5-bromospiro[adamantane-2,2'-[1,3]dioxolane] | 74260-76-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-bromospiro[adamantane-2,2'-[1,3]dioxolane]
• 英文别名: 5-bromoadamantan-2-one ethylene ketal；1-bromoadaman-4-one ethylene ketal；1'-Bromospiro[1,3-dioxolane-2,4'-adamantane]；1'-bromospiro[1,3-dioxolane-2,4'-adamantane]
• CAS: 74260-76-7
• 化学式: C₁₂H₁₇BrO₂
• 分子量: 273.17
• InChiKey: KMFAWTUVKSTBNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-bromospiro[adamantane-2,2'-[1,3]dioxolane] 在 盐酸 、 水 作用下， 以 甲醇 、 乙醚 为溶剂， 反应 0.25h， 生成 5-(trimethylsilyl)adamantan-2-one
  参考文献：
  名称：

  Stereochemistry of reduction and methylation of 5-(trimethylsilyl)adamantan-2-one and 5-(trimethylstannyl)adamantan-2-one

  摘要：

  DOI：

  10.1021/jo00277a018
• 作为产物：
  描述：

  5-羟基-2-金刚烷酮 在 氢溴酸 、 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 16.0h， 生成 5-bromospiro[adamantane-2,2'-[1,3]dioxolane]
  参考文献：
  名称：

  Adamantane sulfone and sulfonamide 11-β-HSD1 Inhibitors

  摘要：

  Potent and selective adamantane sulfone and sulfonamide inhibitors of 11-beta-HSD-1 have been discovered. Selected compounds from these series have robust pharmacokinetic profiles and strongly inhibit liver, fat, and brain HSD1 for extended periods after oral dosing.

  DOI：

  10.1016/j.bmcl.2006.10.008

文献信息

• Synthesis of Substituted Adamantylzinc Reagents Using a Mg-Insertion in the Presence of ZnCl₂ and Further Functionalizations
  作者：Christoph Sämann、Vasudevan Dhayalan、Peter R. Schreiner、Paul Knochel

  DOI：10.1021/ol500781j

  日期：2014.5.2

  in the presence of ZnCl2 allows an efficient synthesis of adamantylzinc reagents starting from the corresponding functionalized tertiary bromides. The highly reactive adamantylzinc species readily undergo a broad variety of functionalizations such as Negishi cross-couplings, Cu(I)-catalyzed acylations and allylations, and 1,4-addition reactions leading to the expected products in excellent yields. Furthermore

  在ZnCl 2存在下通过LiCl介导的Mg插入可以从相应的官能化叔溴开始有效合成金刚烷基锌试剂。高反应性的金刚烷基锌类很容易经历各种各样的功能化，例如Negishi交叉偶联，Cu（I）催化的酰化和烯丙基化，以及1,4-加成反应，从而以预期的产率获得了预期的产物。此外，金刚烷基部分可以作为α-取代基引入对噻吩中，由于更高的亲脂性和防止π堆积而增加了其溶解度。
• WO2006/74244
  申请人：——

  公开号：——

  公开（公告）日：——
• Stereochemistry of reduction and methylation of 5-(trimethylsilyl)adamantan-2-one and 5-(trimethylstannyl)adamantan-2-one
  作者：Mei Xie、W. J. Le Noble

  DOI：10.1021/jo00277a018

  日期：1989.8
• Adamantane sulfone and sulfonamide 11-β-HSD1 Inhibitors
  作者：Bryan Sorensen、Martin Winn、Jeff Rohde、Qi Shuai、Jiahong Wang、Steven Fung、Katina Monzon、William Chiou、DeAnne Stolarik、Hovis Imade、Liping Pan、Xiaoqing Deng、Linda Chovan、Kenton Longenecker、Russell Judge、Wenying Qin、Michael Brune、Heidi Camp、Ernst U. Frevert、Peer Jacobson、J.T. Link

  DOI：10.1016/j.bmcl.2006.10.008

  日期：2007.1

  Potent and selective adamantane sulfone and sulfonamide inhibitors of 11-beta-HSD-1 have been discovered. Selected compounds from these series have robust pharmacokinetic profiles and strongly inhibit liver, fat, and brain HSD1 for extended periods after oral dosing.
• Reversal of Diastereoselectivities in Intra- and Intermolecular Reactions of 2-Adamantanylidenes Primarily Caused by Electron-Donating and Electron- Withdrawing Substituents on C5
  作者：Wolfgang Knoll、Michael M. Bobek、Hermann Kalchhauser、Murray G. Rosenberg、Udo H. Brinker

  DOI：10.1021/ol0350700

  日期：2003.8.1

  A reversal of diastereoselectivity was observed for novel 5-(trimethylsilyl)adamantan-2-ylidene (1c) with regard to 5-hydroxyadamantan-2-ylidene (1a). Ostensibly in intermolecular reactions, 5-substituted 2-adamantanylidenes (1) are sterically unbiased. However, inductive effects originating from the pendant group bend the divalent carbon bridge of 1 either toward (ERG's, e.g., -Si(CH3)(3)) or away from (EWG's, e.g., -OH) the gamma-position. Hence, the more exposed side is more susceptible to intermolecular reaction and the other side concomitantly undergoes intramolecular 1,3-CH insertions more readily.