons, Ltd.
• An O-18 Tracer Study of the “Wet” and “Dry” Prevost Reactions
  作者：Kenneth B. Wiberg、Klaus A. Saegebarth

  DOI：10.1021/ja01580a038

  日期：1957.12
• Zyk, N. V.; Nikulin, A. V.; Kolbasenko, S. I., Journal of Organic Chemistry USSR (English Translation), 1984, p. 1881 - 1884
  作者：Zyk, N. V.、Nikulin, A. V.、Kolbasenko, S. I.、Zefirov, N. S.

  DOI：——

  日期：——