3-(2-adamantyl)propionitrile | 113249-35-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-(2-adamantyl)propionitrile
• 英文别名: 2-(2-adamanthyl)ethylcyanide；3-(2-Adamantyl)propanenitrile
• CAS: 113249-35-7
• 化学式: C₁₃H₁₉N
• 分子量: 189.301
• InChiKey: KANSEWMVEJOUAE-UHFFFAOYSA-N

物化性质

• 沸点：
  318.2±11.0 °C(Predicted)
• 密度：
  1.012±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(2-adamantyl)propionitrile 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 生成 N-(adamantan-2-yl)propyl-4-methylbenzenesulfonamide
  参考文献：
  名称：

  Hofmann-Löffler流形内脂族CH键的多重卤化

  摘要：

  介绍了一种创新的脂族烃键位置选择性多卤化方法。该反应在Hofmann-Löffler流形中进行，酰胺基是唯一的介体，诱导选择性1,5-和1,6--氢原子转移，然后进行卤化。完成了多达四个固有CH键功能化的多次卤化事件。对于总共27个不同的实例（包括混合卤代），证明了这种新进入多卤代反应的广泛适用性以及由此产生的合成可能性。

  DOI：

  10.1002/chem.201804504
• 作为产物：
  描述：

  在 palladium on carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 3-(2-adamantyl)propionitrile
  参考文献：
  名称：

  Hofmann-Löffler流形内脂族CH键的多重卤化

  摘要：

  介绍了一种创新的脂族烃键位置选择性多卤化方法。该反应在Hofmann-Löffler流形中进行，酰胺基是唯一的介体，诱导选择性1,5-和1,6--氢原子转移，然后进行卤化。完成了多达四个固有CH键功能化的多次卤化事件。对于总共27个不同的实例（包括混合卤代），证明了这种新进入多卤代反应的广泛适用性以及由此产生的合成可能性。

  DOI：

  10.1002/chem.201804504

文献信息

• Hydrocarbon Activation. Synthesis of β-Cycloalkyl (Di)nitriles through Photosensitized Conjugate Radical Addition
  作者：Anna Maria Cardarelli、Maurizio Fagnoni、Mariella Mella、Angelo Albini

  DOI：10.1021/jo010400k

  日期：2001.11.1

  Photoinduced hydrogen abstraction from aliphatic cyclic hydrocarbons (C(5) to C(7), C(12), as well as adamantane) by triplet aromatic ketones in the presence of alpha,beta-unsaturated (di)nitriles offers a straightforward entry to the corresponding alkylated (di)nitriles via the alkyl radicals. Yields are moderate to good depending on the olefins structure (substitution in beta slows down the addition

  在存在α，β-不饱和（di）腈的情况下通过三重芳族酮从脂肪族环状烃（C（5）到C（7），C（12）以及金刚烷）的光诱导氢提取提供了直接的途径经由烷基的相应的烷基化的（二）腈。取决于烯烃的结构，产率中等至良好（β取代会减慢单腈的加成，但对于α，α-二腈，电子活化也可使β，β-二取代底物有效烷基化）。用（1-甲基戊-4-烯叉）丙二腈获得了串联烷基化-环化方法。
• Synthesis of adamantane derivatives by bridgehead radical addition to electron-deficient unsaturated bonds
  作者：Masatomi Ohno、Kenichi Ishizaki、Shoji Eguchi

  DOI：10.1021/jo00241a030

  日期：1988.3
• Evaluation of Antiproliferative Effect of N-(alkyladamantyl)phthalimides In vitro
  作者：Margareta Horvat、Lidija Uzelac、Marko Marjanović、Nikola Cindro、Oliver Franković、Kata Mlinarić-Majerski、Marijeta Kralj、Nikola Basarić

  DOI：10.1111/j.1747-0285.2011.01305.x

  日期：2012.4

  A series of (1‐adamantyl)phthalimides, 1–4, and (2‐adamantyl)phthalimides, 5–8, characterized by different chain length between the adamantyl and the phthalimide moiety were synthesized, as well as 1‐ and 2‐adamantylphthalimides substituted by nitro 9, 10, and amino group 11, 12, and phthalimides bearing homoadamantyl 13 and protoadamantyl substituent 14 and 15. The compounds were tested for antiproliferative activity in vitro on a series of five human cancer lines: MCF‐7 (breast carcinoma), SW 620 (colon carcinoma), HCT 116 (colon carcinoma), MOLT‐4 (acute lymphoblastic leukemia), H 460 (lung carcinoma), and a non‐tumor cell line HaCaT (human keratinocytes). All compounds except nitro derivatives 9 and 10 exhibited antiproliferative activity. The activity was generally better in the 2‐adamantyl series 5–8 and in the compounds having the longest alkyl spacers as in 4 and 8, or with an amino group as in 9 and 10. The most active compounds with the propylene spacer 4 and 8 showed the highest selectivity toward tumor cells. The activity was found to be due to a delay in the progress through the cell cycle at G1/S phase.
• Structure-based design of inhibitors of purine nucleoside phosphorylase. 2. 9-Alicyclic and 9-heteroalicyclic derivatives of 9-deazaguanine
  作者：John A. Secrist、Shri Niwas、Jerry D. Rose、Y. Sudhakar Babu、Charles E. Bugg、Mark D. Erion、Wayne C. Guida、Steven E. Ealick、John A. Montgomery

  DOI：10.1021/jm00065a007

  日期：1993.6

  Alicyclic and heteroalicyclic derivatives of 9-deazaguanine (2-amino-1,5-dihydro-4H-pyrrolo[3,2-d][pyrimidin-4-one) d] [pyrimidin-4-one) are, with one exception, potent inhibitors of purine nucleoside phosphorylase (PNP) equaling the corresponding 9-arylmethyl derivatives previously investigated. The mode of binding of these compounds to PNP was determined by X-ray crystallography.
• EP0500653A4
  申请人：——

  公开号：EP0500653A4

  公开（公告）日：1995-08-23